# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mk568al
_database_code_depnum_ccdc_archive 'CCDC 1440298'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O2'
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.6624(4)
_cell_length_b                   13.0517(9)
_cell_length_c                   15.2377(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.888(4)
_cell_angle_gamma                90
_cell_volume                     1105.86(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21550
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       bloc
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'long-fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            10410
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.071
_diffrn_reflns_theta_max         27.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2522
_reflns_number_gt                2026
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0402P)²+0.2285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2522
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C -0.0842(2) 0.60024(9) 0.10844(8) 0.0263(3) Uani 1 1 d . . . . .
C2 C -0.1664(2) 0.68803(10) 0.06117(8) 0.0319(3) Uani 1 1 d . . . . .
C3 C -0.0121(3) 0.77086(10) 0.06481(9) 0.0352(3) Uani 1 1 d . . . . .
C4 C 0.2195(3) 0.76578(10) 0.11400(9) 0.0344(3) Uani 1 1 d . . . . .
C5 C 0.2978(2) 0.67696(10) 0.16109(8) 0.0289(3) Uani 1 1 d . . . . .
C6 C 0.1461(2) 0.59319(9) 0.15989(7) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.2150(2) 0.49501(9) 0.20990(8) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.1053(2) 0.40679(9) 0.14847(8) 0.0242(3) Uani 1 1 d . . . . .
C9 C -0.1635(2) 0.42048(10) 0.12332(8) 0.0280(3) Uani 1 1 d . . . . .
C10 C 0.1715(2) 0.29993(10) 0.18453(9) 0.0299(3) Uani 1 1 d . . . . .
C11 C 0.1294(2) 0.49345(10) 0.29989(8) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.2464(2) 0.57464(10) 0.36664(8) 0.0265(3) Uani 1 1 d . . . . .
C13 C 0.5037(2) 0.55519(9) 0.39715(7) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.70416(19) 0.53755(9) 0.42032(7) 0.0334(3) Uani 1 1 d . . . . .
O1 O -0.24664(15) 0.51849(7) 0.10367(6) 0.0308(2) Uani 1 1 d . . . . .
O2 O -0.31122(15) 0.35382(7) 0.11898(6) 0.0374(3) Uani 1 1 d . . . . .
H2 H -0.333(3) 0.6870(12) 0.0260(10) 0.045(4) Uiso 1 1 d . . . . .
H3 H -0.065(3) 0.8320(12) 0.0316(10) 0.038(4) Uiso 1 1 d . . . . .
H4 H 0.332(3) 0.8251(12) 0.1159(10) 0.038(4) Uiso 1 1 d . . . . .
H5 H 0.464(2) 0.6728(10) 0.1958(9) 0.029(3) Uiso 1 1 d . . . . .
H7 H 0.388(2) 0.4867(9) 0.2203(8) 0.022(3) Uiso 1 1 d . . . . .
H8 H 0.165(2) 0.4159(10) 0.0929(9) 0.028(3) Uiso 1 1 d . . . . .
H10A H 0.120(3) 0.2468(12) 0.1379(11) 0.045(4) Uiso 1 1 d . . . . .
H10B H 0.095(2) 0.2853(11) 0.2350(10) 0.035(4) Uiso 1 1 d . . . . .
H10C H 0.350(3) 0.2963(11) 0.2031(9) 0.039(4) Uiso 1 1 d . . . . .
H11A H 0.157(2) 0.4233(10) 0.3270(9) 0.029(3) Uiso 1 1 d . . . . .
H11B H -0.046(3) 0.5062(10) 0.2893(9) 0.030(3) Uiso 1 1 d . . . . .
H12A H 0.172(3) 0.5731(11) 0.4195(10) 0.038(4) Uiso 1 1 d . . . . .
H12B H 0.228(2) 0.6451(11) 0.3406(9) 0.033(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3863(18) . ?
C1 C6 1.3917(17) . ?
C1 O1 1.4018(15) . ?
C2 C3 1.384(2) . ?
C2 H2 0.991(16) . ?
C3 C4 1.384(2) . ?
C3 H3 0.963(15) . ?
C4 C5 1.3911(18) . ?
C4 H4 0.999(15) . ?
C5 C6 1.3883(17) . ?
C5 H5 0.992(14) . ?
C6 C7 1.5041(16) . ?
C7 C11 1.5384(16) . ?
C7 C8 1.5388(16) . ?
C7 H7 0.968(13) . ?
C8 C9 1.5081(17) . ?
C8 C10 1.5198(18) . ?
C8 H8 0.977(14) . ?
C9 O2 1.2001(15) . ?
C9 O1 1.3764(15) . ?
C10 H10A 0.996(17) . ?
C10 H10B 0.969(15) . ?
C10 H10C 1.000(15) . ?
C11 C12 1.5303(17) . ?
C11 H11A 1.004(14) . ?
C11 H11B 0.991(14) . ?
C12 C13 1.4654(17) . ?
C12 H12A 0.978(15) . ?
C12 H12B 0.999(14) . ?
C13 N1 1.1464(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.31(12) . . ?
C2 C1 O1 116.70(11) . . ?
C6 C1 O1 120.98(11) . . ?
C3 C2 C1 118.49(12) . . ?
C3 C2 H2 124.0(9) . . ?
C1 C2 H2 117.5(9) . . ?
C4 C3 C2 120.71(12) . . ?
C4 C3 H3 119.7(9) . . ?
C2 C3 H3 119.6(9) . . ?
C3 C4 C5 119.76(13) . . ?
C3 C4 H4 120.8(8) . . ?
C5 C4 H4 119.5(9) . . ?
C6 C5 C4 120.90(12) . . ?
C6 C5 H5 119.2(8) . . ?
C4 C5 H5 119.9(8) . . ?
C5 C6 C1 117.82(11) . . ?
C5 C6 C7 124.32(11) . . ?
C1 C6 C7 117.86(10) . . ?
C6 C7 C11 111.57(10) . . ?
C6 C7 C8 107.05(9) . . ?
C11 C7 C8 111.93(9) . . ?
C6 C7 H7 109.6(7) . . ?
C11 C7 H7 109.4(7) . . ?
C8 C7 H7 107.1(7) . . ?
C9 C8 C10 111.65(10) . . ?
C9 C8 C7 109.74(10) . . ?
C10 C8 C7 115.03(10) . . ?
C9 C8 H8 105.3(8) . . ?
C10 C8 H8 108.8(8) . . ?
C7 C8 H8 105.6(8) . . ?
O2 C9 O1 117.09(11) . . ?
O2 C9 C8 125.99(12) . . ?
O1 C9 C8 116.92(10) . . ?
C8 C10 H10A 111.2(9) . . ?
C8 C10 H10B 110.6(8) . . ?
H10A C10 H10B 108.4(12) . . ?
C8 C10 H10C 108.3(8) . . ?
H10A C10 H10C 108.1(12) . . ?
H10B C10 H10C 110.2(11) . . ?
C12 C11 C7 114.43(10) . . ?
C12 C11 H11A 110.2(8) . . ?
C7 C11 H11A 109.2(8) . . ?
C12 C11 H11B 106.7(8) . . ?
C7 C11 H11B 109.2(8) . . ?
H11A C11 H11B 106.9(11) . . ?
C13 C12 C11 111.76(10) . . ?
C13 C12 H12A 107.1(8) . . ?
C11 C12 H12A 109.4(8) . . ?
C13 C12 H12B 107.9(8) . . ?
C11 C12 H12B 112.0(8) . . ?
H12A C12 H12B 108.5(11) . . ?
N1 C13 C12 178.32(13) . . ?
C9 O1 C1 120.13(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
C6 C1 C2 C3 0.74(18) . . . . ?
O1 C1 C2 C3 179.42(10) . . . . ?
C1 C2 C3 C4 0.47(18) . . . . ?
C2 C3 C4 C5 -0.66(19) . . . . ?
C3 C4 C5 C6 -0.35(19) . . . . ?
C4 C5 C6 C1 1.49(17) . . . . ?
C4 C5 C6 C7 -179.06(11) . . . . ?
C2 C1 C6 C5 -1.71(17) . . . . ?
O1 C1 C6 C5 179.67(10) . . . . ?
C2 C1 C6 C7 178.81(10) . . . . ?
O1 C1 C6 C7 0.19(16) . . . . ?
C5 C6 C7 C11 96.70(13) . . . . ?
C1 C6 C7 C11 -83.85(13) . . . . ?
C5 C6 C7 C8 -140.53(11) . . . . ?
C1 C6 C7 C8 38.92(13) . . . . ?
C6 C7 C8 C9 -57.67(12) . . . . ?
C11 C7 C8 C9 64.88(13) . . . . ?
C6 C7 C8 C10 175.45(10) . . . . ?
C11 C7 C8 C10 -62.00(13) . . . . ?
C10 C8 C9 O2 -10.21(18) . . . . ?
C7 C8 C9 O2 -138.97(13) . . . . ?
C10 C8 C9 O1 169.70(10) . . . . ?
C7 C8 C9 O1 40.94(14) . . . . ?
C6 C7 C11 C12 -64.31(13) . . . . ?
C8 C7 C11 C12 175.75(10) . . . . ?
C7 C11 C12 C13 -67.04(14) . . . . ?
O2 C9 O1 C1 179.24(11) . . . . ?
C8 C9 O1 C1 -0.67(15) . . . . ?
C2 C1 O1 C9 159.38(10) . . . . ?
C6 C1 O1 C9 -21.92(16) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_mk569al
_database_code_depnum_ccdc_archive 'CCDC 1440299'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O'
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.44

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4307(6)
_cell_length_b                   17.1837(5)
_cell_length_c                   11.8533(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.937(2)
_cell_angle_gamma                90
_cell_volume                     1919.78(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8023
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'long-fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            19028
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.088
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4396
_reflns_number_gt                2581
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0082(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4396
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
C1 C 0.83367(17) 0.26937(8) 0.28289(13) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.87006(19) 0.30371(9) 0.17990(15) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.85507(19) 0.38300(9) 0.16441(15) 0.0287(4) Uani 1 1 d . . . . .
C4 C 0.80351(19) 0.43086(9) 0.24861(14) 0.0285(4) Uani 1 1 d . . . . .
C5 C 0.76664(19) 0.39842(9) 0.34909(15) 0.0260(4) Uani 1 1 d . . . . .
C6 C 0.77927(17) 0.31780(8) 0.36802(13) 0.0227(4) Uani 1 1 d . . . . .
C7 C 0.73202(17) 0.28433(8) 0.47369(14) 0.0235(4) Uani 1 1 d . . . . .
C8 C 0.71780(18) 0.19647(8) 0.47482(14) 0.0230(4) Uani 1 1 d . . . . .
C9 C 0.84757(18) 0.16212(9) 0.41776(14) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.9891(2) 0.18144(9) 0.48002(15) 0.0273(4) Uani 1 1 d . . . . .
C11 C 0.9938(2) 0.16067(9) 0.60601(16) 0.0318(4) Uani 1 1 d . . . . .
C12 C 0.9569(2) 0.07921(10) 0.62487(14) 0.0325(4) Uani 1 1 d . . . . .
C13 C 0.57853(18) 0.16979(8) 0.41735(13) 0.0236(4) Uani 1 1 d . . . . .
C14 C 0.47612(19) 0.22186(9) 0.37624(14) 0.0272(4) Uani 1 1 d . . . . .
C15 C 0.3531(2) 0.19526(10) 0.32177(15) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.3290(2) 0.11628(9) 0.30842(15) 0.0315(4) Uani 1 1 d . . . . .
C17 C 0.42797(19) 0.06399(9) 0.35242(14) 0.0287(4) Uani 1 1 d . . . . .
C18 C 0.55074(19) 0.09037(9) 0.40643(14) 0.0260(4) Uani 1 1 d . . . . .
C19 C 0.9175(2) 0.14167(9) 0.21778(14) 0.0258(4) Uani 1 1 d . . . . .
C20 C 0.82160(19) 0.11940(8) 0.11744(14) 0.0256(4) Uani 1 1 d . . . . .
C21 C 0.6749(2) 0.12624(9) 0.11849(15) 0.0283(4) Uani 1 1 d . . . . .
C22 C 0.5907(2) 0.10155(9) 0.02667(16) 0.0335(5) Uani 1 1 d . . . . .
C23 C 0.6523(2) 0.07097(10) -0.06785(16) 0.0382(5) Uani 1 1 d . . . . .
C24 C 0.7990(2) 0.06435(10) -0.07023(16) 0.0366(5) Uani 1 1 d . . . . .
C25 C 0.8832(2) 0.08850(9) 0.02192(15) 0.0299(4) Uani 1 1 d . . . . .
N1 N 0.92630(19) 0.01542(9) 0.63680(14) 0.0471(5) Uani 1 1 d . . . . .
N2 N 0.84942(15) 0.19028(7) 0.30091(11) 0.0237(3) Uani 1 1 d . . . . .
O1 O 0.70209(13) 0.32371(6) 0.55619(10) 0.0297(3) Uani 1 1 d . . . . .
H2 H 0.9087(17) 0.2718(8) 0.1186(13) 0.020(4) Uiso 1 1 d . . . . .
H3 H 0.8826(19) 0.4046(9) 0.0908(15) 0.029(4) Uiso 1 1 d . . . . .
H4 H 0.7958(19) 0.4881(10) 0.2376(14) 0.035(5) Uiso 1 1 d . . . . .
H5 H 0.7289(18) 0.4309(9) 0.4092(14) 0.027(4) Uiso 1 1 d . . . . .
H8 H 0.7184(17) 0.1791(8) 0.5558(14) 0.021(4) Uiso 1 1 d . . . . .
H9 H 0.8363(16) 0.1026(8) 0.4130(12) 0.018(4) Uiso 1 1 d . . . . .
H10A H 1.0101(19) 0.2394(10) 0.4727(14) 0.036(5) Uiso 1 1 d . . . . .
H10B H 1.0691(19) 0.1518(9) 0.4450(14) 0.028(4) Uiso 1 1 d . . . . .
H11A H 0.927(2) 0.1952(10) 0.6475(15) 0.036(5) Uiso 1 1 d . . . . .
H11B H 1.094(2) 0.1702(10) 0.6405(16) 0.045(5) Uiso 1 1 d . . . . .
H14 H 0.4903(18) 0.2774(10) 0.3843(13) 0.031(5) Uiso 1 1 d . . . . .
H15 H 0.283(2) 0.2319(10) 0.2971(15) 0.039(5) Uiso 1 1 d . . . . .
H16 H 0.243(2) 0.0987(9) 0.2679(15) 0.037(5) Uiso 1 1 d . . . . .
H17 H 0.4106(18) 0.0079(10) 0.3434(13) 0.032(5) Uiso 1 1 d . . . . .
H18 H 0.6231(18) 0.0531(9) 0.4392(13) 0.025(4) Uiso 1 1 d . . . . .
H19A H 1.0049(19) 0.1668(8) 0.1871(14) 0.023(4) Uiso 1 1 d . . . . .
H19B H 0.9520(18) 0.0935(9) 0.2560(13) 0.026(4) Uiso 1 1 d . . . . .
H21 H 0.6279(18) 0.1494(8) 0.1880(14) 0.024(4) Uiso 1 1 d . . . . .
H22 H 0.487(2) 0.1065(10) 0.0309(16) 0.043(6) Uiso 1 1 d . . . . .
H23 H 0.591(2) 0.0537(10) -0.1331(16) 0.051(6) Uiso 1 1 d . . . . .
H24 H 0.846(2) 0.0427(10) -0.1381(17) 0.051(6) Uiso 1 1 d . . . . .
H25 H 0.988(2) 0.0811(9) 0.0209(15) 0.036(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.3830(18) . ?
C1 C2 1.409(2) . ?
C1 C6 1.417(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.989(16) . ?
C3 C4 1.394(2) . ?
C3 H3 0.991(18) . ?
C4 C5 1.370(2) . ?
C4 H4 0.995(16) . ?
C5 C6 1.408(2) . ?
C5 H5 0.982(17) . ?
C6 C7 1.461(2) . ?
C7 O1 1.2298(19) . ?
C7 C8 1.516(2) . ?
C8 C13 1.529(2) . ?
C8 C9 1.536(2) . ?
C8 H8 1.005(16) . ?
C9 N2 1.468(2) . ?
C9 C10 1.539(2) . ?
C9 H9 1.029(14) . ?
C10 C11 1.535(2) . ?
C10 H10A 1.020(16) . ?
C10 H10B 1.010(18) . ?
C11 C12 1.461(2) . ?
C11 H11A 1.006(19) . ?
C11 H11B 1.03(2) . ?
C12 N1 1.143(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.395(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.968(16) . ?
C15 C16 1.384(2) . ?
C15 H15 0.951(18) . ?
C16 C17 1.384(2) . ?
C16 H16 0.975(19) . ?
C17 C18 1.380(2) . ?
C17 H17 0.983(16) . ?
C18 H18 1.005(16) . ?
C19 N2 1.457(2) . ?
C19 C20 1.519(2) . ?
C19 H19A 1.008(18) . ?
C19 H19B 0.992(15) . ?
C20 C21 1.389(3) . ?
C20 C25 1.395(2) . ?
C21 C22 1.392(2) . ?
C21 H21 1.029(17) . ?
C22 C23 1.383(3) . ?
C22 H22 0.99(2) . ?
C23 C24 1.390(3) . ?
C23 H23 0.996(19) . ?
C24 C25 1.392(3) . ?
C24 H24 1.00(2) . ?
C25 H25 0.99(2) . ?

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
N2 C1 C2 121.16(14) . . ?
N2 C1 C6 120.43(14) . . ?
C2 C1 C6 118.40(13) . . ?
C3 C2 C1 120.10(16) . . ?
C3 C2 H2 119.2(9) . . ?
C1 C2 H2 120.7(9) . . ?
C2 C3 C4 121.57(16) . . ?
C2 C3 H3 117.3(9) . . ?
C4 C3 H3 121.1(9) . . ?
C5 C4 C3 119.16(15) . . ?
C5 C4 H4 119.8(10) . . ?
C3 C4 H4 121.0(10) . . ?
C4 C5 C6 121.07(16) . . ?
C4 C5 H5 120.5(9) . . ?
C6 C5 H5 118.4(9) . . ?
C5 C6 C1 119.67(15) . . ?
C5 C6 C7 119.81(15) . . ?
C1 C6 C7 120.49(13) . . ?
O1 C7 C6 123.36(14) . . ?
O1 C7 C8 121.21(15) . . ?
C6 C7 C8 115.41(14) . . ?
C7 C8 C13 111.68(12) . . ?
C7 C8 C9 107.87(14) . . ?
C13 C8 C9 111.95(13) . . ?
C7 C8 H8 107.9(8) . . ?
C13 C8 H8 108.3(9) . . ?
C9 C8 H8 109.1(9) . . ?
N2 C9 C8 108.90(13) . . ?
N2 C9 C10 110.09(14) . . ?
C8 C9 C10 113.38(14) . . ?
N2 C9 H9 106.3(8) . . ?
C8 C9 H9 108.9(9) . . ?
C10 C9 H9 109.1(8) . . ?
C11 C10 C9 114.35(15) . . ?
C11 C10 H10A 108.1(10) . . ?
C9 C10 H10A 109.7(10) . . ?
C11 C10 H10B 106.6(9) . . ?
C9 C10 H10B 110.0(9) . . ?
H10A C10 H10B 107.9(14) . . ?
C12 C11 C10 111.87(14) . . ?
C12 C11 H11A 109.5(10) . . ?
C10 C11 H11A 109.9(10) . . ?
C12 C11 H11B 108.1(10) . . ?
C10 C11 H11B 110.2(11) . . ?
H11A C11 H11B 107.0(14) . . ?
N1 C12 C11 178.16(19) . . ?
C14 C13 C18 118.06(16) . . ?
C14 C13 C8 122.57(13) . . ?
C18 C13 C8 119.36(14) . . ?
C15 C14 C13 120.72(15) . . ?
C15 C14 H14 118.8(10) . . ?
C13 C14 H14 120.5(10) . . ?
C16 C15 C14 120.52(17) . . ?
C16 C15 H15 120.4(11) . . ?
C14 C15 H15 119.0(11) . . ?
C15 C16 C17 119.18(17) . . ?
C15 C16 H16 119.4(10) . . ?
C17 C16 H16 121.5(10) . . ?
C18 C17 C16 120.36(15) . . ?
C18 C17 H17 120.4(10) . . ?
C16 C17 H17 119.2(10) . . ?
C17 C18 C13 121.08(16) . . ?
C17 C18 H18 121.2(9) . . ?
C13 C18 H18 117.7(9) . . ?
N2 C19 C20 114.15(14) . . ?
N2 C19 H19A 112.5(9) . . ?
C20 C19 H19A 107.3(9) . . ?
N2 C19 H19B 108.3(9) . . ?
C20 C19 H19B 108.9(9) . . ?
H19A C19 H19B 105.2(13) . . ?
C21 C20 C25 118.78(16) . . ?
C21 C20 C19 122.61(16) . . ?
C25 C20 C19 118.57(17) . . ?
C20 C21 C22 120.64(18) . . ?
C20 C21 H21 119.8(9) . . ?
C22 C21 H21 119.6(9) . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 121.2(11) . . ?
C21 C22 H22 118.4(11) . . ?
C22 C23 C24 119.56(18) . . ?
C22 C23 H23 119.6(12) . . ?
C24 C23 H23 120.9(12) . . ?
C23 C24 C25 120.10(19) . . ?
C23 C24 H24 120.9(11) . . ?
C25 C24 H24 119.0(11) . . ?
C24 C25 C20 120.57(19) . . ?
C24 C25 H25 119.4(10) . . ?
C20 C25 H25 119.9(10) . . ?
C1 N2 C19 120.41(13) . . ?
C1 N2 C9 117.72(12) . . ?
C19 N2 C9 117.94(12) . . ?

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
N2 C1 C2 C3 -179.18(15) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C4 C5 C6 C7 -176.73(15) . . . . ?
N2 C1 C6 C5 178.72(14) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N2 C1 C6 C7 -3.3(2) . . . . ?
C2 C1 C6 C7 176.32(15) . . . . ?
C5 C6 C7 O1 -12.1(2) . . . . ?
C1 C6 C7 O1 169.84(15) . . . . ?
C5 C6 C7 C8 166.22(14) . . . . ?
C1 C6 C7 C8 -11.8(2) . . . . ?
O1 C7 C8 C13 98.03(17) . . . . ?
C6 C7 C8 C13 -80.38(18) . . . . ?
O1 C7 C8 C9 -138.56(15) . . . . ?
C6 C7 C8 C9 43.03(18) . . . . ?
C7 C8 C9 N2 -60.76(16) . . . . ?
C13 C8 C9 N2 62.50(16) . . . . ?
C7 C8 C9 C10 62.17(16) . . . . ?
C13 C8 C9 C10 -174.57(12) . . . . ?
N2 C9 C10 C11 175.07(13) . . . . ?
C8 C9 C10 C11 52.80(18) . . . . ?
C9 C10 C11 C12 54.3(2) . . . . ?
C7 C8 C13 C14 -3.6(2) . . . . ?
C9 C8 C13 C14 -124.71(16) . . . . ?
C7 C8 C13 C18 177.24(15) . . . . ?
C9 C8 C13 C18 56.17(19) . . . . ?
C18 C13 C14 C15 -2.7(2) . . . . ?
C8 C13 C14 C15 178.12(16) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 2.6(2) . . . . ?
C8 C13 C18 C17 -178.26(16) . . . . ?
N2 C19 C20 C21 -16.5(2) . . . . ?
N2 C19 C20 C25 165.67(14) . . . . ?
C25 C20 C21 C22 1.0(2) . . . . ?
C19 C20 C21 C22 -176.81(14) . . . . ?
C20 C21 C22 C23 -1.1(2) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.1(2) . . . . ?
C21 C20 C25 C24 -0.6(2) . . . . ?
C19 C20 C25 C24 177.38(14) . . . . ?
C2 C1 N2 C19 6.2(2) . . . . ?
C6 C1 N2 C19 -174.23(14) . . . . ?
C2 C1 N2 C9 163.45(15) . . . . ?
C6 C1 N2 C9 -17.0(2) . . . . ?
C20 C19 N2 C1 -79.85(19) . . . . ?
C20 C19 N2 C9 122.95(15) . . . . ?
C8 C9 N2 C1 49.57(18) . . . . ?
C10 C9 N2 C1 -75.31(18) . . . . ?
C8 C9 N2 C19 -152.61(14) . . . . ?
C10 C9 N2 C19 82.51(17) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.075

