# 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_mo_60304b
_database_code_depnum_ccdc_archive 'CCDC 1480918'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-11 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         ?
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39

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                   8.9320(15)
_cell_length_b                   6.9867(12)
_cell_length_c                   27.957(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.869(3)
_cell_angle_gamma                90
_cell_volume                     1732.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6528
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.33

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.700
_exptl_crystal_size_min          0.480
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11839
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         27.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3876
_reflns_number_gt                3275
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0731P)²+0.6763P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3876
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1442
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 -0.19438(16) -0.51546(17) 0.46665(4) 0.0469(3) Uani 1 1 d . . . . .
N1 N 0.05912(13) 0.34852(17) 0.31631(4) 0.0280(3) Uani 1 1 d . . . . .
C1 C -0.08479(16) 0.3433(2) 0.29270(5) 0.0276(3) Uani 1 1 d . . . . .
C2 C -0.15091(18) 0.4521(2) 0.25373(5) 0.0326(3) Uani 1 1 d . . . . .
H2 H -0.0954 0.5443 0.2388 0.039 Uiso 1 1 calc R U . . .
C3 C -0.30146(18) 0.4181(2) 0.23811(6) 0.0378(4) Uani 1 1 d . . . . .
H3 H -0.3492 0.4885 0.2119 0.045 Uiso 1 1 calc R U . . .
C4 C -0.38469(18) 0.2807(3) 0.26046(6) 0.0387(4) Uani 1 1 d . . . . .
H4 H -0.4873 0.2628 0.2494 0.046 Uiso 1 1 calc R U . . .
C5 C -0.31836(17) 0.1715(2) 0.29837(5) 0.0331(3) Uani 1 1 d . . . . .
H5 H -0.3748 0.0793 0.3130 0.040 Uiso 1 1 calc R U . . .
C6 C -0.16506(16) 0.2003(2) 0.31479(5) 0.0275(3) Uani 1 1 d . . . . .
C7 C -0.06248(16) 0.1150(2) 0.35219(5) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.07411(16) 0.20838(19) 0.35184(5) 0.0271(3) Uani 1 1 d . . . . .
C9 C 0.22328(16) 0.1828(2) 0.37919(5) 0.0302(3) Uani 1 1 d . . . . .
C10 C 0.26231(19) 0.0181(2) 0.40641(6) 0.0398(4) Uani 1 1 d . . . . .
H10 H 0.1912 -0.0803 0.4078 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4055(2) -0.0003(3) 0.43138(7) 0.0536(5) Uani 1 1 d . . . . .
H11 H 0.4308 -0.1112 0.4496 0.064 Uiso 1 1 calc R U . . .
C12 C 0.5112(2) 0.1436(4) 0.42957(8) 0.0576(5) Uani 1 1 d . . . . .
H12 H 0.6077 0.1312 0.4468 0.069 Uiso 1 1 calc R U . . .
C13 C 0.4746(2) 0.3052(3) 0.40237(7) 0.0498(5) Uani 1 1 d . . . . .
H13 H 0.5471 0.4018 0.4009 0.060 Uiso 1 1 calc R U . . .
C14 C 0.33194(18) 0.3274(2) 0.37708(6) 0.0364(4) Uani 1 1 d . . . . .
C15 C 0.2900(2) 0.5053(3) 0.34826(7) 0.0462(4) Uani 1 1 d . . . . .
H15A H 0.3817 0.5660 0.3394 0.055 Uiso 1 1 calc R U . . .
H15B H 0.2408 0.5960 0.3681 0.055 Uiso 1 1 calc R U . . .
C16 C 0.18497(18) 0.4610(2) 0.30302(6) 0.0367(4) Uani 1 1 d . . . . .
H16A H 0.1478 0.5801 0.2874 0.044 Uiso 1 1 calc R U . . .
H16B H 0.2389 0.3888 0.2804 0.044 Uiso 1 1 calc R U . . .
C17 C -0.09982(16) -0.0451(2) 0.38347(5) 0.0272(3) Uani 1 1 d . . . . .
C18 C -0.10926(17) -0.0212(2) 0.43228(5) 0.0309(3) Uani 1 1 d . . . . .
H18 H -0.0932 0.1010 0.4460 0.037 Uiso 1 1 calc R U . . .
C19 C -0.14185(18) -0.1732(2) 0.46144(5) 0.0331(3) Uani 1 1 d . . . . .
H19 H -0.1478 -0.1536 0.4944 0.040 Uiso 1 1 calc R U . . .
C20 C -0.16544(17) -0.3537(2) 0.44153(5) 0.0325(3) Uani 1 1 d . . . . .
C21 C -0.1590(2) -0.3805(2) 0.39256(6) 0.0416(4) Uani 1 1 d . . . . .
H21 H -0.1763 -0.5025 0.3788 0.050 Uiso 1 1 calc R U . . .
C22 C -0.1272(2) -0.2277(2) 0.36403(5) 0.0381(4) Uani 1 1 d . . . . .
H22 H -0.1239 -0.2470 0.3309 0.046 Uiso 1 1 calc R U . . .
C23 C -0.2170(3) -0.4917(3) 0.51585(7) 0.0567(5) Uani 1 1 d . . . . .
H23A H -0.1281 -0.4339 0.5333 0.085 Uiso 1 1 calc R U . . .
H23B H -0.2350 -0.6155 0.5298 0.085 Uiso 1 1 calc R U . . .
H23C H -0.3035 -0.4094 0.5179 0.085 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 C20 1.3714(18) . ?
O1 C23 1.424(2) . ?
N1 C1 1.3734(18) . ?
N1 C8 1.3898(18) . ?
N1 C16 1.4555(18) . ?
C1 C2 1.400(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.406(2) . ?
C4 C5 1.381(2) . ?
C5 C6 1.406(2) . ?
C6 C7 1.435(2) . ?
C7 C8 1.384(2) . ?
C7 C17 1.4824(19) . ?
C8 C9 1.466(2) . ?
C9 C10 1.400(2) . ?
C9 C14 1.407(2) . ?
C10 C11 1.388(2) . ?
C11 C12 1.385(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.390(2) . ?
C14 C15 1.504(2) . ?
C15 C16 1.514(2) . ?
C17 C18 1.3873(19) . ?
C17 C22 1.397(2) . ?
C18 C19 1.391(2) . ?
C19 C20 1.384(2) . ?
C20 C21 1.390(2) . ?
C21 C22 1.382(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
C20 O1 C23 117.13(14) . . ?
C1 N1 C8 109.22(11) . . ?
C1 N1 C16 126.78(12) . . ?
C8 N1 C16 123.46(12) . . ?
N1 C1 C2 130.00(13) . . ?
N1 C1 C6 107.67(12) . . ?
C2 C1 C6 122.33(14) . . ?
C3 C2 C1 117.12(14) . . ?
C2 C3 C4 121.50(14) . . ?
C5 C4 C3 121.17(15) . . ?
C4 C5 C6 118.88(14) . . ?
C5 C6 C1 118.95(13) . . ?
C5 C6 C7 133.67(13) . . ?
C1 C6 C7 107.38(12) . . ?
C8 C7 C6 106.60(12) . . ?
C8 C7 C17 128.33(13) . . ?
C6 C7 C17 125.05(13) . . ?
C7 C8 N1 109.10(12) . . ?
C7 C8 C9 133.29(13) . . ?
N1 C8 C9 117.56(12) . . ?
C10 C9 C14 118.99(14) . . ?
C10 C9 C8 122.37(14) . . ?
C14 C9 C8 118.62(14) . . ?
C11 C10 C9 120.28(16) . . ?
C12 C11 C10 120.38(18) . . ?
C13 C12 C11 119.80(17) . . ?
C12 C13 C14 120.98(18) . . ?
C13 C14 C9 119.56(16) . . ?
C13 C14 C15 121.27(16) . . ?
C9 C14 C15 119.15(14) . . ?
C14 C15 C16 111.59(14) . . ?
N1 C16 C15 108.51(13) . . ?
C18 C17 C22 117.66(13) . . ?
C18 C17 C7 122.28(12) . . ?
C22 C17 C7 120.06(12) . . ?
C17 C18 C19 121.76(13) . . ?
C20 C19 C18 119.50(13) . . ?
O1 C20 C19 125.01(13) . . ?
O1 C20 C21 115.23(14) . . ?
C19 C20 C21 119.76(14) . . ?
C22 C21 C20 120.01(14) . . ?
C21 C22 C17 121.28(14) . . ?

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
C8 N1 C1 C2 -177.95(14) . . . . ?
C16 N1 C1 C2 -6.2(2) . . . . ?
C8 N1 C1 C6 1.94(15) . . . . ?
C16 N1 C1 C6 173.70(13) . . . . ?
N1 C1 C2 C3 -178.37(14) . . . . ?
C6 C1 C2 C3 1.8(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C4 C5 C6 C7 -179.93(15) . . . . ?
N1 C1 C6 C5 177.48(12) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
N1 C1 C6 C7 -1.46(15) . . . . ?
C2 C1 C6 C7 178.44(13) . . . . ?
C5 C6 C7 C8 -178.28(15) . . . . ?
C1 C6 C7 C8 0.44(15) . . . . ?
C5 C6 C7 C17 3.0(2) . . . . ?
C1 C6 C7 C17 -178.25(13) . . . . ?
C6 C7 C8 N1 0.74(15) . . . . ?
C17 C7 C8 N1 179.38(13) . . . . ?
C6 C7 C8 C9 -176.71(14) . . . . ?
C17 C7 C8 C9 1.9(3) . . . . ?
C1 N1 C8 C7 -1.69(15) . . . . ?
C16 N1 C8 C7 -173.78(13) . . . . ?
C1 N1 C8 C9 176.21(12) . . . . ?
C16 N1 C8 C9 4.1(2) . . . . ?
C7 C8 C9 C10 14.3(2) . . . . ?
N1 C8 C9 C10 -162.98(14) . . . . ?
C7 C8 C9 C14 -167.13(15) . . . . ?
N1 C8 C9 C14 15.60(19) . . . . ?
C14 C9 C10 C11 0.8(2) . . . . ?
C8 C9 C10 C11 179.42(16) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C12 C13 C14 C15 178.56(19) . . . . ?
C10 C9 C14 C13 -0.8(2) . . . . ?
C8 C9 C14 C13 -179.38(15) . . . . ?
C10 C9 C14 C15 -179.43(15) . . . . ?
C8 C9 C14 C15 1.9(2) . . . . ?
C13 C14 C15 C16 144.85(17) . . . . ?
C9 C14 C15 C16 -36.5(2) . . . . ?
C1 N1 C16 C15 151.52(15) . . . . ?
C8 N1 C16 C15 -37.8(2) . . . . ?
C14 C15 C16 N1 51.5(2) . . . . ?
C8 C7 C17 C18 70.3(2) . . . . ?
C6 C7 C17 C18 -111.31(17) . . . . ?
C8 C7 C17 C22 -109.82(18) . . . . ?
C6 C7 C17 C22 68.6(2) . . . . ?
C22 C17 C18 C19 1.2(2) . . . . ?
C7 C17 C18 C19 -178.89(14) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C23 O1 C20 C19 6.8(2) . . . . ?
C23 O1 C20 C21 -173.85(17) . . . . ?
C18 C19 C20 O1 178.20(15) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
O1 C20 C21 C22 -178.56(16) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C17 0.5(3) . . . . ?
C18 C17 C22 C21 -1.5(2) . . . . ?
C7 C17 C22 C21 178.58(15) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_a60105a
_database_code_depnum_ccdc_archive 'CCDC 1480927'
_audit_update_record             
;
2016-05-19 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40

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                   9.246(4)
_cell_length_b                   21.733(10)
_cell_length_c                   8.690(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.084(6)
_cell_angle_gamma                90
_cell_volume                     1724.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    805
_cell_measurement_theta_min      2.420
_cell_measurement_theta_max      25.936

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8321
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.874
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3697
_reflns_number_gt                2295
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0756P)²] 
 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     SHELXL
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3697
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_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 0.45590(12) 0.28070(5) 0.16903(14) 0.0579(4) Uani 1 1 d . . . . .
N1 N 0.90534(14) 0.19607(6) 0.26259(15) 0.0453(4) Uani 1 1 d . . . . .
C1 C 0.81018(17) 0.15298(7) 0.18988(18) 0.0453(4) Uani 1 1 d . . . . .
C2 C 0.8102(2) 0.08927(8) 0.2036(2) 0.0564(5) Uani 1 1 d . . . . .
H2 H 0.8833 0.0689 0.2703 0.068 Uiso 1 1 calc R U . . .
C3 C 0.6987(2) 0.05754(9) 0.1152(2) 0.0649(5) Uani 1 1 d . . . . .
H3 H 0.6960 0.0149 0.1226 0.078 Uiso 1 1 calc R U . . .
C4 C 0.5900(2) 0.08757(9) 0.0153(2) 0.0626(5) Uani 1 1 d . . . . .
H4 H 0.5162 0.0647 -0.0437 0.075 Uiso 1 1 calc R U . . .
C5 C 0.58910(18) 0.15039(8) 0.00169(19) 0.0538(4) Uani 1 1 d . . . . .
H5 H 0.5154 0.1701 -0.0658 0.065 Uiso 1 1 calc R U . . .
C6 C 0.70002(17) 0.18434(8) 0.09026(17) 0.0444(4) Uani 1 1 d . . . . .
C7 C 0.73148(17) 0.24861(7) 0.10597(18) 0.0421(4) Uani 1 1 d . . . . .
C8 C 0.85559(16) 0.25431(7) 0.21625(17) 0.0409(4) Uani 1 1 d . . . . .
C9 C 0.93718(17) 0.30723(7) 0.29069(17) 0.0436(4) Uani 1 1 d . . . . .
C10 C 0.87783(19) 0.36636(7) 0.29044(19) 0.0517(4) Uani 1 1 d . . . . .
H10 H 0.7838 0.3737 0.2378 0.062 Uiso 1 1 calc R U . . .
C11 C 0.9566(2) 0.41371(8) 0.3668(2) 0.0621(5) Uani 1 1 d . . . . .
H11 H 0.9170 0.4531 0.3626 0.075 Uiso 1 1 calc R U . . .
C12 C 1.0940(2) 0.40333(9) 0.4496(2) 0.0676(6) Uani 1 1 d . . . . .
H12 H 1.1462 0.4354 0.5033 0.081 Uiso 1 1 calc R U . . .
C13 C 1.1534(2) 0.34562(10) 0.4525(2) 0.0627(5) Uani 1 1 d . . . . .
H13 H 1.2462 0.3388 0.5088 0.075 Uiso 1 1 calc R U . . .
C14 C 1.07803(18) 0.29716(8) 0.37333(19) 0.0503(4) Uani 1 1 d . . . . .
C15 C 1.14441(19) 0.23448(9) 0.3704(2) 0.0617(5) Uani 1 1 d . . . . .
H15A H 1.2231 0.2304 0.4579 0.074 Uiso 1 1 calc R U . . .
H15B H 1.1861 0.2298 0.2755 0.074 Uiso 1 1 calc R U . . .
C16 C 1.03371(18) 0.18429(8) 0.3786(2) 0.0543(5) Uani 1 1 d . . . . .
H16A H 1.0757 0.1447 0.3590 0.065 Uiso 1 1 calc R U . . .
H16B H 1.0061 0.1833 0.4818 0.065 Uiso 1 1 calc R U . . .
C17 C 0.64205(17) 0.29757(7) 0.01471(18) 0.0457(4) Uani 1 1 d . . . . .
H17A H 0.6159 0.2838 -0.0922 0.055 Uiso 1 1 calc R U . . .
H17B H 0.7016 0.3343 0.0139 0.055 Uiso 1 1 calc R U . . .
C18 C 0.50431(16) 0.31398(7) 0.07713(17) 0.0424(4) Uani 1 1 d . . . . .
C19 C 0.42495(17) 0.37188(7) 0.02316(18) 0.0454(4) Uani 1 1 d . . . . .
C20 C 0.31795(19) 0.39355(8) 0.1045(2) 0.0557(5) Uani 1 1 d . . . . .
H20 H 0.2978 0.3720 0.1911 0.067 Uiso 1 1 calc R U . . .
C21 C 0.2417(2) 0.44605(9) 0.0597(3) 0.0697(6) Uani 1 1 d . . . . .
H21 H 0.1709 0.4603 0.1160 0.084 Uiso 1 1 calc R U . . .
C22 C 0.2703(3) 0.47763(10) -0.0688(3) 0.0802(7) Uani 1 1 d . . . . .
H22 H 0.2191 0.5136 -0.0989 0.096 Uiso 1 1 calc R U . . .
C23 C 0.3736(3) 0.45656(10) -0.1532(3) 0.0827(7) Uani 1 1 d . . . . .
H23 H 0.3910 0.4779 -0.2411 0.099 Uiso 1 1 calc R U . . .
C24 C 0.4519(2) 0.40370(9) -0.1080(2) 0.0645(5) Uani 1 1 d . . . . .
H24 H 0.5222 0.3895 -0.1651 0.077 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 C18 1.2141(18) . ?
N1 C1 1.369(2) . ?
N1 C8 1.385(2) . ?
N1 C16 1.454(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.405(2) . ?
C2 C3 1.371(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.370(3) . ?
C5 C6 1.393(2) . ?
C6 C7 1.429(2) . ?
C7 C8 1.380(2) . ?
C7 C17 1.496(2) . ?
C8 C9 1.468(2) . ?
C9 C10 1.397(2) . ?
C9 C14 1.401(2) . ?
C10 C11 1.370(2) . ?
C11 C12 1.376(3) . ?
C12 C13 1.368(3) . ?
C13 C14 1.384(2) . ?
C14 C15 1.496(3) . ?
C15 C16 1.505(3) . ?
C17 C18 1.504(2) . ?
C18 C19 1.494(2) . ?
C19 C20 1.386(2) . ?
C19 C24 1.389(2) . ?
C20 C21 1.365(3) . ?
C21 C22 1.371(3) . ?
C22 C23 1.372(3) . ?
C23 C24 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 109.34(13) . . ?
C1 N1 C16 126.48(13) . . ?
C8 N1 C16 124.06(13) . . ?
N1 C1 C2 130.57(16) . . ?
N1 C1 C6 107.65(14) . . ?
C2 C1 C6 121.78(16) . . ?
C3 C2 C1 117.59(17) . . ?
C2 C3 C4 121.47(18) . . ?
C5 C4 C3 121.19(17) . . ?
C4 C5 C6 119.10(17) . . ?
C5 C6 C1 118.86(16) . . ?
C5 C6 C7 133.77(16) . . ?
C1 C6 C7 107.37(14) . . ?
C8 C7 C6 106.77(13) . . ?
C8 C7 C17 129.35(15) . . ?
C6 C7 C17 123.88(14) . . ?
C7 C8 N1 108.77(13) . . ?
C7 C8 C9 133.58(14) . . ?
N1 C8 C9 117.64(14) . . ?
C10 C9 C14 118.51(15) . . ?
C10 C9 C8 123.05(15) . . ?
C14 C9 C8 118.34(14) . . ?
C11 C10 C9 120.76(17) . . ?
C10 C11 C12 120.42(18) . . ?
C13 C12 C11 119.64(18) . . ?
C12 C13 C14 121.30(18) . . ?
C13 C14 C9 119.33(16) . . ?
C13 C14 C15 121.70(16) . . ?
C9 C14 C15 118.95(15) . . ?
C14 C15 C16 112.04(15) . . ?
N1 C16 C15 109.06(14) . . ?
C7 C17 C18 113.97(13) . . ?
O1 C18 C19 119.62(14) . . ?
O1 C18 C17 121.14(14) . . ?
C19 C18 C17 119.24(13) . . ?
C20 C19 C24 118.97(16) . . ?
C20 C19 C18 118.74(15) . . ?
C24 C19 C18 122.27(15) . . ?
C21 C20 C19 121.10(18) . . ?
C20 C21 C22 119.6(2) . . ?
C21 C22 C23 120.5(2) . . ?
C22 C23 C24 120.2(2) . . ?
C23 C24 C19 119.55(19) . . ?

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
C8 N1 C1 C2 -177.14(16) . . . . ?
C16 N1 C1 C2 -1.0(3) . . . . ?
C8 N1 C1 C6 2.24(17) . . . . ?
C16 N1 C1 C6 178.34(14) . . . . ?
N1 C1 C2 C3 179.69(17) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C4 C5 C6 C7 -179.29(17) . . . . ?
N1 C1 C6 C5 179.76(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
N1 C1 C6 C7 -0.36(17) . . . . ?
C2 C1 C6 C7 179.09(14) . . . . ?
C5 C6 C7 C8 178.23(17) . . . . ?
C1 C6 C7 C8 -1.63(17) . . . . ?
C5 C6 C7 C17 -2.2(3) . . . . ?
C1 C6 C7 C17 177.89(14) . . . . ?
C6 C7 C8 N1 3.01(17) . . . . ?
C17 C7 C8 N1 -176.48(15) . . . . ?
C6 C7 C8 C9 -175.57(16) . . . . ?
C17 C7 C8 C9 4.9(3) . . . . ?
C1 N1 C8 C7 -3.33(17) . . . . ?
C16 N1 C8 C7 -179.54(14) . . . . ?
C1 N1 C8 C9 175.51(13) . . . . ?
C16 N1 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C10 17.8(3) . . . . ?
N1 C8 C9 C10 -160.64(14) . . . . ?
C7 C8 C9 C14 -165.91(16) . . . . ?
N1 C8 C9 C14 15.6(2) . . . . ?
C14 C9 C10 C11 1.2(2) . . . . ?
C8 C9 C10 C11 177.46(15) . . . . ?
C9 C10 C11 C12 -2.2(3) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C9 -1.1(3) . . . . ?
C12 C13 C14 C15 177.47(17) . . . . ?
C10 C9 C14 C13 0.4(2) . . . . ?
C8 C9 C14 C13 -176.01(15) . . . . ?
C10 C9 C14 C15 -178.19(15) . . . . ?
C8 C9 C14 C15 5.4(2) . . . . ?
C13 C14 C15 C16 142.20(17) . . . . ?
C9 C14 C15 C16 -39.2(2) . . . . ?
C1 N1 C16 C15 152.14(16) . . . . ?
C8 N1 C16 C15 -32.3(2) . . . . ?
C14 C15 C16 N1 50.0(2) . . . . ?
C8 C7 C17 C18 -100.56(19) . . . . ?
C6 C7 C17 C18 80.03(19) . . . . ?
C7 C17 C18 O1 -15.9(2) . . . . ?
C7 C17 C18 C19 164.90(13) . . . . ?
O1 C18 C19 C20 14.6(2) . . . . ?
C17 C18 C19 C20 -166.19(15) . . . . ?
O1 C18 C19 C24 -163.57(17) . . . . ?
C17 C18 C19 C24 15.6(2) . . . . ?
C24 C19 C20 C21 -1.4(3) . . . . ?
C18 C19 C20 C21 -179.69(16) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C24 -1.1(3) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?
C20 C19 C24 C23 1.0(3) . . . . ?
C18 C19 C24 C23 179.18(17) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2

