# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_mo_51228a
_database_code_depnum_ccdc_archive 'CCDC 1477486'
_audit_update_record             
;
2016-04-30 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47

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                   9.1828(17)
_cell_length_b                   9.0675(17)
_cell_length_c                   26.107(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.376(3)
_cell_angle_gamma                90
_cell_volume                     2173.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7272
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.77

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13774
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         26.806
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4624
_reflns_number_gt                3499
_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-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)+(0.0705P)²+1.1179P] 
 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         4624
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1575
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.004
_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 0.17308(17) 0.2168(2) 0.05409(6) 0.0421(4) Uani 1 1 d . . . . .
N2 N 0.09386(19) 0.3755(2) 0.11792(7) 0.0492(5) Uani 1 1 d . . . . .
O1 O 0.30773(14) 0.30459(17) 0.05548(5) 0.0442(4) Uani 1 1 d . . . . .
O2 O 0.1254(2) 0.6195(2) 0.10673(8) 0.0783(6) Uani 1 1 d . . . . .
O3 O -0.00592(15) 0.39916(18) 0.15660(5) 0.0501(4) Uani 1 1 d . . . . .
C1 C 0.1189(2) 0.2208(2) 0.10634(7) 0.0441(5) Uani 1 1 d . . . . .
H1 H 0.0238 0.1716 0.1057 0.053 Uiso 1 1 calc R U . . .
C2 C 0.2142(2) 0.1415(2) 0.14506(7) 0.0431(5) Uani 1 1 d . . . . .
C3 C 0.2464(2) 0.1908(3) 0.19416(8) 0.0502(5) Uani 1 1 d . . . . .
H3 H 0.2126 0.2821 0.2049 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3296(3) 0.1033(3) 0.22741(8) 0.0566(6) Uani 1 1 d . . . . .
H4 H 0.3506 0.1359 0.2605 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3809(3) -0.0318(3) 0.21142(9) 0.0610(6) Uani 1 1 d . . . . .
H5 H 0.4370 -0.0898 0.2337 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3489(3) -0.0805(3) 0.16224(9) 0.0605(6) Uani 1 1 d . . . . .
H6 H 0.3823 -0.1722 0.1518 0.073 Uiso 1 1 calc R U . . .
C7 C 0.2677(3) 0.0054(3) 0.12834(8) 0.0499(5) Uani 1 1 d . . . . .
C8 C 0.2487(3) -0.0311(3) 0.07442(9) 0.0562(6) Uani 1 1 d . . . . .
H8 H 0.2591 -0.1288 0.0642 0.067 Uiso 1 1 calc R U . . .
C9 C 0.2166(2) 0.0710(3) 0.03885(8) 0.0469(5) Uani 1 1 d . . . . .
C10 C 0.2266(2) 0.0496(3) -0.01729(8) 0.0481(5) Uani 1 1 d . . . . .
C11 C 0.1371(3) 0.1271(3) -0.05106(8) 0.0548(6) Uani 1 1 d . . . . .
H11 H 0.0685 0.1922 -0.0384 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1482(3) 0.1092(3) -0.10369(9) 0.0621(7) Uani 1 1 d . . . . .
H12 H 0.0869 0.1612 -0.1261 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2507(3) 0.0138(3) -0.12247(9) 0.0669(7) Uani 1 1 d . . . . .
H13 H 0.2593 0.0024 -0.1577 0.080 Uiso 1 1 calc R U . . .
C14 C 0.3402(3) -0.0647(3) -0.08957(10) 0.0681(7) Uani 1 1 d . . . . .
H14 H 0.4085 -0.1298 -0.1024 0.082 Uiso 1 1 calc R U . . .
C15 C 0.3284(3) -0.0464(3) -0.03711(9) 0.0578(6) Uani 1 1 d . . . . .
H15 H 0.3896 -0.0992 -0.0149 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2697(2) 0.4582(3) 0.05557(8) 0.0459(5) Uani 1 1 d . . . . .
C17 C 0.1568(2) 0.4925(3) 0.09625(8) 0.0492(5) Uani 1 1 d . . . . .
C18 C -0.1474(2) 0.4341(3) 0.13412(8) 0.0544(6) Uani 1 1 d . . . . .
H18A H -0.1756 0.3598 0.1091 0.065 Uiso 1 1 calc R U . . .
H18B H -0.1443 0.5290 0.1171 0.065 Uiso 1 1 calc R U . . .
C19 C -0.2549(2) 0.4380(2) 0.17651(7) 0.0419(5) Uani 1 1 d . . . . .
C20 C -0.2644(2) 0.3228(3) 0.21080(9) 0.0521(6) Uani 1 1 d . . . . .
H20 H -0.2007 0.2434 0.2085 0.063 Uiso 1 1 calc R U . . .
C21 C -0.3677(3) 0.3239(3) 0.24862(9) 0.0583(6) Uani 1 1 d . . . . .
H21 H -0.3722 0.2463 0.2718 0.070 Uiso 1 1 calc R U . . .
C22 C -0.4630(2) 0.4391(3) 0.25180(9) 0.0577(6) Uani 1 1 d . . . . .
H22 H -0.5333 0.4393 0.2769 0.069 Uiso 1 1 calc R U . . .
C23 C -0.4550(3) 0.5539(3) 0.21803(9) 0.0563(6) Uani 1 1 d . . . . .
H23 H -0.5203 0.6319 0.2201 0.068 Uiso 1 1 calc R U . . .
C24 C -0.3500(2) 0.5547(3) 0.18084(8) 0.0497(5) Uani 1 1 d . . . . .
H24 H -0.3435 0.6346 0.1586 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2111(3) 0.5075(3) 0.00338(9) 0.0587(6) Uani 1 1 d . . . . .
H25A H 0.2812 0.4853 -0.0222 0.088 Uiso 1 1 calc R U . . .
H25B H 0.1934 0.6118 0.0039 0.088 Uiso 1 1 calc R U . . .
H25C H 0.1218 0.4564 -0.0045 0.088 Uiso 1 1 calc R U . . .
C26 C 0.4115(3) 0.5344(3) 0.07061(11) 0.0664(7) Uani 1 1 d . . . . .
H26A H 0.4446 0.4996 0.1036 0.100 Uiso 1 1 calc R U . . .
H26B H 0.3961 0.6390 0.0721 0.100 Uiso 1 1 calc R U . . .
H26C H 0.4837 0.5128 0.0457 0.100 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 C9 1.440(3) . ?
N1 C1 1.463(2) . ?
N1 O1 1.470(2) . ?
N2 C17 1.340(3) . ?
N2 O3 1.396(2) . ?
N2 C1 1.455(3) . ?
O1 C16 1.436(3) . ?
O2 C17 1.220(3) . ?
O3 C18 1.447(3) . ?
C1 C2 1.504(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.381(4) . ?
C5 C6 1.383(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.453(3) . ?
C8 C9 1.339(3) . ?
C9 C10 1.484(3) . ?
C10 C11 1.382(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.377(4) . ?
C13 C14 1.374(4) . ?
C14 C15 1.386(3) . ?
C16 C26 1.518(3) . ?
C16 C25 1.520(3) . ?
C16 C17 1.534(3) . ?
C18 C19 1.501(3) . ?
C19 C24 1.378(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.386(3) . ?
C21 C22 1.367(3) . ?
C22 C23 1.368(4) . ?
C23 C24 1.385(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
C9 N1 C1 112.52(17) . . ?
C9 N1 O1 105.36(14) . . ?
C1 N1 O1 105.57(14) . . ?
C17 N2 O3 118.74(17) . . ?
C17 N2 C1 127.16(17) . . ?
O3 N2 C1 114.10(16) . . ?
C16 O1 N1 108.71(14) . . ?
N2 O3 C18 109.78(15) . . ?
N2 C1 N1 106.05(17) . . ?
N2 C1 C2 114.42(17) . . ?
N1 C1 C2 114.17(16) . . ?
C3 C2 C7 120.3(2) . . ?
C3 C2 C1 125.2(2) . . ?
C7 C2 C1 114.47(18) . . ?
C2 C3 C4 119.8(2) . . ?
C5 C4 C3 120.2(2) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C6 C7 120.9(2) . . ?
C6 C7 C2 119.0(2) . . ?
C6 C7 C8 122.8(2) . . ?
C2 C7 C8 117.9(2) . . ?
C9 C8 C7 122.3(2) . . ?
C8 C9 N1 120.07(19) . . ?
C8 C9 C10 125.3(2) . . ?
N1 C9 C10 114.64(19) . . ?
C11 C10 C15 118.5(2) . . ?
C11 C10 C9 120.9(2) . . ?
C15 C10 C9 120.6(2) . . ?
C10 C11 C12 120.9(2) . . ?
C13 C12 C11 119.5(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 119.7(2) . . ?
C14 C15 C10 120.9(2) . . ?
O1 C16 C26 103.58(18) . . ?
O1 C16 C25 111.38(19) . . ?
C26 C16 C25 112.4(2) . . ?
O1 C16 C17 111.51(18) . . ?
C26 C16 C17 108.56(19) . . ?
C25 C16 C17 109.29(18) . . ?
O2 C17 N2 123.1(2) . . ?
O2 C17 C16 121.0(2) . . ?
N2 C17 C16 115.91(19) . . ?
O3 C18 C19 107.84(16) . . ?
C24 C19 C20 118.60(19) . . ?
C24 C19 C18 120.5(2) . . ?
C20 C19 C18 120.8(2) . . ?
C19 C20 C21 120.8(2) . . ?
C22 C21 C20 119.9(2) . . ?
C21 C22 C23 119.9(2) . . ?
C22 C23 C24 120.4(2) . . ?
C19 C24 C23 120.4(2) . . ?

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
C9 N1 O1 C16 163.38(15) . . . . ?
C1 N1 O1 C16 -77.36(18) . . . . ?
C17 N2 O3 C18 82.0(2) . . . . ?
C1 N2 O3 C18 -98.9(2) . . . . ?
C17 N2 C1 N1 -23.8(3) . . . . ?
O3 N2 C1 N1 157.18(15) . . . . ?
C17 N2 C1 C2 103.0(2) . . . . ?
O3 N2 C1 C2 -76.1(2) . . . . ?
C9 N1 C1 N2 174.29(16) . . . . ?
O1 N1 C1 N2 59.89(19) . . . . ?
C9 N1 C1 C2 47.4(2) . . . . ?
O1 N1 C1 C2 -67.0(2) . . . . ?
N2 C1 C2 C3 16.9(3) . . . . ?
N1 C1 C2 C3 139.4(2) . . . . ?
N2 C1 C2 C7 -165.08(18) . . . . ?
N1 C1 C2 C7 -42.6(3) . . . . ?
C7 C2 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 C4 176.4(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C5 C6 C7 C2 -1.9(4) . . . . ?
C5 C6 C7 C8 171.0(2) . . . . ?
C3 C2 C7 C6 2.1(3) . . . . ?
C1 C2 C7 C6 -176.0(2) . . . . ?
C3 C2 C7 C8 -171.2(2) . . . . ?
C1 C2 C7 C8 10.7(3) . . . . ?
C6 C7 C8 C9 -156.1(3) . . . . ?
C2 C7 C8 C9 17.0(4) . . . . ?
C7 C8 C9 N1 -11.7(4) . . . . ?
C7 C8 C9 C10 166.1(2) . . . . ?
C1 N1 C9 C8 -20.8(3) . . . . ?
O1 N1 C9 C8 93.7(2) . . . . ?
C1 N1 C9 C10 161.19(18) . . . . ?
O1 N1 C9 C10 -84.3(2) . . . . ?
C8 C9 C10 C11 151.3(3) . . . . ?
N1 C9 C10 C11 -30.9(3) . . . . ?
C8 C9 C10 C15 -30.1(4) . . . . ?
N1 C9 C10 C15 147.7(2) . . . . ?
C15 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 C12 178.8(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
C11 C10 C15 C14 -0.1(4) . . . . ?
C9 C10 C15 C14 -178.7(2) . . . . ?
N1 O1 C16 C26 166.04(16) . . . . ?
N1 O1 C16 C25 -72.92(19) . . . . ?
N1 O1 C16 C17 49.5(2) . . . . ?
O3 N2 C17 O2 -4.1(3) . . . . ?
C1 N2 C17 O2 177.0(2) . . . . ?
O3 N2 C17 C16 177.65(17) . . . . ?
C1 N2 C17 C16 -1.3(3) . . . . ?
O1 C16 C17 O2 170.3(2) . . . . ?
C26 C16 C17 O2 56.8(3) . . . . ?
C25 C16 C17 O2 -66.2(3) . . . . ?
O1 C16 C17 N2 -11.4(3) . . . . ?
C26 C16 C17 N2 -124.9(2) . . . . ?
C25 C16 C17 N2 112.1(2) . . . . ?
N2 O3 C18 C19 172.38(18) . . . . ?
O3 C18 C19 C24 131.5(2) . . . . ?
O3 C18 C19 C20 -50.9(3) . . . . ?
C24 C19 C20 C21 0.3(3) . . . . ?
C18 C19 C20 C21 -177.4(2) . . . . ?
C19 C20 C21 C22 0.9(4) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C20 C19 C24 C23 -1.7(3) . . . . ?
C18 C19 C24 C23 176.0(2) . . . . ?
C22 C23 C24 C19 1.8(4) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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 
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data_mo_51229a
_database_code_depnum_ccdc_archive 'CCDC 1477487'
_audit_update_record             
;
2016-04-30 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   38.327(12)
_cell_length_b                   12.158(4)
_cell_length_c                   9.715(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.510(6)
_cell_angle_gamma                90
_cell_volume                     4506(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2695
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      23.05

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            15292
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         26.768
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4784
_reflns_number_gt                2529
_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-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)+(0.0957P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4784
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1817
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.34734(5) 0.74490(14) 0.04627(17) 0.0515(4) Uani 1 1 d . . . . .
N2 N 0.34148(6) 0.48840(16) 0.0357(2) 0.0676(6) Uani 1 1 d . . . . .
O1 O 0.29786(4) 0.65322(11) 0.09966(14) 0.0559(4) Uani 1 1 d . . . . .
O2 O 0.33419(5) 0.53407(16) -0.18762(16) 0.0871(6) Uani 1 1 d . . . . .
O3 O 0.37028(5) 0.42271(13) 0.01697(18) 0.0746(5) Uani 1 1 d . . . . .
C1 C 0.32425(5) 0.72590(15) 0.1326(2) 0.0486(5) Uani 1 1 d . . . . .
C2 C 0.32379(5) 0.77576(16) 0.2655(2) 0.0481(5) Uani 1 1 d . . . . .
C3 C 0.29931(6) 0.75083(18) 0.3590(2) 0.0570(6) Uani 1 1 d . . . . .
H3 H 0.2818 0.6993 0.3353 0.068 Uiso 1 1 calc R U . . .
C4 C 0.30091(7) 0.8015(2) 0.4841(2) 0.0694(7) Uani 1 1 d . . . . .
H4 H 0.2845 0.7847 0.5457 0.083 Uiso 1 1 calc R U . . .
C5 C 0.32714(8) 0.8788(2) 0.5201(3) 0.0832(8) Uani 1 1 d . . . . .
H5 H 0.3281 0.9135 0.6057 0.100 Uiso 1 1 calc R U . . .
C6 C 0.35110(7) 0.9036(2) 0.4324(3) 0.0815(8) Uani 1 1 d . . . . .
H6 H 0.3684 0.9552 0.4583 0.098 Uiso 1 1 calc R U . . .
C7 C 0.35035(6) 0.85239(17) 0.3012(2) 0.0580(6) Uani 1 1 d . . . . .
C8 C 0.37500(6) 0.87413(19) 0.2053(3) 0.0646(6) Uani 1 1 d . . . . .
H8 H 0.3925 0.9262 0.2265 0.078 Uiso 1 1 calc R U . . .
C9 C 0.37345(6) 0.81961(16) 0.0820(2) 0.0545(5) Uani 1 1 d . . . . .
C10 C 0.29338(6) 0.60623(19) -0.0392(2) 0.0613(6) Uani 1 1 d . . . . .
C11 C 0.32543(6) 0.54107(18) -0.0702(2) 0.0590(6) Uani 1 1 d . . . . .
C12 C 0.40129(7) 0.4883(2) 0.0265(3) 0.0911(9) Uani 1 1 d . . . . .
H12A H 0.4058 0.5183 0.1190 0.109 Uiso 1 1 calc R U . . .
H12B H 0.3986 0.5489 -0.0385 0.109 Uiso 1 1 calc R U . . .
C13 C 0.43074(7) 0.4166(2) -0.0060(3) 0.0730(7) Uani 1 1 d . . . . .
C14 C 0.42705(8) 0.3454(3) -0.1159(3) 0.0898(8) Uani 1 1 d . . . . .
H14 H 0.4059 0.3425 -0.1715 0.108 Uiso 1 1 calc R U . . .
C15 C 0.45401(11) 0.2790(3) -0.1444(4) 0.1248(13) Uani 1 1 d . . . . .
H15 H 0.4511 0.2309 -0.2191 0.150 Uiso 1 1 calc R U . . .
C16 C 0.48499(11) 0.2823(4) -0.0651(5) 0.1252(14) Uani 1 1 d . . . . .
H16 H 0.5033 0.2370 -0.0861 0.150 Uiso 1 1 calc R U . . .
C17 C 0.48951(9) 0.3509(4) 0.0445(4) 0.1165(12) Uani 1 1 d . . . . .
H17 H 0.5108 0.3529 0.0991 0.140 Uiso 1 1 calc R U . . .
C18 C 0.46230(9) 0.4180(3) 0.0746(4) 0.1004(10) Uani 1 1 d . . . . .
H18 H 0.4653 0.4648 0.1505 0.121 Uiso 1 1 calc R U . . .
C19 C 0.26249(7) 0.5278(2) -0.0310(3) 0.0850(8) Uani 1 1 d . . . . .
H19A H 0.2682 0.4745 0.0405 0.127 Uiso 1 1 calc R U . . .
H19B H 0.2576 0.4908 -0.1181 0.127 Uiso 1 1 calc R U . . .
H19C H 0.2422 0.5688 -0.0104 0.127 Uiso 1 1 calc R U . . .
C20 C 0.28417(7) 0.6949(2) -0.1475(3) 0.0863(8) Uani 1 1 d . . . . .
H20A H 0.2656 0.7398 -0.1191 0.129 Uiso 1 1 calc R U . . .
H20B H 0.2768 0.6609 -0.2346 0.129 Uiso 1 1 calc R U . . .
H20C H 0.3044 0.7398 -0.1570 0.129 Uiso 1 1 calc R U . . .
C21 C 0.39851(6) 0.83642(18) -0.0224(2) 0.0578(6) Uani 1 1 d . . . . .
C22 C 0.39316(7) 0.7860(2) -0.1517(3) 0.0743(7) Uani 1 1 d . . . . .
H22 H 0.3738 0.7406 -0.1714 0.089 Uiso 1 1 calc R U . . .
C23 C 0.41604(9) 0.8023(2) -0.2509(3) 0.0887(9) Uani 1 1 d . . . . .
H23 H 0.4119 0.7679 -0.3364 0.106 Uiso 1 1 calc R U . . .
C24 C 0.44473(8) 0.8685(3) -0.2247(4) 0.0894(9) Uani 1 1 d . . . . .
H24 H 0.4602 0.8790 -0.2916 0.107 Uiso 1 1 calc R U . . .
C25 C 0.45040(7) 0.9193(3) -0.0989(4) 0.0905(9) Uani 1 1 d . . . . .
H25 H 0.4698 0.9648 -0.0805 0.109 Uiso 1 1 calc R U . . .
C26 C 0.42764(7) 0.9036(2) 0.0008(3) 0.0776(7) Uani 1 1 d . . . . .
H26 H 0.4319 0.9389 0.0856 0.093 Uiso 1 1 calc R U . . .
H2 H 0.3348(6) 0.489(2) 0.117(3) 0.070(8) 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
N1 C1 1.297(3) . ?
N1 C9 1.371(3) . ?
N2 C11 1.314(3) . ?
N2 O3 1.388(2) . ?
N2 H2 0.85(2) . ?
O1 C1 1.358(2) . ?
O1 C10 1.460(2) . ?
O2 C11 1.222(3) . ?
O3 C12 1.427(3) . ?
C1 C2 1.428(3) . ?
C2 C7 1.399(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.358(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.346(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.414(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9300 . ?
C9 C21 1.477(3) . ?
C10 C11 1.516(3) . ?
C10 C20 1.524(3) . ?
C10 C19 1.528(3) . ?
C12 C13 1.484(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.371(4) . ?
C13 C18 1.377(4) . ?
C14 C15 1.361(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.353(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.350(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.384(3) . ?
C21 C22 1.395(3) . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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 C9 118.73(18) . . ?
C11 N2 O3 119.7(2) . . ?
C11 N2 H2 124.0(17) . . ?
O3 N2 H2 116.2(17) . . ?
C1 O1 C10 119.43(16) . . ?
N2 O3 C12 109.74(18) . . ?
N1 C1 O1 120.15(18) . . ?
N1 C1 C2 125.28(19) . . ?
O1 C1 C2 114.57(19) . . ?
C7 C2 C3 120.1(2) . . ?
C7 C2 C1 115.8(2) . . ?
C3 C2 C1 124.19(19) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C8 118.6(2) . . ?
C2 C7 C6 117.8(2) . . ?
C8 C7 C6 123.6(2) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 N1 120.9(2) . . ?
C8 C9 C21 124.0(2) . . ?
N1 C9 C21 115.11(19) . . ?
O1 C10 C11 111.24(17) . . ?
O1 C10 C20 111.10(19) . . ?
C11 C10 C20 111.8(2) . . ?
O1 C10 C19 102.65(18) . . ?
C11 C10 C19 109.32(19) . . ?
C20 C10 C19 110.4(2) . . ?
O2 C11 N2 123.2(2) . . ?
O2 C11 C10 121.5(2) . . ?
N2 C11 C10 115.2(2) . . ?
O3 C12 C13 107.7(2) . . ?
O3 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O3 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 C18 118.1(3) . . ?
C14 C13 C12 120.8(3) . . ?
C18 C13 C12 121.1(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.4(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 120.9(3) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 116.9(2) . . ?
C26 C21 C9 122.5(2) . . ?
C22 C21 C9 120.6(2) . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.2(3) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 120.6(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 121.5(3) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?

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
C11 N2 O3 C12 85.5(3) . . . . ?
C9 N1 C1 O1 179.33(17) . . . . ?
C9 N1 C1 C2 -0.9(3) . . . . ?
C10 O1 C1 N1 -6.9(3) . . . . ?
C10 O1 C1 C2 173.33(16) . . . . ?
N1 C1 C2 C7 1.3(3) . . . . ?
O1 C1 C2 C7 -178.96(17) . . . . ?
N1 C1 C2 C3 -177.54(19) . . . . ?
O1 C1 C2 C3 2.2(3) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 179.4(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C3 C2 C7 C8 178.88(19) . . . . ?
C1 C2 C7 C8 0.0(3) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C1 C2 C7 C6 -179.6(2) . . . . ?
C5 C6 C7 C2 0.4(4) . . . . ?
C5 C6 C7 C8 -179.3(3) . . . . ?
C2 C7 C8 C9 -1.6(3) . . . . ?
C6 C7 C8 C9 178.1(2) . . . . ?
C7 C8 C9 N1 2.0(3) . . . . ?
C7 C8 C9 C21 -179.0(2) . . . . ?
C1 N1 C9 C8 -0.8(3) . . . . ?
C1 N1 C9 C21 -179.82(17) . . . . ?
C1 O1 C10 C11 61.2(2) . . . . ?
C1 O1 C10 C20 -64.0(2) . . . . ?
C1 O1 C10 C19 178.06(18) . . . . ?
O3 N2 C11 O2 1.3(3) . . . . ?
O3 N2 C11 C10 177.39(18) . . . . ?
O1 C10 C11 O2 -149.0(2) . . . . ?
C20 C10 C11 O2 -24.2(3) . . . . ?
C19 C10 C11 O2 98.3(2) . . . . ?
O1 C10 C11 N2 34.8(3) . . . . ?
C20 C10 C11 N2 159.6(2) . . . . ?
C19 C10 C11 N2 -77.9(2) . . . . ?
N2 O3 C12 C13 -175.2(2) . . . . ?
O3 C12 C13 C14 44.6(4) . . . . ?
O3 C12 C13 C18 -134.1(3) . . . . ?
C18 C13 C14 C15 -0.5(5) . . . . ?
C12 C13 C14 C15 -179.3(3) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.6(7) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C14 C13 C18 C17 0.9(5) . . . . ?
C12 C13 C18 C17 179.7(3) . . . . ?
C16 C17 C18 C13 -0.6(5) . . . . ?
C8 C9 C21 C26 5.2(3) . . . . ?
N1 C9 C21 C26 -175.8(2) . . . . ?
C8 C9 C21 C22 -173.4(2) . . . . ?
N1 C9 C21 C22 5.6(3) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
C9 C21 C22 C23 179.0(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C24 C25 C26 C21 0.1(4) . . . . ?
C22 C21 C26 C25 -0.4(4) . . . . ?
C9 C21 C26 C25 -179.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.85(2) 1.92(3) 2.743(3) 161(2) 6_566

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-2

