# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_cs-sr-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N O4'
_chemical_formula_weight         399.43

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4396(6)
_cell_length_b                   10.7479(7)
_cell_length_c                   11.8458(7)
_cell_angle_alpha                104.955(6)
_cell_angle_beta                 96.292(5)
_cell_angle_gamma                96.603(5)
_cell_volume                     1020.31(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11252
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         29.15
_reflns_number_total             4730
_reflns_number_gt                2673
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0555P)²+0.0049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4730
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.46678(15) 0.08686(13) -0.10581(11) 0.0493(4) Uani 1 1 d . . .
O2 O 0.38335(17) 0.47064(13) 0.25616(12) 0.0570(4) Uani 1 1 d . . .
O3 O 0.24505(17) 0.42435(14) -0.28752(12) 0.0604(4) Uani 1 1 d . . .
O4 O 0.18384(18) 0.60302(14) -0.11553(13) 0.0635(4) Uani 1 1 d . . .
N1 N 0.45145(16) 0.16127(14) 0.08775(12) 0.0384(4) Uani 1 1 d . . .
H1 H 0.5057 0.1021 0.1007 0.046 Uiso 1 1 calc R . .
C1 C 0.39308(19) 0.24277(17) 0.19002(15) 0.0348(4) Uani 1 1 d . . .
C2 C 0.37311(19) 0.37607(18) 0.17123(16) 0.0379(4) Uani 1 1 d . . .
C3 C 0.33381(19) 0.38368(17) 0.04959(15) 0.0348(4) Uani 1 1 d . . .
C4 C 0.2748(2) 0.49314(18) 0.02833(17) 0.0409(5) Uani 1 1 d . . .
H4 H 0.2574 0.5598 0.0914 0.049 Uiso 1 1 calc R . .
C5 C 0.2425(2) 0.50286(18) -0.08461(17) 0.0434(5) Uani 1 1 d . . .
C6 C 0.2754(2) 0.40268(19) -0.18015(17) 0.0430(5) Uani 1 1 d . . .
C7 C 0.3325(2) 0.29534(18) -0.15878(16) 0.0404(5) Uani 1 1 d . . .
H7 H 0.3522 0.2292 -0.2214 0.049 Uiso 1 1 calc R . .
C8 C 0.36109(19) 0.28468(17) -0.04399(15) 0.0346(4) Uani 1 1 d . . .
C9 C 0.42881(19) 0.16981(18) -0.02347(16) 0.0365(4) Uani 1 1 d . . .
C10 C 0.2885(3) 0.3336(3) -0.38567(19) 0.0778(7) Uani 1 1 d . . .
H10A H 0.2610 0.3594 -0.4563 0.117 Uiso 1 1 calc R . .
H10B H 0.2314 0.2485 -0.3938 0.117 Uiso 1 1 calc R . .
H10C H 0.4024 0.3318 -0.3731 0.117 Uiso 1 1 calc R . .
C11 C 0.1421(3) 0.7033(2) -0.0241(2) 0.0640(6) Uani 1 1 d . . .
H11A H 0.1023 0.7684 -0.0573 0.096 Uiso 1 1 calc R . .
H11B H 0.2356 0.7423 0.0333 0.096 Uiso 1 1 calc R . .
H11C H 0.0600 0.6669 0.0131 0.096 Uiso 1 1 calc R . .
C12 C 0.5161(2) 0.25882(19) 0.29782(16) 0.0419(5) Uani 1 1 d . . .
H12 H 0.5908 0.3346 0.3217 0.050 Uiso 1 1 calc R . .
C13 C 0.5259(2) 0.1757(2) 0.35970(18) 0.0517(5) Uani 1 1 d . . .
H13 H 0.4473 0.1025 0.3373 0.062 Uiso 1 1 calc R . .
C14 C 0.6472(2) 0.1846(2) 0.46095(17) 0.0476(5) Uani 1 1 d . . .
C15 C 0.7234(2) 0.3027(2) 0.53400(18) 0.0599(6) Uani 1 1 d . . .
H15 H 0.6959 0.3792 0.5198 0.072 Uiso 1 1 calc R . .
C16 C 0.8410(3) 0.3097(3) 0.6289(2) 0.0751(7) Uani 1 1 d . . .
H16 H 0.8914 0.3901 0.6776 0.090 Uiso 1 1 calc R . .
C17 C 0.8813(3) 0.1971(3) 0.6495(2) 0.0830(8) Uani 1 1 d . . .
H17 H 0.9596 0.2010 0.7125 0.100 Uiso 1 1 calc R . .
C18 C 0.8067(3) 0.0773(3) 0.5773(2) 0.0817(8) Uani 1 1 d . . .
H18 H 0.8349 0.0009 0.5912 0.098 Uiso 1 1 calc R . .
C19 C 0.6906(3) 0.0724(3) 0.4848(2) 0.0677(7) Uani 1 1 d . . .
H19 H 0.6398 -0.0082 0.4369 0.081 Uiso 1 1 calc R . .
C20 C 0.2246(2) 0.18201(18) 0.20525(15) 0.0364(4) Uani 1 1 d . . .
C21 C 0.1394(2) 0.2517(2) 0.28659(17) 0.0545(6) Uani 1 1 d . . .
H21 H 0.1843 0.3352 0.3319 0.065 Uiso 1 1 calc R . .
C22 C -0.0110(3) 0.1994(3) 0.3015(2) 0.0684(7) Uani 1 1 d . . .
H22 H -0.0666 0.2479 0.3566 0.082 Uiso 1 1 calc R . .
C23 C -0.0797(2) 0.0764(3) 0.23579(19) 0.0613(6) Uani 1 1 d . . .
H23 H -0.1816 0.0413 0.2456 0.074 Uiso 1 1 calc R . .
C24 C 0.0038(2) 0.0063(2) 0.15580(19) 0.0562(6) Uani 1 1 d . . .
H24 H -0.0413 -0.0775 0.1115 0.067 Uiso 1 1 calc R . .
C25 C 0.1547(2) 0.05832(19) 0.13978(17) 0.0467(5) Uani 1 1 d . . .
H25 H 0.2095 0.0095 0.0844 0.056 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.239(2) . ?
O2 C2 1.219(2) . ?
O3 C6 1.354(2) . ?
O3 C10 1.424(3) . ?
O4 C5 1.351(2) . ?
O4 C11 1.424(2) . ?
N1 C9 1.339(2) . ?
N1 C1 1.470(2) . ?
N1 H1 0.8600 . ?
C1 C12 1.514(2) . ?
C1 C2 1.531(3) . ?
C1 C20 1.544(2) . ?
C2 C3 1.468(2) . ?
C3 C8 1.385(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(3) . ?
C6 C7 1.371(3) . ?
C7 C8 1.391(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.482(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.297(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.464(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 C19 1.386(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.380(2) . ?
C20 C21 1.382(2) . ?
C21 C22 1.376(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9300 . ?
C25 H25 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
C6 O3 C10 117.40(17) . . ?
C5 O4 C11 117.53(16) . . ?
C9 N1 C1 126.63(15) . . ?
C9 N1 H1 116.7 . . ?
C1 N1 H1 116.7 . . ?
N1 C1 C12 107.81(13) . . ?
N1 C1 C2 110.27(14) . . ?
C12 C1 C2 110.01(15) . . ?
N1 C1 C20 111.05(14) . . ?
C12 C1 C20 111.76(14) . . ?
C2 C1 C20 105.96(13) . . ?
O2 C2 C3 122.08(18) . . ?
O2 C2 C1 119.92(17) . . ?
C3 C2 C1 117.94(15) . . ?
C8 C3 C4 119.93(17) . . ?
C8 C3 C2 119.95(17) . . ?
C4 C3 C2 120.07(16) . . ?
C5 C4 C3 120.48(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
O4 C5 C4 125.57(18) . . ?
O4 C5 C6 115.09(17) . . ?
C4 C5 C6 119.32(18) . . ?
O3 C6 C7 125.62(18) . . ?
O3 C6 C5 114.51(18) . . ?
C7 C6 C5 119.87(18) . . ?
C6 C7 C8 120.40(18) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 119.94(17) . . ?
C3 C8 C9 120.94(16) . . ?
C7 C8 C9 119.03(16) . . ?
O1 C9 N1 121.44(17) . . ?
O1 C9 C8 121.11(16) . . ?
N1 C9 C8 117.43(16) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 125.47(17) . . ?
C13 C12 H12 117.3 . . ?
C1 C12 H12 117.3 . . ?
C12 C13 C14 127.20(19) . . ?
C12 C13 H13 116.4 . . ?
C14 C13 H13 116.4 . . ?
C15 C14 C19 117.9(2) . . ?
C15 C14 C13 121.9(2) . . ?
C19 C14 C13 120.3(2) . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 121.7(2) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C25 C20 C21 118.05(17) . . ?
C25 C20 C1 121.93(16) . . ?
C21 C20 C1 120.02(17) . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 119.0(2) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 120.9(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C20 C25 C24 120.59(19) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.859
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 959881'
