# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_A3_1_a
_database_code_depnum_ccdc_archive 'CCDC 1007420'
_audit_update_record             
;
2014-06-09 deposited with the CCDC.
2015-06-04 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 H21 N O'
_chemical_formula_weight         363.44

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           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                   28.0546(17)
_cell_length_b                   9.6810(5)
_cell_length_c                   15.0716(8)

_cell_angle_alpha                90
_cell_angle_beta                 109.781(6)
_cell_angle_gamma                90
_cell_volume                     3851.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3001
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      24.26

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?

_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.076

_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?


_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            35240
_diffrn_reflns_av_unetI/netI     0.0498

_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         28.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             4832
_reflns_number_gt                2521
_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)+(0.0669P)²+0.0574P] 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         4832
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1161
_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













O001 O 0.26492(5) 0.66675(11) 0.19622(8) 0.0597(4) Uani 1 1 d . . . . .
H001 H 0.2760 0.6190 0.2437 0.090 Uiso 1 1 calc R U . . .
N002 N 0.18751(5) 0.98082(12) 0.13938(9) 0.0448(3) Uani 1 1 d . . . . .
C003 C 0.10742(5) 1.09604(16) 0.11100(11) 0.0438(4) Uani 1 1 d . . . . .
C004 C 0.20861(6) 0.75684(15) 0.27412(12) 0.0441(4) Uani 1 1 d . . . . .
C005 C 0.21523(5) 0.85894(15) 0.12369(11) 0.0443(4) Uani 1 1 d . . . . .
H005 H 0.1909 0.7934 0.0832 0.053 Uiso 1 1 calc R U . . .
C006 C 0.13958(6) 0.97746(16) 0.10589(11) 0.0455(4) Uani 1 1 d . . . . .
H006 H 0.1239 0.8968 0.0768 0.055 Uiso 1 1 calc R U . . .
C007 C 0.05863(5) 1.07743(16) 0.11581(11) 0.0434(4) Uani 1 1 d . . . . .
C008 C 0.02867(6) 1.19605(16) 0.11710(11) 0.0449(4) Uani 1 1 d . . . . .
C009 C 0.04767(6) 1.33082(16) 0.11175(12) 0.0483(4) Uani 1 1 d . . . . .
C00A C -0.02079(6) 1.18092(17) 0.12365(11) 0.0476(4) Uani 1 1 d . . . . .
C00B C 0.12538(6) 1.22933(16) 0.10695(12) 0.0488(4) Uani 1 1 d . . . . .
H00B H 0.1578 1.2412 0.1047 0.059 Uiso 1 1 calc R U . . .
C00C C 0.24286(6) 0.78954(15) 0.21797(12) 0.0466(4) Uani 1 1 d . . . . .
H3 H 0.2701 0.8507 0.2555 0.056 Uiso 1 1 calc R U . . .
C00D C -0.03996(6) 1.04768(18) 0.13046(12) 0.0529(4) Uani 1 1 d . . . . .
C00E C -0.05063(6) 1.30001(19) 0.12370(12) 0.0557(5) Uani 1 1 d . . . . .
C00F C 0.09613(6) 1.34385(17) 0.10621(12) 0.0537(4) Uani 1 1 d . . . . .
H00F H 0.1089 1.4313 0.1020 0.064 Uiso 1 1 calc R U . . .
C00G C 0.03724(6) 0.94385(17) 0.12237(12) 0.0537(4) Uani 1 1 d . . . . .
H00G H 0.0560 0.8649 0.1220 0.064 Uiso 1 1 calc R U . . .
C00H C 0.16827(7) 0.66592(17) 0.23928(13) 0.0585(5) Uani 1 1 d . . . . .
H00H H 0.1622 0.6255 0.1805 0.070 Uiso 1 1 calc R U . . .
C00I C 0.21671(6) 0.81516(16) 0.36158(13) 0.0517(4) Uani 1 1 d . . . . .
H00I H 0.2432 0.8773 0.3860 0.062 Uiso 1 1 calc R U . . .
C00J C 0.25139(6) 0.90451(18) 0.07394(13) 0.0565(5) Uani 1 1 d . . . . .
H00A H 0.2324 0.9340 0.0111 0.085 Uiso 1 1 calc R U . . .
H4 H 0.2729 0.8287 0.0713 0.085 Uiso 1 1 calc R U . . .
H00D H 0.2718 0.9797 0.1080 0.085 Uiso 1 1 calc R U . . .
C00K C -0.00909(6) 0.93051(19) 0.12904(13) 0.0589(5) Uani 1 1 d . . . . .
H00K H -0.0215 0.8424 0.1329 0.071 Uiso 1 1 calc R U . . .
C00L C 0.18596(7) 0.78244(18) 0.41319(13) 0.0600(5) Uani 1 1 d . . . . .
H00L H 0.1921 0.8221 0.4722 0.072 Uiso 1 1 calc R U . . .
C00M C 0.01629(7) 1.44824(18) 0.11188(13) 0.0618(5) Uani 1 1 d . . . . .
H00M H 0.0283 1.5367 0.1077 0.074 Uiso 1 1 calc R U . . .
C00N C 0.14639(7) 0.69168(18) 0.37789(15) 0.0622(5) Uani 1 1 d . . . . .
H00N H 0.1260 0.6691 0.4132 0.075 Uiso 1 1 calc R U . . .
C00O C 0.13715(7) 0.63442(19) 0.29015(15) 0.0641(5) Uani 1 1 d . . . . .
H00O H 0.1100 0.5746 0.2652 0.077 Uiso 1 1 calc R U . . .
C00P C -0.02987(7) 1.4324(2) 0.11788(14) 0.0656(5) Uani 1 1 d . . . . .
H00P H -0.0491 1.5106 0.1182 0.079 Uiso 1 1 calc R U . . .
C00Q C -0.09870(7) 1.2809(2) 0.13110(14) 0.0685(6) Uani 1 1 d . . . . .
H00Q H -0.1188 1.3576 0.1302 0.082 Uiso 1 1 calc R U . . .
C00R C -0.08792(6) 1.0363(2) 0.13953(13) 0.0653(5) Uani 1 1 d . . . . .
H00R H -0.1005 0.9493 0.1456 0.078 Uiso 1 1 calc R U . . .
C00S C -0.11674(7) 1.1518(3) 0.13956(14) 0.0712(6) Uani 1 1 d . . . . .
H00S H -0.1485 1.1420 0.1454 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




O001 C00C 1.4287(16) . ?
N002 C006 1.2666(19) . ?
N002 C005 1.4757(18) . ?
C003 C00B 1.394(2) . ?
C003 C007 1.407(2) . ?
C003 C006 1.478(2) . ?
C004 C00I 1.380(2) . ?
C004 C00H 1.389(2) . ?
C004 C00C 1.513(2) . ?
C005 C00J 1.517(2) . ?
C005 C00C 1.525(2) . ?
C007 C008 1.427(2) . ?
C007 C00G 1.443(2) . ?
C008 C009 1.422(2) . ?
C008 C00A 1.432(2) . ?
C009 C00F 1.396(2) . ?
C009 C00M 1.438(2) . ?
C00A C00D 1.415(2) . ?
C00A C00E 1.425(2) . ?
C00B C00F 1.377(2) . ?
C00D C00R 1.402(2) . ?
C00D C00K 1.432(2) . ?
C00E C00Q 1.402(2) . ?
C00E C00P 1.422(2) . ?
C00G C00K 1.344(2) . ?
C00H C00O 1.377(2) . ?
C00I C00L 1.380(2) . ?
C00L C00N 1.374(2) . ?
C00M C00P 1.337(2) . ?
C00N C00O 1.375(3) . ?
C00Q C00S 1.370(3) . ?
C00R C00S 1.380(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






C006 N002 C005 117.49(13) . . ?
C00B C003 C007 119.55(14) . . ?
C00B C003 C006 118.72(13) . . ?
C007 C003 C006 121.67(14) . . ?
C00I C004 C00H 118.04(15) . . ?
C00I C004 C00C 121.20(14) . . ?
C00H C004 C00C 120.76(16) . . ?
N002 C005 C00J 108.88(12) . . ?
N002 C005 C00C 109.40(12) . . ?
C00J C005 C00C 112.01(12) . . ?
N002 C006 C003 122.93(15) . . ?
C003 C007 C008 119.04(14) . . ?
C003 C007 C00G 123.55(14) . . ?
C008 C007 C00G 117.38(14) . . ?
C009 C008 C007 120.26(14) . . ?
C009 C008 C00A 119.24(14) . . ?
C007 C008 C00A 120.51(15) . . ?
C00F C009 C008 118.53(14) . . ?
C00F C009 C00M 122.53(16) . . ?
C008 C009 C00M 118.94(15) . . ?
C00D C00A C00E 119.98(15) . . ?
C00D C00A C008 119.97(14) . . ?
C00E C00A C008 120.05(15) . . ?
C00F C00B C003 121.48(15) . . ?
O001 C00C C004 111.15(12) . . ?
O001 C00C C005 106.00(12) . . ?
C004 C00C C005 113.24(12) . . ?
C00R C00D C00A 118.69(16) . . ?
C00R C00D C00K 122.98(17) . . ?
C00A C00D C00K 118.33(14) . . ?
C00Q C00E C00P 123.27(17) . . ?
C00Q C00E C00A 118.31(18) . . ?
C00P C00E C00A 118.41(15) . . ?
C00B C00F C009 121.11(15) . . ?
C00K C00G C007 121.76(15) . . ?
C00O C00H C004 121.26(18) . . ?
C00L C00I C004 120.82(16) . . ?
C00G C00K C00D 122.04(16) . . ?
C00N C00L C00I 120.39(18) . . ?
C00P C00M C009 121.10(17) . . ?
C00L C00N C00O 119.65(17) . . ?
C00N C00O C00H 119.84(17) . . ?
C00M C00P C00E 122.27(16) . . ?
C00S C00Q C00E 121.54(18) . . ?
C00S C00R C00D 121.18(19) . . ?
C00Q C00S C00R 120.28(17) . . ?

_refine_diff_density_max         0.185

_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.046





