# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1525011'
_audit_update_record             
;
2016-12-30 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_absolute_configuration ' unk '

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.0521(16)
_cell_length_b                   10.418(2)
_cell_length_c                   10.027(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.73(3)
_cell_angle_gamma                90.00
_cell_volume                     835.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2155
_cell_measurement_theta_min      2.8318
_cell_measurement_theta_max      27.4817

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.081
_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      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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6411
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3594
_reflns_number_gt                2677
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0403P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(11)
_refine_ls_number_reflns         3594
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.991
_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 0.39153(15) 0.65880(13) 0.00977(14) 0.0635(4) Uani 1 1 d . . .
N1 N 0.54586(14) 0.79875(12) 0.15424(12) 0.0384(3) Uani 1 1 d . . .
C1 C 0.40941(19) 0.75736(18) 0.07230(17) 0.0438(4) Uani 1 1 d . . .
O2 O 0.28684(13) 0.84690(13) 0.06830(13) 0.0561(4) Uani 1 1 d . . .
C2 C 0.3501(2) 0.9600(2) 0.1398(2) 0.0586(5) Uani 1 1 d . . .
H2A H 0.2728 0.9887 0.2009 0.070 Uiso 1 1 calc R . .
H2B H 0.3660 1.0289 0.0776 0.070 Uiso 1 1 calc R . .
C3 C 0.5141(2) 0.92147(19) 0.2162(2) 0.0564(5) Uani 1 1 d . . .
H3A H 0.6011 0.9833 0.2042 0.068 Uiso 1 1 calc R . .
H3B H 0.5049 0.9118 0.3112 0.068 Uiso 1 1 calc R . .
C4 C 0.69440(18) 0.72582(15) 0.17735(15) 0.0357(4) Uani 1 1 d . . .
C5 C 0.85923(19) 0.77403(16) 0.13390(15) 0.0390(4) Uani 1 1 d . . .
C6 C 0.8345(2) 0.8179(2) -0.01298(16) 0.0573(5) Uani 1 1 d . . .
H6A H 0.9389 0.8483 -0.0383 0.086 Uiso 1 1 calc R . .
H6B H 0.7535 0.8858 -0.0233 0.086 Uiso 1 1 calc R . .
H6C H 0.7957 0.7470 -0.0694 0.086 Uiso 1 1 calc R . .
C7 C 0.9615(2) 0.65388(18) 0.15147(18) 0.0475(4) Uani 1 1 d . . .
H7A H 1.0713 0.6468 0.1320 0.057 Uiso 1 1 calc R . .
C8 C 0.8752(2) 0.55873(17) 0.19849(17) 0.0469(4) Uani 1 1 d . . .
H8A H 0.9159 0.4762 0.2163 0.056 Uiso 1 1 calc R . .
C9 C 0.70637(19) 0.60219(16) 0.21836(15) 0.0387(4) Uani 1 1 d . . .
C10 C 0.58016(19) 0.52272(17) 0.27489(15) 0.0426(4) Uani 1 1 d . . .
C11 C 0.5775(2) 0.38995(19) 0.25916(18) 0.0572(5) Uani 1 1 d . . .
H11A H 0.6529 0.3508 0.2086 0.069 Uiso 1 1 calc R . .
C12 C 0.4634(3) 0.3157(2) 0.3181(2) 0.0792(8) Uani 1 1 d . . .
H12A H 0.4632 0.2270 0.3074 0.095 Uiso 1 1 calc R . .
C13 C 0.3503(3) 0.3726(3) 0.3926(3) 0.0878(8) Uani 1 1 d . . .
H13A H 0.2732 0.3227 0.4316 0.105 Uiso 1 1 calc R . .
C14 C 0.3519(3) 0.5013(3) 0.4087(2) 0.0777(7) Uani 1 1 d . . .
H14A H 0.2757 0.5396 0.4592 0.093 Uiso 1 1 calc R . .
C15 C 0.4646(2) 0.5765(2) 0.35133(18) 0.0580(5) Uani 1 1 d . . .
H15A H 0.4635 0.6649 0.3639 0.070 Uiso 1 1 calc R . .
C16 C 0.93562(17) 0.87990(15) 0.22905(15) 0.0381(4) Uani 1 1 d . . .
C17 C 0.9209(2) 1.00933(18) 0.20005(19) 0.0505(5) Uani 1 1 d . . .
H17A H 0.8653 1.0358 0.1181 0.061 Uiso 1 1 calc R . .
C18 C 0.9892(2) 1.1010(2) 0.2932(2) 0.0642(6) Uani 1 1 d . . .
H18A H 0.9765 1.1880 0.2735 0.077 Uiso 1 1 calc R . .
C19 C 1.0745(3) 1.0632(2) 0.4131(2) 0.0691(6) Uani 1 1 d . . .
H19A H 1.1206 1.1243 0.4742 0.083 Uiso 1 1 calc R . .
C20 C 1.0913(3) 0.9368(2) 0.4420(2) 0.0714(6) Uani 1 1 d . . .
H20A H 1.1500 0.9111 0.5230 0.086 Uiso 1 1 calc R . .
C21 C 1.0219(2) 0.8457(2) 0.35237(18) 0.0547(5) Uani 1 1 d . . .
H21A H 1.0332 0.7593 0.3749 0.066 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 C1 1.203(2) . ?
N1 C1 1.3626(19) . ?
N1 C4 1.4130(19) . ?
N1 C3 1.457(2) . ?
C1 O2 1.355(2) . ?
O2 C2 1.441(2) . ?
C2 C3 1.501(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.352(2) . ?
C4 C5 1.529(2) . ?
C5 C7 1.497(2) . ?
C5 C6 1.533(2) . ?
C5 C16 1.539(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.329(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.468(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.475(2) . ?
C10 C15 1.391(3) . ?
C10 C11 1.392(2) . ?
C11 C12 1.385(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.350(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.382(2) . ?
C16 C21 1.392(2) . ?
C17 C18 1.403(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.352(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 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 C4 122.41(14) . . ?
C1 N1 C3 111.41(13) . . ?
C4 N1 C3 126.13(13) . . ?
O1 C1 O2 122.00(14) . . ?
O1 C1 N1 128.55(16) . . ?
O2 C1 N1 109.45(16) . . ?
C1 O2 C2 109.55(12) . . ?
O2 C2 C3 105.88(15) . . ?
O2 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
O2 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
N1 C3 C2 101.84(14) . . ?
N1 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
N1 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
C9 C4 N1 126.22(14) . . ?
C9 C4 C5 111.48(13) . . ?
N1 C4 C5 121.52(14) . . ?
C7 C5 C4 100.12(13) . . ?
C7 C5 C6 111.71(15) . . ?
C4 C5 C6 110.64(12) . . ?
C7 C5 C16 110.60(13) . . ?
C4 C5 C16 110.85(13) . . ?
C6 C5 C16 112.30(14) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 111.22(15) . . ?
C8 C7 H7A 124.4 . . ?
C5 C7 H7A 124.4 . . ?
C7 C8 C9 110.44(15) . . ?
C7 C8 H8A 124.8 . . ?
C9 C8 H8A 124.8 . . ?
C4 C9 C8 106.65(14) . . ?
C4 C9 C10 128.61(15) . . ?
C8 C9 C10 124.73(15) . . ?
C15 C10 C11 117.40(17) . . ?
C15 C10 C9 121.42(16) . . ?
C11 C10 C9 121.11(17) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15A 119.4 . . ?
C10 C15 H15A 119.4 . . ?
C17 C16 C21 117.29(16) . . ?
C17 C16 C5 123.42(14) . . ?
C21 C16 C5 119.27(15) . . ?
C16 C17 C18 120.49(18) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C20 C19 C18 119.70(19) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C16 121.62(19) . . ?
C20 C21 H21A 119.2 . . ?
C16 C21 H21A 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
C4 N1 C1 O1 0.2(3) . . . . ?
C3 N1 C1 O1 -177.41(18) . . . . ?
C4 N1 C1 O2 -179.49(13) . . . . ?
C3 N1 C1 O2 2.91(19) . . . . ?
O1 C1 O2 C2 -173.38(17) . . . . ?
N1 C1 O2 C2 6.32(19) . . . . ?
C1 O2 C2 C3 -12.6(2) . . . . ?
C1 N1 C3 C2 -10.2(2) . . . . ?
C4 N1 C3 C2 172.31(15) . . . . ?
O2 C2 C3 N1 13.24(19) . . . . ?
C1 N1 C4 C9 -52.9(2) . . . . ?
C3 N1 C4 C9 124.36(18) . . . . ?
C1 N1 C4 C5 116.16(17) . . . . ?
C3 N1 C4 C5 -66.6(2) . . . . ?
C9 C4 C5 C7 2.69(16) . . . . ?
N1 C4 C5 C7 -167.82(13) . . . . ?
C9 C4 C5 C6 120.64(16) . . . . ?
N1 C4 C5 C6 -49.86(19) . . . . ?
C9 C4 C5 C16 -114.09(15) . . . . ?
N1 C4 C5 C16 75.41(17) . . . . ?
C4 C5 C7 C8 -1.49(17) . . . . ?
C6 C5 C7 C8 -118.65(16) . . . . ?
C16 C5 C7 C8 115.46(15) . . . . ?
C5 C7 C8 C9 -0.1(2) . . . . ?
N1 C4 C9 C8 167.14(14) . . . . ?
C5 C4 C9 C8 -2.82(16) . . . . ?
N1 C4 C9 C10 -13.9(3) . . . . ?
C5 C4 C9 C10 176.16(14) . . . . ?
C7 C8 C9 C4 1.83(19) . . . . ?
C7 C8 C9 C10 -177.21(15) . . . . ?
C4 C9 C10 C15 -31.3(2) . . . . ?
C8 C9 C10 C15 147.56(17) . . . . ?
C4 C9 C10 C11 151.89(17) . . . . ?
C8 C9 C10 C11 -29.3(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 176.90(16) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C9 C10 C15 C14 -177.14(17) . . . . ?
C7 C5 C16 C17 150.40(16) . . . . ?
C4 C5 C16 C17 -99.48(17) . . . . ?
C6 C5 C16 C17 24.9(2) . . . . ?
C7 C5 C16 C21 -30.8(2) . . . . ?
C4 C5 C16 C21 79.29(19) . . . . ?
C6 C5 C16 C21 -156.38(16) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
C5 C16 C17 C18 177.98(15) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C20 C21 C16 1.2(3) . . . . ?
C17 C16 C21 C20 -0.4(3) . . . . ?
C5 C16 C21 C20 -179.29(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.029
