# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20160708e_0m
_database_code_depnum_ccdc_archive 'CCDC 1576256'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.6879(3)
_cell_length_b                   13.3936(5)
_cell_length_c                   15.6960(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3590(10)
_cell_angle_gamma                90.00
_cell_volume                     1572.46(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      3.0420
_cell_measurement_theta_max      27.4697

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9877
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24512
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2760
_reflns_number_gt                2223
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0574P)²+0.3894P] 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       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2760
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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
C1 C 0.5185(2) 0.09821(12) 0.85096(10) 0.0409(4) Uani 1 1 d . . .
H1 H 0.5205 0.0310 0.8362 0.049 Uiso 1 1 calc R . .
C2 C 0.40521(19) 0.12642(11) 0.90602(9) 0.0350(4) Uani 1 1 d . . .
C3 C 0.40350(18) 0.22537(11) 0.93078(9) 0.0328(3) Uani 1 1 d . . .
C4 C 0.5113(2) 0.39882(12) 0.91274(11) 0.0429(4) Uani 1 1 d . . .
H4 H 0.4444 0.4242 0.9502 0.051 Uiso 1 1 calc R . .
C5 C 0.6101(2) 0.46204(14) 0.87510(13) 0.0524(5) Uani 1 1 d . . .
H5 H 0.6087 0.5302 0.8864 0.063 Uiso 1 1 calc R . .
C6 C 0.7140(2) 0.42553(14) 0.81944(12) 0.0535(5) Uani 1 1 d . . .
H6 H 0.7807 0.4694 0.7939 0.064 Uiso 1 1 calc R . .
C7 C 0.7175(2) 0.32589(14) 0.80271(11) 0.0478(4) Uani 1 1 d . . .
H7 H 0.7885 0.3022 0.7665 0.057 Uiso 1 1 calc R . .
C8 C 0.6148(2) 0.25801(12) 0.83961(10) 0.0375(4) Uani 1 1 d . . .
C9 C 0.50892(19) 0.29455(11) 0.89561(9) 0.0344(4) Uani 1 1 d . . .
C10 C 0.29433(19) 0.25967(10) 0.99279(9) 0.0323(3) Uani 1 1 d . . .
C11 C 0.1370(2) 0.31266(12) 0.96318(10) 0.0410(4) Uani 1 1 d . . .
H11 H 0.1008 0.3283 0.9040 0.049 Uiso 1 1 calc R . .
C12 C 0.0321(2) 0.34304(12) 1.01951(10) 0.0412(4) Uani 1 1 d . . .
H12 H -0.0731 0.3783 0.9982 0.049 Uiso 1 1 calc R . .
C13 C 0.08555(19) 0.32044(11) 1.10758(10) 0.0350(4) Uani 1 1 d . . .
C14 C 0.2432(2) 0.26857(12) 1.13840(10) 0.0383(4) Uani 1 1 d . . .
H14 H 0.2802 0.2539 1.1977 0.046 Uiso 1 1 calc R . .
C15 C 0.34578(19) 0.23855(11) 1.08173(10) 0.0368(4) Uani 1 1 d . . .
H15 H 0.4512 0.2036 1.1034 0.044 Uiso 1 1 calc R . .
C16 C -0.1684(2) 0.40077(15) 1.14136(13) 0.0576(5) Uani 1 1 d . . .
H16A H -0.1418 0.4636 1.1178 0.086 Uiso 1 1 calc R . .
H16B H -0.2202 0.4124 1.1906 0.086 Uiso 1 1 calc R . .
H16C H -0.2514 0.3643 1.0972 0.086 Uiso 1 1 calc R . .
C17 C 0.2834(2) 0.05113(11) 0.93316(10) 0.0380(4) Uani 1 1 d . . .
H17 H 0.2928 0.0569 0.9963 0.046 Uiso 1 1 calc R . .
C18 C 0.0876(2) 0.06066(14) 0.88508(13) 0.0540(5) Uani 1 1 d . . .
H18A H 0.0765 0.0915 0.8281 0.065 Uiso 1 1 calc R . .
H18B H 0.0214 0.1000 0.9187 0.065 Uiso 1 1 calc R . .
C19 C 0.0207(3) -0.04707(15) 0.87579(15) 0.0634(5) Uani 1 1 d . . .
H19A H -0.0747 -0.0568 0.9060 0.076 Uiso 1 1 calc R . .
H19B H -0.0229 -0.0648 0.8146 0.076 Uiso 1 1 calc R . .
C20 C 0.1819(3) -0.10810(14) 0.91714(13) 0.0548(5) Uani 1 1 d . . .
H20A H 0.1810 -0.1242 0.9773 0.066 Uiso 1 1 calc R . .
H20B H 0.1842 -0.1698 0.8850 0.066 Uiso 1 1 calc R . .
N1 N 0.62128(18) 0.15910(10) 0.81895(9) 0.0440(4) Uani 1 1 d . . .
O1 O -0.00840(15) 0.34464(9) 1.16875(7) 0.0487(3) Uani 1 1 d . . .
O2 O 0.33310(16) -0.04754(8) 0.91374(8) 0.0497(3) Uani 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
C1 N1 1.313(2) . ?
C1 C2 1.413(2) . ?
C2 C3 1.382(2) . ?
C2 C17 1.503(2) . ?
C3 C9 1.424(2) . ?
C3 C10 1.497(2) . ?
C4 C5 1.360(2) . ?
C4 C9 1.421(2) . ?
C5 C6 1.401(3) . ?
C6 C7 1.362(3) . ?
C7 C8 1.413(2) . ?
C8 N1 1.368(2) . ?
C8 C9 1.416(2) . ?
C10 C15 1.389(2) . ?
C10 C11 1.386(2) . ?
C11 C12 1.388(2) . ?
C12 C13 1.382(2) . ?
C13 O1 1.3671(17) . ?
C13 C14 1.384(2) . ?
C14 C15 1.378(2) . ?
C16 O1 1.421(2) . ?
C17 O2 1.4281(18) . ?
C17 C18 1.525(2) . ?
C18 C19 1.527(3) . ?
C19 C20 1.501(3) . ?
C20 O2 1.429(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
N1 C1 C2 125.34(15) . . ?
C3 C2 C1 118.40(14) . . ?
C3 C2 C17 121.10(13) . . ?
C1 C2 C17 120.43(14) . . ?
C2 C3 C9 118.16(13) . . ?
C2 C3 C10 121.36(13) . . ?
C9 C3 C10 120.49(13) . . ?
C5 C4 C9 120.89(16) . . ?
C4 C5 C6 120.64(17) . . ?
C7 C6 C5 120.13(16) . . ?
C6 C7 C8 120.89(16) . . ?
N1 C8 C7 118.11(14) . . ?
N1 C8 C9 122.68(14) . . ?
C7 C8 C9 119.21(15) . . ?
C8 C9 C4 118.22(14) . . ?
C8 C9 C3 118.43(14) . . ?
C4 C9 C3 123.34(14) . . ?
C15 C10 C11 117.70(13) . . ?
C15 C10 C3 121.25(13) . . ?
C11 C10 C3 121.05(13) . . ?
C12 C11 C10 121.78(14) . . ?
C13 C12 C11 119.40(14) . . ?
O1 C13 C12 124.59(14) . . ?
O1 C13 C14 115.84(14) . . ?
C12 C13 C14 119.57(14) . . ?
C15 C14 C13 120.43(14) . . ?
C14 C15 C10 121.12(14) . . ?
O2 C17 C2 110.19(12) . . ?
O2 C17 C18 104.72(13) . . ?
C2 C17 C18 114.32(13) . . ?
C17 C18 C19 103.90(15) . . ?
C20 C19 C18 104.30(15) . . ?
O2 C20 C19 105.81(15) . . ?
C1 N1 C8 116.90(13) . . ?
C13 O1 C16 118.29(13) . . ?
C20 O2 C17 104.90(12) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047
