# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_exp_9466
_database_code_depnum_ccdc_archive 'CCDC 1865244'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 N O3'
_chemical_formula_weight         447.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.5256(3)
_cell_length_b                   16.9053(5)
_cell_length_c                   8.9274(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.310(4)
_cell_angle_gamma                90
_cell_volume                     1190.37(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2808
_cell_measurement_theta_min      5.6330
_cell_measurement_theta_max      71.1340

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.638
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_T_min  0.82241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4216
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.233
_diffrn_reflns_theta_max         67.249
_diffrn_reflns_theta_full        67.249
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_point_group_measured_fraction_full 0.741
_reflns_number_total             3161
_reflns_number_gt                3081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.430
_reflns_Friedel_fraction_max     0.463
_reflns_Friedel_fraction_full    0.463

_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0601P)²+0.1634P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0103(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(13)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.1573(2) 0.62839(12) 0.6959(2) 0.0368(4) Uani 1 1 d . . . . .
O1 O 0.1799(4) 0.58728(16) 0.9516(3) 0.0897(9) Uani 1 1 d . . . . .
O2 O 0.1637(4) 0.43596(15) 0.8008(3) 0.0770(7) Uani 1 1 d . . . . .
H2 H 0.212093 0.414963 0.889266 0.116 Uiso 1 1 calc R U . . .
O3 O 0.4792(5) 0.4287(3) 0.9801(5) 0.1289(14) Uani 1 1 d . . . . .
C1 C 0.3299(3) 0.75508(16) 0.6181(3) 0.0468(6) Uani 1 1 d . . . . .
H1 H 0.374193 0.704096 0.634982 0.056 Uiso 1 1 calc R U . . .
C2 C 0.4188(4) 0.8156(2) 0.5811(4) 0.0614(8) Uani 1 1 d . . . . .
H2A H 0.521725 0.804770 0.571935 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3568(4) 0.8913(2) 0.5580(5) 0.0697(9) Uani 1 1 d . . . . .
H3 H 0.416350 0.931372 0.531435 0.084 Uiso 1 1 calc R U . . .
C4 C 0.2051(4) 0.90783(19) 0.5741(4) 0.0640(8) Uani 1 1 d . . . . .
H4 H 0.162807 0.959166 0.559698 0.077 Uiso 1 1 calc R U . . .
C5 C 0.1175(3) 0.84794(16) 0.6117(4) 0.0507(6) Uani 1 1 d . . . . .
H5 H 0.017127 0.859626 0.625218 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1753(3) 0.77023(15) 0.6299(3) 0.0390(5) Uani 1 1 d . . . . .
C7 C 0.0703(3) 0.70688(14) 0.6758(3) 0.0371(5) Uani 1 1 d . . . . .
C8 C -0.1096(3) 0.69389(15) 0.5449(3) 0.0389(5) Uani 1 1 d . . . . .
C9 C -0.1813(3) 0.74167(18) 0.4095(3) 0.0476(6) Uani 1 1 d . . . . .
H9 H -0.120642 0.784495 0.394118 0.057 Uiso 1 1 calc R U . . .
C10 C -0.3425(3) 0.7261(2) 0.2972(4) 0.0610(8) Uani 1 1 d . . . . .
H10 H -0.387882 0.758295 0.206373 0.073 Uiso 1 1 calc R U . . .
C11 C -0.4362(3) 0.6643(2) 0.3172(4) 0.0629(8) Uani 1 1 d . . . . .
H11 H -0.544354 0.654332 0.241084 0.076 Uiso 1 1 calc R U . . .
C12 C -0.3667(4) 0.61687(18) 0.4533(4) 0.0603(7) Uani 1 1 d . . . . .
H12 H -0.429942 0.575412 0.470018 0.072 Uiso 1 1 calc R U . . .
C13 C -0.2050(3) 0.63058(17) 0.5639(4) 0.0503(6) Uani 1 1 d . . . . .
H13 H -0.158813 0.597091 0.652488 0.060 Uiso 1 1 calc R U . . .
C14 C 0.0620(3) 0.73591(15) 0.8378(3) 0.0422(5) Uani 1 1 d . . . . .
C15 C -0.0869(4) 0.7445(2) 0.8609(4) 0.0570(7) Uani 1 1 d . . . . .
H15 H -0.188639 0.729718 0.779483 0.068 Uiso 1 1 calc R U . . .
C16 C -0.0871(5) 0.7754(2) 1.0059(5) 0.0739(10) Uani 1 1 d . . . . .
H16 H -0.189050 0.780745 1.020225 0.089 Uiso 1 1 calc R U . . .
C17 C 0.0605(5) 0.7979(2) 1.1267(4) 0.0671(8) Uani 1 1 d . . . . .
H17 H 0.059981 0.817678 1.223676 0.081 Uiso 1 1 calc R U . . .
C18 C 0.2085(4) 0.7908(2) 1.1033(4) 0.0669(9) Uani 1 1 d . . . . .
H18 H 0.309580 0.806581 1.184515 0.080 Uiso 1 1 calc R U . . .
C19 C 0.2107(3) 0.7606(2) 0.9607(3) 0.0594(8) Uani 1 1 d . . . . .
H19 H 0.313022 0.756690 0.946594 0.071 Uiso 1 1 calc R U . . .
C20 C 0.1728(3) 0.58696(14) 0.5626(3) 0.0351(5) Uani 1 1 d . . . . .
C21 C 0.1349(3) 0.61197(17) 0.4060(3) 0.0434(5) Uani 1 1 d . . . . .
H21 H 0.092700 0.662539 0.373606 0.052 Uiso 1 1 calc R U . . .
C22 C 0.1612(3) 0.5596(2) 0.2974(3) 0.0526(7) Uani 1 1 d . . . . .
H22 H 0.134706 0.575496 0.190895 0.063 Uiso 1 1 calc R U . . .
C23 C 0.2251(3) 0.48520(19) 0.3437(4) 0.0560(7) Uani 1 1 d . . . . .
H23 H 0.242592 0.451475 0.269200 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2634(3) 0.46035(16) 0.5012(4) 0.0496(6) Uani 1 1 d . . . . .
H24 H 0.306148 0.409844 0.533406 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2373(3) 0.51163(15) 0.6099(3) 0.0382(5) Uani 1 1 d . . . . .
C26 C 0.2627(3) 0.49900(15) 0.7830(3) 0.0454(6) Uani 1 1 d . . . . .
C27 C 0.1961(3) 0.57749(17) 0.8253(3) 0.0475(6) Uani 1 1 d . . . . .
C28 C 0.4471(4) 0.4867(2) 0.8950(4) 0.0672(9) Uani 1 1 d . . . . .
C29 C 0.5757(5) 0.5455(4) 0.8938(6) 0.1016(15) Uani 1 1 d . . . . .
H29A H 0.568703 0.551105 0.783338 0.122 Uiso 1 1 calc R U . . .
H29B H 0.546257 0.596207 0.926751 0.122 Uiso 1 1 calc R U . . .
C30 C 0.7523(7) 0.5277(6) 0.9972(11) 0.179(4) Uani 1 1 d . . . . .
H30A H 0.762772 0.524000 1.107950 0.268 Uiso 1 1 calc R U . . .
H30B H 0.824636 0.569099 0.987007 0.268 Uiso 1 1 calc R U . . .
H30C H 0.784964 0.478336 0.964422 0.268 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 C27 1.376(3) . ?
N1 C20 1.430(3) . ?
N1 C7 1.497(3) . ?
O1 C27 1.199(3) . ?
O2 C26 1.405(3) . ?
O3 C28 1.207(5) . ?
C1 C6 1.386(3) . ?
C1 C2 1.386(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.383(5) . ?
C4 C5 1.373(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.547(3) . ?
C7 C8 1.551(3) . ?
C7 C14 1.554(3) . ?
C8 C9 1.388(4) . ?
C8 C13 1.393(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.367(5) . ?
C11 C12 1.387(5) . ?
C12 C13 1.377(4) . ?
C14 C15 1.369(4) . ?
C14 C19 1.389(4) . ?
C15 C16 1.396(4) . ?
C16 C17 1.364(5) . ?
C17 C18 1.361(5) . ?
C18 C19 1.378(4) . ?
C20 C21 1.376(3) . ?
C20 C25 1.388(4) . ?
C21 C22 1.393(4) . ?
C22 C23 1.370(5) . ?
C23 C24 1.382(4) . ?
C24 C25 1.381(4) . ?
C25 C26 1.492(3) . ?
C26 C28 1.524(4) . ?
C26 C27 1.545(4) . ?
C28 C29 1.483(6) . ?
C29 C30 1.467(7) . ?

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
C27 N1 C20 108.9(2) . . ?
C27 N1 C7 127.24(19) . . ?
C20 N1 C7 122.18(18) . . ?
C6 C1 C2 120.2(3) . . ?
C3 C2 C1 120.7(3) . . ?
C2 C3 C4 119.7(3) . . ?
C5 C4 C3 119.5(3) . . ?
C4 C5 C6 121.6(2) . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 123.7(2) . . ?
C5 C6 C7 118.0(2) . . ?
N1 C7 C6 109.58(17) . . ?
N1 C7 C8 105.55(19) . . ?
C6 C7 C8 113.88(18) . . ?
N1 C7 C14 111.33(18) . . ?
C6 C7 C14 105.25(19) . . ?
C8 C7 C14 111.37(18) . . ?
C9 C8 C13 117.9(2) . . ?
C9 C8 C7 123.8(2) . . ?
C13 C8 C7 118.3(2) . . ?
C10 C9 C8 120.6(3) . . ?
C11 C10 C9 121.3(3) . . ?
C10 C11 C12 118.7(3) . . ?
C13 C12 C11 120.6(3) . . ?
C12 C13 C8 121.0(3) . . ?
C15 C14 C19 118.0(2) . . ?
C15 C14 C7 123.1(2) . . ?
C19 C14 C7 118.7(2) . . ?
C14 C15 C16 120.5(3) . . ?
C17 C16 C15 120.8(3) . . ?
C18 C17 C16 119.0(3) . . ?
C17 C18 C19 120.9(3) . . ?
C18 C19 C14 120.9(3) . . ?
C21 C20 C25 120.3(2) . . ?
C21 C20 N1 129.4(2) . . ?
C25 C20 N1 110.36(19) . . ?
C20 C21 C22 118.3(3) . . ?
C23 C22 C21 121.6(3) . . ?
C22 C23 C24 119.9(2) . . ?
C25 C24 C23 119.0(3) . . ?
C24 C25 C20 120.9(2) . . ?
C24 C25 C26 129.7(2) . . ?
C20 C25 C26 109.3(2) . . ?
O2 C26 C25 111.6(2) . . ?
O2 C26 C28 109.7(2) . . ?
C25 C26 C28 114.0(2) . . ?
O2 C26 C27 109.4(2) . . ?
C25 C26 C27 102.0(2) . . ?
C28 C26 C27 109.8(2) . . ?
O1 C27 N1 128.8(3) . . ?
O1 C27 C26 122.2(2) . . ?
N1 C27 C26 109.0(2) . . ?
O3 C28 C29 123.9(4) . . ?
O3 C28 C26 117.1(4) . . ?
C29 C28 C26 119.1(3) . . ?
C30 C29 C28 116.3(5) . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.030



