# 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. 
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#######################################################################

data_wmj18002_0m
_database_code_depnum_ccdc_archive 'CCDC 1834383'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_audit_creation_date             2018-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 N2 O3'
_chemical_formula_sum            'C24 H26 N2 O3'
_chemical_formula_weight         390.47
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.2146(4)
_cell_length_b                   11.7243(5)
_cell_length_c                   10.2644(4)
_cell_angle_alpha                90
_cell_angle_beta                 119.315(2)
_cell_angle_gamma                90
_cell_volume                     1071.84(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      60.858
_cell_measurement_theta_min      4.320
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1482 before and 0.0743 after correction. The Ratio of minimum to maximum transmission is 0.7587. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13110
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.888
_diffrn_reflns_theta_min         4.319
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4589
_reflns_number_total             4904
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4904
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.1539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.51785(18) 0.53011(16) 0.70596(18) 0.0435(4) Uani 1 1 d . . . . .
O2 O 0.8880(3) 0.67390(19) 0.8621(2) 0.0756(7) Uani 1 1 d . . . . .
O3 O 0.7885(2) 0.55960(15) 0.96592(17) 0.0412(4) Uani 1 1 d . . . . .
N1 N 0.75445(19) 0.51352(16) 0.73905(18) 0.0327(4) Uani 1 1 d . . . . .
N2 N 0.85416(19) 0.49060(15) 0.68470(18) 0.0310(4) Uani 1 1 d . . . . .
C1 C 0.5999(2) 0.49599(19) 0.6607(2) 0.0323(4) Uani 1 1 d . . . . .
C2 C 0.5434(2) 0.43657(18) 0.5117(2) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.455095 0.389122 0.494938 0.036 Uiso 1 1 calc R . . . .
C3 C 0.6632(2) 0.35490(17) 0.5165(2) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.675384 0.292406 0.587836 0.035 Uiso 1 1 calc R . . . .
C4 C 0.6181(2) 0.29868(19) 0.3665(2) 0.0342(4) Uani 1 1 d . . . . .
H4A H 0.527348 0.251351 0.335663 0.041 Uiso 1 1 calc R . . . .
H4B H 0.594262 0.357971 0.289390 0.041 Uiso 1 1 calc R . . . .
C5 C 0.7463(3) 0.22447(18) 0.3799(2) 0.0347(5) Uani 1 1 d . . . . .
H5A H 0.766171 0.162946 0.453392 0.042 Uiso 1 1 calc R . . . .
H5B H 0.717072 0.188550 0.282183 0.042 Uiso 1 1 calc R . . . .
C6 C 0.8861(2) 0.29345(17) 0.4286(2) 0.0302(4) Uani 1 1 d . . . . .
C7 C 0.9883(3) 0.26756(18) 0.3788(3) 0.0370(5) Uani 1 1 d . . . . .
H7 H 0.967137 0.206253 0.310856 0.044 Uiso 1 1 calc R . . . .
C8 C 1.1181(3) 0.3289(2) 0.4261(3) 0.0420(5) Uani 1 1 d . . . . .
H8 H 1.185266 0.310099 0.390291 0.050 Uiso 1 1 calc R . . . .
C9 C 1.1517(3) 0.4184(2) 0.5265(3) 0.0432(5) Uani 1 1 d . . . . .
H9 H 1.242253 0.460247 0.560352 0.052 Uiso 1 1 calc R . . . .
C10 C 1.0526(2) 0.44596(19) 0.5763(3) 0.0371(5) Uani 1 1 d . . . . .
H10 H 1.075537 0.507064 0.644917 0.045 Uiso 1 1 calc R . . . .
C11 C 0.9188(2) 0.38538(17) 0.5274(2) 0.0282(4) Uani 1 1 d . . . . .
C12 C 0.8120(2) 0.41565(16) 0.5803(2) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.4871(2) 0.52503(19) 0.3876(2) 0.0321(4) Uani 1 1 d . . . . .
C14 C 0.5646(3) 0.62538(19) 0.4004(2) 0.0367(5) Uani 1 1 d . . . . .
H14 H 0.656550 0.639733 0.489144 0.044 Uiso 1 1 calc R . . . .
C15 C 0.5103(3) 0.7052(2) 0.2857(3) 0.0415(5) Uani 1 1 d . . . . .
H15 H 0.565656 0.773181 0.297485 0.050 Uiso 1 1 calc R . . . .
C16 C 0.3766(3) 0.6873(2) 0.1542(3) 0.0484(6) Uani 1 1 d . . . . .
C17 C 0.2997(3) 0.5857(3) 0.1406(3) 0.0540(7) Uani 1 1 d . . . . .
H17 H 0.209113 0.570398 0.050847 0.065 Uiso 1 1 calc R . . . .
C18 C 0.3533(3) 0.5069(3) 0.2555(3) 0.0475(6) Uani 1 1 d . . . . .
H18 H 0.297773 0.439125 0.244050 0.057 Uiso 1 1 calc R . . . .
C19 C 0.3171(4) 0.7758(3) 0.0317(3) 0.0708(10) Uani 1 1 d . . . . .
H19A H 0.344047 0.852058 0.075978 0.106 Uiso 1 1 calc GR . . . .
H19B H 0.207620 0.769264 -0.027253 0.106 Uiso 1 1 calc GR . . . .
H19C H 0.361085 0.763347 -0.033288 0.106 Uiso 1 1 calc GR . . . .
C20 C 0.8179(3) 0.5929(2) 0.8620(2) 0.0390(5) Uani 1 1 d . . . . .
C21 C 0.8192(3) 0.6340(2) 1.0956(3) 0.0468(6) Uani 1 1 d . . . . .
C22 C 0.9854(4) 0.6523(4) 1.1891(4) 0.0817(12) Uani 1 1 d . . . . .
H22A H 1.037363 0.578877 1.207626 0.123 Uiso 1 1 calc GR . . . .
H22B H 1.007487 0.687004 1.284625 0.123 Uiso 1 1 calc GR . . . .
H22C H 1.019918 0.703069 1.136230 0.123 Uiso 1 1 calc GR . . . .
C23 C 0.7618(5) 0.5607(3) 1.1782(4) 0.0740(10) Uani 1 1 d . . . . .
H23A H 0.655046 0.544198 1.112697 0.111 Uiso 1 1 calc GR . . . .
H23B H 0.774798 0.601362 1.267210 0.111 Uiso 1 1 calc GR . . . .
H23C H 0.818345 0.489021 1.208336 0.111 Uiso 1 1 calc GR . . . .
C24 C 0.7288(5) 0.7409(3) 1.0395(4) 0.0793(11) Uani 1 1 d . . . . .
H24A H 0.771145 0.788798 0.991047 0.119 Uiso 1 1 calc GR . . . .
H24B H 0.731266 0.782475 1.123467 0.119 Uiso 1 1 calc GR . . . .
H24C H 0.624710 0.721472 0.967125 0.119 Uiso 1 1 calc GR . . . .


_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 1.208(2) . ?
O2 C20 1.189(3) . ?
O3 C20 1.301(3) . ?
O3 C21 1.490(3) . ?
N1 N2 1.406(2) . ?
N1 C1 1.392(3) . ?
N1 C20 1.442(3) . ?
N2 C12 1.286(2) . ?
C1 C2 1.514(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.536(3) . ?
C2 C13 1.520(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.524(3) . ?
C3 C12 1.507(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.498(3) . ?
C6 C7 1.402(3) . ?
C6 C11 1.404(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(3) . ?
C11 C12 1.480(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.392(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(4) . ?
C16 C17 1.396(4) . ?
C16 C19 1.509(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.502(4) . ?
C21 C23 1.513(4) . ?
C21 C24 1.495(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C20 O3 C21 121.63(19) . . ?
N2 N1 C20 111.61(16) . . ?
C1 N1 N2 125.42(16) . . ?
C1 N1 C20 119.84(17) . . ?
C12 N2 N1 116.67(17) . . ?
O1 C1 N1 122.23(19) . . ?
O1 C1 C2 123.16(19) . . ?
N1 C1 C2 114.53(16) . . ?
C1 C2 H2 107.2 . . ?
C1 C2 C3 110.54(17) . . ?
C1 C2 C13 109.47(17) . . ?
C3 C2 H2 107.2 . . ?
C13 C2 H2 107.2 . . ?
C13 C2 C3 114.83(16) . . ?
C2 C3 H3 106.9 . . ?
C4 C3 C2 113.30(17) . . ?
C4 C3 H3 106.9 . . ?
C12 C3 C2 109.72(16) . . ?
C12 C3 H3 106.9 . . ?
C12 C3 C4 112.68(16) . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.54(18) . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.04(17) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C7 C6 C5 121.33(19) . . ?
C7 C6 C11 118.22(19) . . ?
C11 C6 C5 120.45(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C6 C11 C12 119.41(17) . . ?
C10 C11 C6 119.69(18) . . ?
C10 C11 C12 120.90(18) . . ?
N2 C12 C3 122.71(17) . . ?
N2 C12 C11 117.56(17) . . ?
C11 C12 C3 119.66(17) . . ?
C14 C13 C2 122.36(18) . . ?
C14 C13 C18 117.6(2) . . ?
C18 C13 C2 120.0(2) . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 117.6(2) . . ?
C15 C16 C19 120.7(3) . . ?
C17 C16 C19 121.7(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 O3 128.3(2) . . ?
O2 C20 N1 121.9(2) . . ?
O3 C20 N1 109.80(19) . . ?
O3 C21 C22 109.4(2) . . ?
O3 C21 C23 101.5(2) . . ?
O3 C21 C24 109.1(2) . . ?
C22 C21 C23 110.5(3) . . ?
C24 C21 C22 114.7(3) . . ?
C24 C21 C23 110.9(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
