# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mx4584
_database_code_depnum_ccdc_archive 'CCDC 1494724'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_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 0.0033 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.596(4)
_cell_length_b                   5.5040(16)
_cell_length_c                   21.414(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.229(4)
_cell_angle_gamma                90
_cell_volume                     1461.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4286
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4818
_cell_measurement_theta_min      1.6428
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.65795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11253
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         1.752
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0484
	          2theta: -20.0255
scan:
	Number of images: 358
	           Slice: -110.0000 - 69.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0484
	          2theta: -20.0255
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3692
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0744
_diffrn_orient_matrix_UB_12      -0.0220
_diffrn_orient_matrix_UB_13      0.0222
_diffrn_orient_matrix_UB_21      -0.0101
_diffrn_orient_matrix_UB_22      0.1107
_diffrn_orient_matrix_UB_23      0.1437
_diffrn_orient_matrix_UB_31      -0.0101
_diffrn_orient_matrix_UB_32      -0.0371
_diffrn_orient_matrix_UB_33      0.0278
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3106
_reflns_number_total             3338
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.5778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1251
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.16710(8) 0.14597(19) 0.49725(5) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.29941(11) 0.4912(3) 0.45449(6) 0.0320(3) Uani 1 1 d . . . . .
C1 C 0.18512(11) 0.1374(3) 0.43512(6) 0.0267(3) Uani 1 1 d . . . . .
C2 C 0.13943(12) -0.0489(3) 0.39580(7) 0.0304(3) Uani 1 1 d . . . . .
H2 H 0.0966 -0.1647 0.4110 0.036 Uiso 1 1 calc R . . . .
C3 C 0.15750(13) -0.0631(3) 0.33375(7) 0.0338(3) Uani 1 1 d . . . . .
H3 H 0.1284 -0.1901 0.3075 0.041 Uiso 1 1 calc R . . . .
C4 C 0.21935(12) 0.1143(3) 0.31133(7) 0.0347(4) Uani 1 1 d . . . . .
H4 H 0.2302 0.1081 0.2695 0.042 Uiso 1 1 calc R . . . .
C5 C 0.26515(12) 0.3007(3) 0.35070(7) 0.0319(3) Uani 1 1 d . . . . .
H5 H 0.3063 0.4184 0.3349 0.038 Uiso 1 1 calc R . . . .
C6 C 0.25026(11) 0.3141(3) 0.41370(7) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.27979(11) 0.5104(3) 0.51903(6) 0.0279(3) Uani 1 1 d . . . . .
H7 H 0.2743 0.6834 0.5288 0.033 Uiso 1 1 calc R . . . .
C8 C 0.16888(12) 0.3914(3) 0.52125(6) 0.0273(3) Uani 1 1 d . . . . .
H8 H 0.1131 0.4850 0.4937 0.033 Uiso 1 1 calc R . . . .
C9 C 0.37001(11) 0.4022(3) 0.56779(6) 0.0268(3) Uani 1 1 d . . . . .
C10 C 0.39570(12) 0.5064(3) 0.62777(7) 0.0321(3) Uani 1 1 d . . . . .
H10 H 0.3606 0.6475 0.6367 0.039 Uiso 1 1 calc R . . . .
C11 C 0.47321(12) 0.4023(3) 0.67455(7) 0.0358(4) Uani 1 1 d . . . . .
H11 H 0.4897 0.4736 0.7145 0.043 Uiso 1 1 calc R . . . .
C12 C 0.52572(12) 0.1926(3) 0.66155(7) 0.0359(4) Uani 1 1 d . . . . .
H12 H 0.5771 0.1217 0.6928 0.043 Uiso 1 1 calc R . . . .
C13 C 0.50161(12) 0.0881(3) 0.60176(7) 0.0355(4) Uani 1 1 d . . . . .
H13 H 0.5373 -0.0521 0.5928 0.043 Uiso 1 1 calc R . . . .
C14 C 0.42406(12) 0.1928(3) 0.55512(7) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.4083 0.1220 0.5151 0.038 Uiso 1 1 calc R . . . .
C15 C 0.14104(11) 0.3855(3) 0.58667(7) 0.0272(3) Uani 1 1 d . . . . .
C16 C 0.08259(12) 0.5769(3) 0.60634(7) 0.0313(3) Uani 1 1 d . . . . .
H16 H 0.0581 0.7018 0.5782 0.038 Uiso 1 1 calc R . . . .
C17 C 0.06056(13) 0.5828(3) 0.66749(8) 0.0363(4) Uani 1 1 d . . . . .
H17 H 0.0209 0.7105 0.6801 0.044 Uiso 1 1 calc R . . . .
C18 C 0.09778(13) 0.3983(3) 0.70982(7) 0.0359(4) Uani 1 1 d . . . . .
H18 H 0.0844 0.4042 0.7511 0.043 Uiso 1 1 calc R . . . .
C19 C 0.15488(12) 0.2048(3) 0.69065(7) 0.0334(3) Uani 1 1 d . . . . .
H19 H 0.1787 0.0797 0.7188 0.040 Uiso 1 1 calc R . . . .
C20 C 0.17633(12) 0.1984(3) 0.62925(7) 0.0306(3) Uani 1 1 d . . . . .
H20 H 0.2145 0.0684 0.6164 0.037 Uiso 1 1 calc R . . . .
H1 H 0.3312(17) 0.603(4) 0.4392(9) 0.055(6) Uiso 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
O1 C1 1.3894(17) . ?
O1 C8 1.4444(18) . ?
N1 C6 1.3799(19) . ?
N1 C7 1.4504(19) . ?
N1 H1 0.83(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.551(2) . ?
C7 C9 1.5216(19) . ?
C8 H8 0.9800 . ?
C8 C15 1.504(2) . ?
C9 C10 1.391(2) . ?
C9 C14 1.390(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(2) . ?
C15 C20 1.395(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(2) . ?
C20 H20 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 O1 C8 112.20(11) . . ?
C6 N1 C7 121.43(13) . . ?
C6 N1 H1 117.8(14) . . ?
C7 N1 H1 119.7(14) . . ?
O1 C1 C6 119.63(13) . . ?
C2 C1 O1 119.10(13) . . ?
C2 C1 C6 121.26(13) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.12(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.28(14) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.59(14) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.90(14) . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C1 120.40(13) . . ?
N1 C6 C5 121.78(14) . . ?
C5 C6 C1 117.80(14) . . ?
N1 C7 H7 107.8 . . ?
N1 C7 C8 107.78(11) . . ?
N1 C7 C9 113.11(12) . . ?
C8 C7 H7 107.8 . . ?
C9 C7 H7 107.8 . . ?
C9 C7 C8 112.36(12) . . ?
O1 C8 C7 109.94(12) . . ?
O1 C8 H8 108.2 . . ?
O1 C8 C15 108.65(11) . . ?
C7 C8 H8 108.2 . . ?
C15 C8 C7 113.46(11) . . ?
C15 C8 H8 108.2 . . ?
C10 C9 C7 119.67(13) . . ?
C14 C9 C7 121.52(13) . . ?
C14 C9 C10 118.72(13) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.86(15) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.89(14) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.83(14) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.10(15) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.60(14) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C8 119.25(13) . . ?
C16 C15 C20 119.02(14) . . ?
C20 C15 C8 121.67(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.58(14) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.95(15) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.11(14) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.86(14) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.46(14) . . ?
C19 C20 H20 119.8 . . ?

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
O1 C1 C2 C3 -179.14(13) . . . . ?
O1 C1 C6 N1 2.2(2) . . . . ?
O1 C1 C6 C5 -179.18(12) . . . . ?
O1 C8 C15 C16 -145.76(13) . . . . ?
O1 C8 C15 C20 37.12(18) . . . . ?
N1 C7 C8 O1 54.72(14) . . . . ?
N1 C7 C8 C15 176.62(12) . . . . ?
N1 C7 C9 C10 146.23(14) . . . . ?
N1 C7 C9 C14 -37.25(19) . . . . ?
C1 O1 C8 C7 -59.25(14) . . . . ?
C1 O1 C8 C15 176.03(10) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C2 C1 C6 N1 -176.76(13) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 N1 176.78(14) . . . . ?
C4 C5 C6 C1 -1.8(2) . . . . ?
C6 N1 C7 C8 -23.85(18) . . . . ?
C6 N1 C7 C9 100.99(16) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C7 N1 C6 C1 -4.2(2) . . . . ?
C7 N1 C6 C5 177.25(13) . . . . ?
C7 C8 C15 C16 91.63(16) . . . . ?
C7 C8 C15 C20 -85.49(17) . . . . ?
C7 C9 C10 C11 175.97(14) . . . . ?
C7 C9 C14 C13 -175.91(14) . . . . ?
C8 O1 C1 C2 -150.39(13) . . . . ?
C8 O1 C1 C6 30.61(17) . . . . ?
C8 C7 C9 C10 -91.46(16) . . . . ?
C8 C7 C9 C14 85.06(17) . . . . ?
C8 C15 C16 C17 -176.62(14) . . . . ?
C8 C15 C20 C19 176.16(13) . . . . ?
C9 C7 C8 O1 -70.57(15) . . . . ?
C9 C7 C8 C15 51.33(17) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C9 C14 C13 0.6(2) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C14 C9 C10 C11 -0.7(2) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C15 C20 C19 -1.0(2) . . . . ?
C16 C17 C18 C19 -1.5(2) . . . . ?
C17 C18 C19 C20 1.1(2) . . . . ?
C18 C19 C20 C15 0.1(2) . . . . ?
C20 C15 C16 C17 0.6(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
