# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1588886'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-05-22 downloaded from the CCDC.
;
_audit_creation_date             2016-06-02
_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 N3 O2'
_chemical_formula_sum            'C20 H17 N3 O2'
_chemical_formula_weight         331.36
_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                   9.949(2)
_cell_length_b                   15.604(3)
_cell_length_c                   11.098(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.703(4)
_cell_angle_gamma                90
_cell_volume                     1666.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4092
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             696
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16743
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         3.181
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9652
	          2theta: -15.0904
scan:
	Number of images: 300
	           Slice: -105.0000 - 45.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9652
	          2theta: -15.0904
scan:
	Number of images: 200
	           Slice: -105.0000 - -5.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9652
	          2theta: -15.0904
;
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.068166
_diffrn_orient_matrix_UB_12      -0.069782
_diffrn_orient_matrix_UB_13      -0.035805
_diffrn_orient_matrix_UB_21      0.002239
_diffrn_orient_matrix_UB_22      0.027494
_diffrn_orient_matrix_UB_23      -0.057847
_diffrn_orient_matrix_UB_31      0.052425
_diffrn_orient_matrix_UB_32      -0.070313
_diffrn_orient_matrix_UB_33      -0.031390
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3135
_reflns_number_total             3778
_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-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.044
_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)+(0.0514P)²+0.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.17268(10) 0.38681(6) 0.43716(8) 0.0260(2) Uani 1 1 d . . . . .
O2 O 0.36672(9) 0.08763(6) 0.38568(8) 0.0244(2) Uani 1 1 d . . . . .
N1 N 0.21455(11) 0.39857(7) 0.64765(10) 0.0215(2) Uani 1 1 d . . . . .
H1 H 0.2530(16) 0.3749(10) 0.7194(15) 0.026 Uiso 1 1 d R . . . .
N2 N 0.35660(10) 0.24993(7) 0.68011(9) 0.0203(2) Uani 1 1 d . . . . .
N3 N -0.18742(12) 0.12803(7) -0.58022(10) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.15207(14) 0.48278(8) 0.64627(12) 0.0253(3) Uani 1 1 d . . . . .
H1A H 0.1632 0.5149 0.5735 0.038 Uiso 1 1 calc GR . . . .
H1B H 0.1979 0.5138 0.7224 0.038 Uiso 1 1 calc GR . . . .
H1C H 0.0529 0.4765 0.6419 0.038 Uiso 1 1 calc GR . . . .
C2 C 0.22110(12) 0.35852(7) 0.54315(10) 0.0182(2) Uani 1 1 d . . . . .
C3 C 0.29448(12) 0.27263(7) 0.56254(10) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.29284(12) 0.22287(7) 0.45861(10) 0.0177(2) Uani 1 1 d . . . . .
H4 H 0.2485 0.2422 0.3770 0.021 Uiso 1 1 calc R . . . .
C5 C 0.35849(12) 0.14368(7) 0.47844(10) 0.0184(2) Uani 1 1 d . . . . .
C6 C 0.42344(12) 0.11804(8) 0.59944(11) 0.0204(2) Uani 1 1 d . . . . .
H6 H 0.4683 0.0640 0.6153 0.025 Uiso 1 1 calc R . . . .
C7 C 0.42066(12) 0.17358(8) 0.69583(11) 0.0212(3) Uani 1 1 d . . . . .
H7 H 0.4669 0.1567 0.7781 0.025 Uiso 1 1 calc R . . . .
C8 C 0.29758(13) 0.10941(8) 0.26259(11) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.15988(13) 0.08638(8) 0.21656(11) 0.0231(3) Uani 1 1 d . . . . .
H9 H 0.1096 0.0608 0.2694 0.028 Uiso 1 1 calc R . . . .
C10 C 0.09617(13) 0.10124(8) 0.09156(12) 0.0236(3) Uani 1 1 d . . . . .
H10 H 0.0017 0.0855 0.0588 0.028 Uiso 1 1 calc R . . . .
C11 C 0.16986(13) 0.13919(8) 0.01331(11) 0.0220(3) Uani 1 1 d . . . . .
C12 C 0.30778(14) 0.16302(8) 0.06412(11) 0.0247(3) Uani 1 1 d . . . . .
H12 H 0.3585 0.1896 0.0124 0.030 Uiso 1 1 calc R . . . .
C13 C 0.37232(14) 0.14859(8) 0.18875(12) 0.0247(3) Uani 1 1 d . . . . .
H13 H 0.4661 0.1653 0.2226 0.030 Uiso 1 1 calc R . . . .
C14 C 0.11049(13) 0.14998(8) -0.12143(11) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.1677 0.1763 -0.1676 0.027 Uiso 1 1 calc R . . . .
C15 C -0.01650(13) 0.12602(8) -0.18435(11) 0.0232(3) Uani 1 1 d . . . . .
H15 H -0.0772 0.1053 -0.1372 0.028 Uiso 1 1 calc R . . . .
C16 C -0.07081(13) 0.12886(8) -0.32051(11) 0.0217(3) Uani 1 1 d . . . . .
C17 C -0.21196(13) 0.11440(9) -0.37136(11) 0.0251(3) Uani 1 1 d . . . . .
H17 H -0.2720 0.1049 -0.3184 0.030 Uiso 1 1 calc R . . . .
C18 C -0.26444(14) 0.11399(9) -0.49936(12) 0.0274(3) Uani 1 1 d . . . . .
H18 H -0.3608 0.1031 -0.5317 0.033 Uiso 1 1 calc R . . . .
C19 C -0.05173(14) 0.14257(9) -0.53093(12) 0.0279(3) Uani 1 1 d . . . . .
H19 H 0.0051 0.1534 -0.5864 0.034 Uiso 1 1 calc R . . . .
C20 C 0.01088(13) 0.14277(9) -0.40423(12) 0.0258(3) Uani 1 1 d . . . . .
H20 H 0.1080 0.1522 -0.3747 0.031 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 C2 1.2341(14) . ?
O2 C5 1.3690(14) . ?
O2 C8 1.4064(14) . ?
N1 H1 0.873(16) . ?
N1 C1 1.4521(16) . ?
N1 C2 1.3334(15) . ?
N2 C3 1.3418(14) . ?
N2 C7 1.3415(16) . ?
N3 C18 1.3378(17) . ?
N3 C19 1.3410(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5152(16) . ?
C3 C4 1.3871(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3888(16) . ?
C5 C6 1.3930(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3825(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3826(18) . ?
C8 C13 1.3812(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3906(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.4020(19) . ?
C11 C12 1.3951(18) . ?
C11 C14 1.4714(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3875(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.3326(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.4708(16) . ?
C16 C17 1.3926(18) . ?
C16 C20 1.3980(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3835(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.3859(17) . ?
C20 H20 0.9500 . ?

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
C5 O2 C8 117.92(9) . . ?
C1 N1 H1 118.7(10) . . ?
C2 N1 H1 119.2(10) . . ?
C2 N1 C1 122.02(10) . . ?
C7 N2 C3 116.56(10) . . ?
C18 N3 C19 116.28(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 124.61(11) . . ?
O1 C2 C3 120.61(10) . . ?
N1 C2 C3 114.78(10) . . ?
N2 C3 C2 117.26(10) . . ?
N2 C3 C4 124.48(11) . . ?
C4 C3 C2 118.26(10) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.42(10) . . ?
C5 C4 H4 121.3 . . ?
O2 C5 C4 124.38(10) . . ?
O2 C5 C6 116.09(10) . . ?
C4 C5 C6 119.52(10) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 C5 118.06(11) . . ?
C7 C6 H6 121.0 . . ?
N2 C7 C6 123.94(11) . . ?
N2 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C9 C8 O2 119.38(11) . . ?
C13 C8 O2 118.63(11) . . ?
C13 C8 C9 121.86(11) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.90(12) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.72(12) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 122.66(11) . . ?
C12 C11 C10 118.52(11) . . ?
C12 C11 C14 118.70(11) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.24(12) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C12 118.73(12) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C11 C14 H14 117.2 . . ?
C15 C14 C11 125.67(12) . . ?
C15 C14 H14 117.2 . . ?
C14 C15 H15 117.2 . . ?
C14 C15 C16 125.60(12) . . ?
C16 C15 H15 117.2 . . ?
C17 C16 C15 118.77(11) . . ?
C17 C16 C20 116.90(11) . . ?
C20 C16 C15 124.31(11) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.72(12) . . ?
C18 C17 H17 120.1 . . ?
N3 C18 C17 123.84(12) . . ?
N3 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
N3 C19 H19 117.9 . . ?
N3 C19 C20 124.12(12) . . ?
C20 C19 H19 117.9 . . ?
C16 C20 H20 120.4 . . ?
C19 C20 C16 119.12(12) . . ?
C19 C20 H20 120.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N3 0.873(16) 2.152(16) 2.9580(16) 153.3(14) 4_667

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 C2 C3 N2 173.45(11) . . . . ?
O1 C2 C3 C4 -6.71(17) . . . . ?
O2 C5 C6 C7 178.45(11) . . . . ?
O2 C8 C9 C10 -174.21(10) . . . . ?
O2 C8 C13 C12 174.17(11) . . . . ?
N1 C2 C3 N2 -6.53(15) . . . . ?
N1 C2 C3 C4 173.30(11) . . . . ?
N2 C3 C4 C5 0.96(18) . . . . ?
N3 C19 C20 C16 -1.4(2) . . . . ?
C1 N1 C2 O1 -2.12(19) . . . . ?
C1 N1 C2 C3 177.87(11) . . . . ?
C2 C3 C4 C5 -178.86(10) . . . . ?
C3 N2 C7 C6 -1.20(18) . . . . ?
C3 C4 C5 O2 -179.49(11) . . . . ?
C3 C4 C5 C6 -0.62(17) . . . . ?
C4 C5 C6 C7 -0.51(17) . . . . ?
C5 O2 C8 C9 -87.87(14) . . . . ?
C5 O2 C8 C13 96.15(13) . . . . ?
C5 C6 C7 N2 1.50(19) . . . . ?
C7 N2 C3 C2 179.75(10) . . . . ?
C7 N2 C3 C4 -0.07(17) . . . . ?
C8 O2 C5 C4 -3.72(17) . . . . ?
C8 O2 C5 C6 177.38(11) . . . . ?
C8 C9 C10 C11 -0.21(18) . . . . ?
C9 C8 C13 C12 -1.71(18) . . . . ?
C9 C10 C11 C12 -1.07(18) . . . . ?
C9 C10 C11 C14 175.04(11) . . . . ?
C10 C11 C12 C13 0.99(19) . . . . ?
C10 C11 C14 C15 0.1(2) . . . . ?
C11 C12 C13 C8 0.36(19) . . . . ?
C11 C14 C15 C16 -173.47(11) . . . . ?
C12 C11 C14 C15 176.16(13) . . . . ?
C13 C8 C9 C10 1.64(18) . . . . ?
C14 C11 C12 C13 -175.28(11) . . . . ?
C14 C15 C16 C17 -170.10(13) . . . . ?
C14 C15 C16 C20 11.9(2) . . . . ?
C15 C16 C17 C18 -177.89(12) . . . . ?
C15 C16 C20 C19 178.86(12) . . . . ?
C16 C17 C18 N3 -1.0(2) . . . . ?
C17 C16 C20 C19 0.81(19) . . . . ?
C18 N3 C19 C20 0.8(2) . . . . ?
C19 N3 C18 C17 0.4(2) . . . . ?
C20 C16 C17 C18 0.28(19) . . . . ?

_shelx_SHELXL_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1588889'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-05-22 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N3 O2'
_chemical_formula_weight         393.43
_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'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_cell_length_a                   5.4568(7)
_cell_length_b                   7.5939(5)
_cell_length_c                   45.622(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1890.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4680
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.2
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            15563
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_number_gt                3811
_reflns_number_total             3864
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(9)
_refine_ls_extinction_coef       0.0151(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0389P)²+0.4111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0743
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
H1 H 0.9897(19) 0.890(2) 0.3176(3) 0.023 Uiso 1 1 d D . .
H2 H 0.5159 0.8146 0.3654 0.024 Uiso 1 1 calc R . .
H3 H 0.5290 0.8520 0.4165 0.027 Uiso 1 1 calc R . .
H4 H 0.8611 0.9947 0.4384 0.027 Uiso 1 1 calc R . .
H5 H 1.1844 1.0965 0.4094 0.025 Uiso 1 1 calc R . .
H6 H 1.1735 1.0609 0.3584 0.022 Uiso 1 1 calc R . .
H9 H 0.3949 0.9636 0.2597 0.019 Uiso 1 1 calc R . .
H11 H 0.8793 0.7565 0.2013 0.021 Uiso 1 1 calc R . .
H12 H 1.1304 0.6870 0.2407 0.022 Uiso 1 1 calc R . .
H14 H 0.8404 1.0810 0.1820 0.022 Uiso 1 1 calc R . .
H15 H 0.9479 1.0940 0.1324 0.021 Uiso 1 1 calc R . .
H17 H 0.3406 0.8139 0.1113 0.023 Uiso 1 1 calc R . .
H18 H 0.2366 0.7956 0.1610 0.023 Uiso 1 1 calc R . .
H19 H 0.6034 0.9047 0.0722 0.023 Uiso 1 1 calc R . .
H20 H 1.0355 1.0809 0.0856 0.025 Uiso 1 1 calc R . .
H22 H 1.3020 1.1472 0.0431 0.029 Uiso 1 1 calc R . .
H23 H 1.3845 1.1270 -0.0074 0.032 Uiso 1 1 calc R . .
H24 H 1.1067 0.9752 -0.0376 0.032 Uiso 1 1 calc R . .
H25 H 0.7620 0.8482 -0.0165 0.033 Uiso 1 1 calc R . .
C1 C 0.8436(2) 0.93431(15) 0.35724(2) 0.0167(2) Uani 1 1 d . . .
C2 C 0.6515(2) 0.87204(17) 0.37431(3) 0.0201(2) Uani 1 1 d . . .
C3 C 0.6596(2) 0.89462(18) 0.40467(3) 0.0228(3) Uani 1 1 d . . .
C4 C 0.8570(2) 0.97881(17) 0.41774(2) 0.0223(3) Uani 1 1 d . . .
C5 C 1.0483(2) 1.03973(16) 0.40046(3) 0.0209(3) Uani 1 1 d . . .
C6 C 1.0426(2) 1.01836(16) 0.37016(2) 0.0187(2) Uani 1 1 d . . .
C7 C 0.6477(2) 0.90551(15) 0.30852(2) 0.0174(2) Uani 1 1 d . . .
C8 C 0.7096(2) 0.86147(15) 0.27709(2) 0.0157(2) Uani 1 1 d . . .
C9 C 0.5471(2) 0.90924(15) 0.25515(2) 0.0158(2) Uani 1 1 d . . .
C10 C 0.6142(2) 0.87490(15) 0.22618(2) 0.0163(2) Uani 1 1 d . . .
C11 C 0.8325(2) 0.78725(16) 0.22068(2) 0.0175(2) Uani 1 1 d . . .
C12 C 0.9802(2) 0.74592(15) 0.24450(2) 0.0182(2) Uani 1 1 d . . .
C13 C 0.5301(2) 0.93462(15) 0.17574(2) 0.0171(2) Uani 1 1 d . . .
C14 C 0.7409(2) 1.02545(16) 0.16765(2) 0.0187(2) Uani 1 1 d . . .
C15 C 0.8032(2) 1.03345(15) 0.13814(2) 0.0178(2) Uani 1 1 d . . .
C16 C 0.6566(2) 0.95392(15) 0.11655(2) 0.0173(2) Uani 1 1 d . . .
C17 C 0.4440(2) 0.86684(16) 0.12560(2) 0.0192(2) Uani 1 1 d . . .
C18 C 0.3808(2) 0.85616(16) 0.15514(2) 0.0189(2) Uani 1 1 d . . .
C19 C 0.7191(2) 0.95607(16) 0.08523(2) 0.0195(2) Uani 1 1 d . . .
C20 C 0.9216(2) 1.02269(16) 0.07314(2) 0.0206(3) Uani 1 1 d . . .
C21 C 0.9786(2) 1.01116(16) 0.04162(3) 0.0200(3) Uani 1 1 d . . .
C22 C 1.1917(2) 1.08734(18) 0.03046(3) 0.0239(3) Uani 1 1 d . . .
C23 C 1.2412(3) 1.07491(19) 0.00066(3) 0.0263(3) Uani 1 1 d . . .
C24 C 1.0784(3) 0.98559(18) -0.01708(3) 0.0265(3) Uani 1 1 d . . .
C25 C 0.8721(3) 0.91134(19) -0.00423(3) 0.0272(3) Uani 1 1 d . . .
N1 N 0.84670(19) 0.90769(14) 0.32643(2) 0.0191(2) Uani 1 1 d D . .
N2 N 0.92656(19) 0.78302(13) 0.27240(2) 0.0175(2) Uani 1 1 d . . .
N3 N 0.8192(2) 0.92334(15) 0.02433(2) 0.0246(2) Uani 1 1 d . . .
O1 O 0.43725(16) 0.93950(12) 0.316073(18) 0.02204(19) Uani 1 1 d . . .
O2 O 0.45227(15) 0.92713(12) 0.204989(16) 0.02062(19) 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 C2 1.3892(17) . ?
C1 C6 1.3904(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3962(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3872(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3877(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3923(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.5107(15) . ?
C8 C9 1.3855(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3963(15) . ?
C10 C11 1.3871(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3890(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3909(17) . ?
C13 C18 1.3794(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3901(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.4050(16) . ?
C16 C17 1.3979(17) . ?
C16 C19 1.4692(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.3936(16) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.3344(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.4740(15) . ?
C21 C22 1.3950(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3890(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.3799(19) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(2) . ?
C25 H25 0.9500 . ?
N1 H1 0.888(9) . ?
N1 C1 1.4198(14) . ?
N1 C7 1.3593(15) . ?
N2 C8 1.3425(16) . ?
N2 C12 1.3362(15) . ?
N3 C21 1.3505(16) . ?
N3 C25 1.3376(16) . ?
O1 C7 1.2264(15) . ?
O2 C10 1.3685(14) . ?
O2 C13 1.4016(13) . ?

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
C2 C1 C6 120.52(10) . . ?
C2 C1 N1 121.02(11) . . ?
C6 C1 N1 118.41(10) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.38(12) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.50(12) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.58(11) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.54(12) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.3 . . ?
C1 C6 C5 119.48(11) . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C8 113.25(10) . . ?
O1 C7 C8 121.52(10) . . ?
O1 C7 N1 125.21(10) . . ?
C9 C8 C7 118.97(10) . . ?
N2 C8 C7 116.54(10) . . ?
N2 C8 C9 124.44(10) . . ?
C8 C9 H9 121.1 . . ?
C8 C9 C10 117.84(11) . . ?
C10 C9 H9 121.1 . . ?
C11 C10 C9 119.09(10) . . ?
O2 C10 C9 116.44(10) . . ?
O2 C10 C11 124.44(10) . . ?
C10 C11 H11 121.1 . . ?
C10 C11 C12 117.72(11) . . ?
C12 C11 H11 121.1 . . ?
C11 C12 H12 117.6 . . ?
N2 C12 H12 117.6 . . ?
N2 C12 C11 124.79(11) . . ?
C14 C13 O2 121.55(10) . . ?
C18 C13 C14 121.47(10) . . ?
C18 C13 O2 116.88(11) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C15 C14 C13 118.74(10) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.39(11) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C19 123.00(11) . . ?
C17 C16 C15 117.97(10) . . ?
C17 C16 C19 119.02(10) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C18 C17 C16 121.23(11) . . ?
C13 C18 H18 120.4 . . ?
C13 C18 C17 119.18(11) . . ?
C17 C18 H18 120.4 . . ?
C16 C19 H19 116.6 . . ?
C20 C19 H19 116.6 . . ?
C20 C19 C16 126.77(11) . . ?
C19 C20 H20 118.1 . . ?
C19 C20 C21 123.76(11) . . ?
C21 C20 H20 118.1 . . ?
C22 C21 C20 120.50(11) . . ?
N3 C21 C20 117.59(11) . . ?
N3 C21 C22 121.91(11) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C23 C22 C21 119.39(12) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C24 C23 C22 118.84(12) . . ?
C23 C24 H24 120.9 . . ?
C23 C24 C25 118.28(11) . . ?
C25 C24 H24 120.9 . . ?
C24 C25 H25 118.0 . . ?
N3 C25 H25 118.0 . . ?
N3 C25 C24 123.95(13) . . ?
C1 N1 H1 118.7(10) . . ?
C7 N1 H1 115.3(10) . . ?
C7 N1 C1 125.98(10) . . ?
C12 N2 C8 116.02(10) . . ?
C25 N3 C21 117.61(11) . . ?
C10 O2 C13 119.25(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.888(9) 2.472(11) 3.2659(14) 149.2(13) 1_655

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
C1 C2 C3 C4 0.18(19) . . . . ?
C1 N1 C7 C8 -175.98(10) . . . . ?
C1 N1 C7 O1 5.8(2) . . . . ?
C2 C1 C6 C5 0.07(17) . . . . ?
C2 C3 C4 C5 -0.47(19) . . . . ?
C3 C4 C5 C6 0.56(18) . . . . ?
C4 C5 C6 C1 -0.37(18) . . . . ?
C6 C1 C2 C3 0.02(18) . . . . ?
C7 C8 C9 C10 176.87(10) . . . . ?
C7 N1 C1 C2 34.32(18) . . . . ?
C7 N1 C1 C6 -148.17(12) . . . . ?
C8 C9 C10 C11 3.26(16) . . . . ?
C8 C9 C10 O2 -178.61(10) . . . . ?
C8 N2 C12 C11 1.98(17) . . . . ?
C9 C10 C11 C12 -3.28(17) . . . . ?
C10 C11 C12 N2 0.63(18) . . . . ?
C10 O2 C13 C14 -51.92(15) . . . . ?
C10 O2 C13 C18 131.61(12) . . . . ?
C12 N2 C8 C7 -179.50(10) . . . . ?
C12 N2 C8 C9 -2.00(16) . . . . ?
C13 C14 C15 C16 0.78(17) . . . . ?
C13 O2 C10 C9 165.33(10) . . . . ?
C13 O2 C10 C11 -16.65(17) . . . . ?
C14 C13 C18 C17 0.62(18) . . . . ?
C14 C15 C16 C17 0.41(17) . . . . ?
C14 C15 C16 C19 -178.58(11) . . . . ?
C15 C16 C17 C18 -1.12(17) . . . . ?
C15 C16 C19 C20 3.61(19) . . . . ?
C16 C17 C18 C13 0.63(18) . . . . ?
C16 C19 C20 C21 176.38(11) . . . . ?
C17 C16 C19 C20 -175.37(12) . . . . ?
C18 C13 C14 C15 -1.31(18) . . . . ?
C19 C16 C17 C18 177.91(11) . . . . ?
C19 C20 C21 C22 178.63(12) . . . . ?
C19 C20 C21 N3 -2.03(18) . . . . ?
C20 C21 C22 C23 -179.90(12) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C21 N3 C25 C24 -0.9(2) . . . . ?
C22 C23 C24 C25 -0.2(2) . . . . ?
C23 C24 C25 N3 1.1(2) . . . . ?
C25 N3 C21 C20 -179.35(12) . . . . ?
C25 N3 C21 C22 -0.02(19) . . . . ?
N1 C1 C2 C3 177.48(11) . . . . ?
N1 C1 C6 C5 -177.46(11) . . . . ?
N1 C7 C8 C9 -159.18(11) . . . . ?
N1 C7 C8 N2 18.47(15) . . . . ?
N2 C8 C9 C10 -0.58(17) . . . . ?
N3 C21 C22 C23 0.80(19) . . . . ?
O1 C7 C8 C9 19.09(17) . . . . ?
O1 C7 C8 N2 -163.26(11) . . . . ?
O2 C10 C11 C12 178.75(11) . . . . ?
O2 C13 C14 C15 -177.62(10) . . . . ?
O2 C13 C18 C17 177.09(10) . . . . ?

