# 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_3993
_database_code_depnum_ccdc_archive 'CCDC 1828308'
_audit_update_record             
;
2018-03-08 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_audit_creation_date             2018-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H16 N2 O, C4 H4 O2'
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.0455(8)
_cell_length_b                   9.9480(9)
_cell_length_c                   11.7172(17)
_cell_angle_alpha                94.495(10)
_cell_angle_beta                 95.250(10)
_cell_angle_gamma                98.331(7)
_cell_volume                     1034.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0150
_cell_measurement_theta_min      3.3230
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7650
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.85
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  76.00   1.00    7.50    --   16.81  57.00 -30.00   77
  2  ω     52.00  88.00   1.00    7.50    --   16.81 178.00 120.00   36
  3  ω    -21.00  83.00   1.00    7.50    --   16.81  19.00 -90.00  104
  4  ω    -23.00  23.00   1.00    7.50    --  -17.43 -99.00-180.00   46
  5  ω    -24.00   3.00   1.00    7.50    --  -17.43 -99.00  60.00   27
  6  ω    -49.00  37.00   1.00    7.50    --   16.81 -77.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0164965000
_diffrn_orient_matrix_UB_12      -0.0721833000
_diffrn_orient_matrix_UB_13      -0.0030879000
_diffrn_orient_matrix_UB_21      0.0137256000
_diffrn_orient_matrix_UB_22      -0.0041187000
_diffrn_orient_matrix_UB_23      -0.0587159000
_diffrn_orient_matrix_UB_31      0.0767410000
_diffrn_orient_matrix_UB_32      -0.0032689000
_diffrn_orient_matrix_UB_33      0.0164482000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2657
_reflns_number_total             4214
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.1274
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1320P)²+3.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3304
_refine_ls_wR_factor_ref         0.3582
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C3(H3), C4(H4), C6(H6), C10(H10), C9(H9), C11(H11),
 C20(H20), C16(H16), C17(H17), C18(H18), C24(H24)
2.b Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.1713(4) 0.4826(4) 0.1444(4) 0.0371(10) Uani 1 d . . .
C15 C 0.4456(5) 0.7596(5) 0.1460(4) 0.0343(10) Uani 1 d . . .
N2 N 0.3954(5) 0.4231(4) 0.1190(4) 0.0387(10) Uani 1 d . . .
C7 C 0.3049(6) 0.3180(5) 0.1634(4) 0.0409(12) Uani 1 d . . .
C1 C 0.3095(5) 0.5182(5) 0.1098(4) 0.0350(11) Uani 1 d . . .
C14 C 0.3262(5) 0.6608(5) 0.0699(4) 0.0347(11) Uani 1 d . . .
C12 C 0.1082(6) 0.8089(6) 0.0639(5) 0.0459(13) Uani 1 d . . .
H12 H 0.1652 0.8825 0.0364 0.055 Uiso 1 calc . . R
C2 C 0.1633(6) 0.3538(5) 0.1804(4) 0.0405(12) Uani 1 d . . .
C13 C 0.1693(5) 0.6933(5) 0.0857(4) 0.0360(11) Uani 1 d . . .
C8 C 0.0828(5) 0.5866(5) 0.1295(4) 0.0366(11) Uani 1 d . . .
C5 C 0.2281(9) 0.1062(6) 0.2362(5) 0.0619(17) Uani 1 d . . .
H5 H 0.2478 0.0214 0.2563 0.074 Uiso 1 calc . . R
C3 C 0.0529(7) 0.2670(6) 0.2235(5) 0.0524(14) Uani 1 d . . .
H3 H -0.0408 0.2912 0.2338 0.063 Uiso 1 calc . . R
C4 C 0.0890(9) 0.1429(6) 0.2504(6) 0.0641(18) Uani 1 d . . .
H4 H 0.0173 0.0816 0.2792 0.077 Uiso 1 calc . . R
C6 C 0.3380(7) 0.1919(6) 0.1931(5) 0.0519(14) Uani 1 d . . .
H6 H 0.4315 0.1666 0.1840 0.062 Uiso 1 calc . . R
C10 C -0.1244(6) 0.7042(6) 0.1242(5) 0.0519(15) Uani 1 d . . .
H10 H -0.2238 0.7093 0.1359 0.062 Uiso 1 calc . . R
C9 C -0.0659(6) 0.5876(6) 0.1481(5) 0.0446(13) Uani 1 d . . .
H9 H -0.1233 0.5137 0.1751 0.053 Uiso 1 calc . . R
C11 C -0.0396(6) 0.8132(6) 0.0837(5) 0.0510(14) Uani 1 d . . .
H11 H -0.0822 0.8907 0.0694 0.061 Uiso 1 calc . . R
O1 O 0.3465(4) 0.6595(4) -0.0480(3) 0.0406(9) Uani 1 d . . .
H1 H 0.3715 0.7378 -0.0640 0.061 Uiso 1 calc . . GR
C20 C 0.4708(6) 0.7498(6) 0.2623(5) 0.0479(13) Uani 1 d . . .
H20 H 0.4193 0.6762 0.2938 0.057 Uiso 1 calc . . R
C16 C 0.5247(6) 0.8696(5) 0.1001(5) 0.0419(12) Uani 1 d . . .
H16 H 0.5097 0.8789 0.0217 0.050 Uiso 1 calc . . R
C17 C 0.6259(6) 0.9655(6) 0.1711(6) 0.0504(14) Uani 1 d . . .
H17 H 0.6791 1.0386 0.1401 0.061 Uiso 1 calc . . R
C18 C 0.6474(6) 0.9529(6) 0.2856(6) 0.0551(15) Uani 1 d . . .
H18 H 0.7155 1.0177 0.3325 0.066 Uiso 1 calc . . R
C19 C 0.5694(7) 0.8449(7) 0.3333(5) 0.0539(15) Uani 1 d . . .
C21 C 0.5947(10) 0.8306(10) 0.4610(6) 0.092(3) Uani 1 d . . .
H21A H 0.5107 0.8554 0.4979 0.138 Uiso 1 calc . . GR
H21B H 0.6847 0.8896 0.4935 0.138 Uiso 1 calc . . GR
H21C H 0.6047 0.7378 0.4727 0.138 Uiso 1 calc . . GR
O3 O -0.1755(8) 0.3270(8) 0.4543(6) 0.125(3) Uani 1 d . . .
O2 O -0.2778(9) 0.4721(8) 0.5601(6) 0.123(3) Uani 1 d . . .
C23 C -0.2655(10) 0.4151(10) 0.4689(7) 0.082(2) Uani 1 d . . .
C22 C -0.3574(10) 0.4321(12) 0.3626(8) 0.108(3) Uani 1 d . . .
H22A H -0.3334 0.5239 0.3426 0.162 Uiso 1 calc . . GR
H22B H -0.4618 0.4138 0.3742 0.162 Uiso 1 calc . . GR
H22C H -0.3369 0.3696 0.3015 0.162 Uiso 1 calc . . GR
C25 C -0.063(2) 0.1882(13) 0.5708(11) 0.177(7) Uani 1 d . . .
C24 C -0.0702(17) 0.3116(16) 0.5515(12) 0.178(7) Uani 1 d . . .
H24 H -0.0127 0.3856 0.5961 0.214 Uiso 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
N1 C1 1.356(6) . ?
N1 C2 1.374(6) . ?
N1 C8 1.409(6) . ?
C15 C14 1.519(7) . ?
C15 C20 1.374(7) . ?
C15 C16 1.391(7) . ?
N2 C7 1.396(7) . ?
N2 C1 1.313(6) . ?
C7 C2 1.405(7) . ?
C7 C6 1.394(7) . ?
C1 C14 1.520(7) . ?
C14 C13 1.526(6) . ?
C14 O1 1.410(6) . ?
C12 C13 1.377(7) . ?
C12 C11 1.384(8) . ?
C2 C3 1.382(8) . ?
C13 C8 1.386(7) . ?
C8 C9 1.383(7) . ?
C5 C4 1.381(10) . ?
C5 C6 1.372(9) . ?
C3 C4 1.374(9) . ?
C10 C9 1.381(8) . ?
C10 C11 1.377(9) . ?
C20 C19 1.371(8) . ?
C16 C17 1.386(8) . ?
C17 C18 1.356(9) . ?
C18 C19 1.382(9) . ?
C19 C21 1.514(9) . ?
O3 C23 1.292(11) . ?
O3 C24 1.449(11) . ?
O2 C23 1.192(10) . ?
C23 C22 1.468(11) . ?
C25 C24 1.276(16) . ?

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 N1 C2 108.2(4) . . ?
C1 N1 C8 110.9(4) . . ?
C2 N1 C8 140.8(4) . . ?
C20 C15 C14 121.7(5) . . ?
C20 C15 C16 118.1(5) . . ?
C16 C15 C14 120.0(4) . . ?
C1 N2 C7 103.7(4) . . ?
N2 C7 C2 111.1(4) . . ?
C6 C7 N2 129.4(5) . . ?
C6 C7 C2 119.5(5) . . ?
N1 C1 C14 110.9(4) . . ?
N2 C1 N1 113.4(4) . . ?
N2 C1 C14 135.7(4) . . ?
C15 C14 C1 112.1(4) . . ?
C15 C14 C13 111.2(4) . . ?
C1 C14 C13 99.2(4) . . ?
O1 C14 C15 113.2(4) . . ?
O1 C14 C1 111.9(4) . . ?
O1 C14 C13 108.4(4) . . ?
C13 C12 C11 118.7(6) . . ?
N1 C2 C7 103.6(4) . . ?
N1 C2 C3 134.0(5) . . ?
C3 C2 C7 122.4(5) . . ?
C12 C13 C14 129.5(5) . . ?
C12 C13 C8 119.3(5) . . ?
C8 C13 C14 111.1(4) . . ?
C13 C8 N1 107.9(4) . . ?
C9 C8 N1 129.1(5) . . ?
C9 C8 C13 123.0(5) . . ?
C6 C5 C4 121.5(6) . . ?
C4 C3 C2 116.4(6) . . ?
C3 C4 C5 122.3(6) . . ?
C5 C6 C7 117.9(6) . . ?
C11 C10 C9 121.9(5) . . ?
C10 C9 C8 116.3(5) . . ?
C10 C11 C12 120.8(5) . . ?
C19 C20 C15 122.1(5) . . ?
C17 C16 C15 120.1(5) . . ?
C18 C17 C16 120.2(6) . . ?
C17 C18 C19 120.8(6) . . ?
C20 C19 C18 118.6(6) . . ?
C20 C19 C21 120.7(6) . . ?
C18 C19 C21 120.7(6) . . ?
C23 O3 C24 117.4(9) . . ?
O3 C23 C22 113.0(8) . . ?
O2 C23 O3 123.6(9) . . ?
O2 C23 C22 123.4(10) . . ?
C25 C24 O3 114.5(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.574
