# 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_4924
_audit_block_doi                 10.5517/ccdc.csd.cc1zzt3w
_database_code_depnum_ccdc_archive 'CCDC 1846859'
_audit_update_record             
;
2018-06-02 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_audit_creation_date             2018-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C20 H18 N2 O'
_chemical_formula_sum            'C20 H18 N2 O'
_chemical_formula_weight         302.38
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.8905(12)
_cell_length_b                   13.8510(13)
_cell_length_c                   10.4548(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.114(10)
_cell_angle_gamma                90
_cell_volume                     1557.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1956
_cell_measurement_theta_max      27.4870
_cell_measurement_theta_min      3.9420
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22636
_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_density_diffrn    1.2897
_exptl_crystal_F_000             640.2630
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7527
_diffrn_reflns_theta_full        24.9918
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.79
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  84.00   1.00    3.41    --   15.81  38.00 -60.00   80
  2  ω    -19.00  54.00   1.00    3.41    --   15.81 -99.00 120.00   73
  3  ω     40.00  84.00   1.00    3.41    --   15.81 178.00 -90.00   44
  4  ω    -50.00 -22.00   1.00    3.41    --   15.81 -38.00 120.00   28
;
_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      -0.0543237000
_diffrn_orient_matrix_UB_12      -0.0273356000
_diffrn_orient_matrix_UB_13      -0.0220465000
_diffrn_orient_matrix_UB_21      0.0362030000
_diffrn_orient_matrix_UB_22      -0.0338312000
_diffrn_orient_matrix_UB_23      -0.0289374000
_diffrn_orient_matrix_UB_31      0.0095939000
_diffrn_orient_matrix_UB_32      -0.0271092000
_diffrn_orient_matrix_UB_33      0.0581749000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1993
_reflns_number_total             2733
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.3094
_refine_diff_density_min         -0.4034
_refine_diff_density_rms         0.1177
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             5.3765
_refine_ls_goodness_of_fit_ref   1.0272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.0272
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1519
_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 Secondary CH2 refined with riding coordinates:
 C00C(H00b,H00c)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00E(H00E), C00L(H00n), C00N(H00r), C00J(H00J), C00H(H00H),
 C00A(H00A)
2.c Idealised Me refined as rotating group:
 C00I(H00d,H00g,H00i), C00K(H00k,H00l,H00m), C00M(H00o,H00p,H00q)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O001 O 0.70256(14) 0.83149(10) 0.51121(15) 0.0671(5) Uani 1.000000 .
N002 N 0.66941(14) 0.52486(10) 0.71377(13) 0.0396(4) Uani 1.000000 .
N003 N 0.76347(13) 0.59743(10) 0.56093(13) 0.0407(4) Uani 1.000000 .
C004 C 0.53666(15) 0.62378(11) 0.55240(15) 0.0366(4) Uani 1.000000 .
C005 C 0.65737(17) 0.58421(11) 0.60316(15) 0.0354(4) Uani 1.000000 .
C006 C 0.51682(17) 0.68435(12) 0.44136(16) 0.0402(4) Uani 1.000000 .
C007 C 0.43708(16) 0.60121(12) 0.61749(17) 0.0414(5) Uani 1.000000 .
C008 C 0.56904(19) 0.50134(12) 0.77627(17) 0.0460(5) Uani 1.000000 .
C009 C 0.85026(17) 0.54704(12) 0.64574(16) 0.0416(5) Uani 1.000000 .
C00A C 0.45744(19) 0.53920(12) 0.72864(17) 0.0465(5) Uani 1.000000 .
C00B C 0.79608(17) 0.50098(12) 0.74168(16) 0.0416(5) Uani 1.000000 .
C00C C 0.61788(17) 0.70818(13) 0.36438(16) 0.0446(5) Uani 1.000000 .
C00D C 0.71870(18) 0.77563(13) 0.42632(18) 0.0469(5) Uani 1.000000 .
C00E C 0.31869(17) 0.63951(13) 0.57255(19) 0.0497(5) Uani 1.000000 .
C00F C 0.39832(18) 0.72000(13) 0.40272(18) 0.0478(5) Uani 1.000000 .
C00G C 0.29788(17) 0.69870(13) 0.4663(2) 0.0507(5) Uani 1.000000 .
C00H C 0.97847(19) 0.54102(14) 0.6463(2) 0.0547(5) Uani 1.000000 .
C00I C 0.8369(2) 0.77098(15) 0.3714(2) 0.0604(6) Uani 1.000000 .
C00J C 1.0482(2) 0.48774(16) 0.7415(2) 0.0645(6) Uani 1.000000 .
C00K C 0.5901(2) 0.43483(15) 0.88924(19) 0.0623(6) Uani 1.000000 .
C00L C 0.8677(2) 0.44872(15) 0.83923(19) 0.0613(6) Uani 1.000000 .
C00M C 0.1708(2) 0.73886(17) 0.4176(2) 0.0731(7) Uani 1.000000 .
C00N C 0.9929(2) 0.44282(17) 0.8364(2) 0.0695(7) Uani 1.000000 .
H00F H 0.38462(18) 0.76027(13) 0.33069(18) 0.0573(6) Uiso 1.000000 R
H00E H 0.25294(17) 0.62435(13) 0.61588(19) 0.0596(6) Uiso 1.000000 R
H00n H 0.8322(2) 0.41880(15) 0.90412(19) 0.0736(7) Uiso 1.000000 R
H00r H 1.0425(2) 0.40746(17) 0.9005(2) 0.0834(8) Uiso 1.000000 R
H00J H 1.1334(2) 0.48160(16) 0.7426(2) 0.0774(7) Uiso 1.000000 R
H00H H 1.01542(19) 0.57241(14) 0.5835(2) 0.0656(7) Uiso 1.000000 R
H00A H 0.39013(19) 0.52442(12) 0.76984(17) 0.0558(6) Uiso 1.000000 R
H00b H 0.65676(17) 0.64823(13) 0.34433(16) 0.0535(6) Uiso 1.000000 R
H00c H 0.57956(17) 0.73642(13) 0.28286(16) 0.0535(6) Uiso 1.000000 R
H00d H 0.8856(6) 0.8276(5) 0.3965(11) 0.0905(9) Uiso 1.000000 GR
H00g H 0.8828(6) 0.7146(6) 0.4036(11) 0.0905(9) Uiso 1.000000 GR
H00i H 0.8182(2) 0.7678(10) 0.2786(2) 0.0905(9) Uiso 1.000000 GR
H00k H 0.6281(14) 0.3764(5) 0.8653(5) 0.0934(9) Uiso 1.000000 GR
H00l H 0.6438(12) 0.4653(5) 0.9594(5) 0.0934(9) Uiso 1.000000 GR
H00m H 0.5119(3) 0.4199(9) 0.9160(10) 0.0934(9) Uiso 1.000000 GR
H00o H 0.1265(6) 0.6953(6) 0.3554(11) 0.1097(11) Uiso 1.000000 GR
H00p H 0.1259(5) 0.7466(10) 0.4889(3) 0.1097(11) Uiso 1.000000 GR
H00q H 0.1788(2) 0.8004(5) 0.3775(13) 0.1097(11) Uiso 1.000000 GR


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
O001 C00D 1.211(2) . ?
N002 C005 1.408(2) . ?
N002 C008 1.398(2) . ?
N002 C00B 1.404(2) . ?
N003 C005 1.313(2) . ?
N003 C009 1.379(2) . ?
C004 C005 1.445(2) . ?
C004 C006 1.421(2) . ?
C004 C007 1.404(2) . ?
C006 C00C 1.499(3) . ?
C006 C00F 1.381(3) . ?
C007 C00A 1.434(2) . ?
C007 C00E 1.404(3) . ?
C008 C00A 1.345(3) . ?
C008 C00K 1.487(2) . ?
C009 C00B 1.396(2) . ?
C009 C00H 1.398(3) . ?
C00A H00A 0.9300 . ?
C00B C00L 1.386(3) . ?
C00C C00D 1.507(2) . ?
C00C H00b 0.9700 . ?
C00C H00c 0.9700 . ?
C00D C00I 1.491(3) . ?
C00E C00G 1.371(3) . ?
C00E H00E 0.9300 . ?
C00F C00G 1.398(3) . ?
C00F H00F 0.9300 . ?
C00G C00M 1.504(3) . ?
C00H C00J 1.369(3) . ?
C00H H00H 0.9300 . ?
C00I H00d 0.9600 . ?
C00I H00g 0.9600 . ?
C00I H00i 0.9600 . ?
C00J C00N 1.387(3) . ?
C00J H00J 0.9300 . ?
C00K H00k 0.9600 . ?
C00K H00l 0.9600 . ?
C00K H00m 0.9600 . ?
C00L C00N 1.371(3) . ?
C00L H00n 0.9300 . ?
C00M H00o 0.9600 . ?
C00M H00p 0.9600 . ?
C00M H00q 0.9600 . ?
C00N H00r 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
C008 N002 C005 122.82(15) . . ?
C00B N002 C005 105.61(14) . . ?
C00B N002 C008 131.56(15) . . ?
C009 N003 C005 105.26(13) . . ?
C006 C004 C005 122.38(16) . . ?
C007 C004 C005 117.72(15) . . ?
C007 C004 C006 119.90(16) . . ?
N003 C005 N002 112.65(15) . . ?
C004 C005 N002 118.94(16) . . ?
C004 C005 N003 128.40(15) . . ?
C00C C006 C004 122.61(16) . . ?
C00F C006 C004 117.66(17) . . ?
C00F C006 C00C 119.71(16) . . ?
C00A C007 C004 119.61(17) . . ?
C00E C007 C004 119.50(17) . . ?
C00E C007 C00A 120.89(17) . . ?
C00A C008 N002 117.63(16) . . ?
C00K C008 N002 118.84(18) . . ?
C00K C008 C00A 123.51(18) . . ?
C00B C009 N003 111.63(16) . . ?
C00H C009 N003 127.97(17) . . ?
C00H C009 C00B 120.37(17) . . ?
C008 C00A C007 123.26(17) . . ?
H00A C00A C007 118.37(11) . . ?
H00A C00A C008 118.37(11) . . ?
C009 C00B N002 104.85(15) . . ?
C00L C00B N002 134.12(18) . . ?
C00L C00B C009 120.98(18) . . ?
C00D C00C C006 116.90(15) . . ?
H00b C00C C006 108.07(9) . . ?
H00b C00C C00D 108.07(10) . . ?
H00c C00C C006 108.07(9) . . ?
H00c C00C C00D 108.07(9) . . ?
H00c C00C H00b 107.3 . . ?
C00C C00D O001 122.03(19) . . ?
C00I C00D O001 122.96(18) . . ?
C00I C00D C00C 114.96(16) . . ?
C00G C00E C007 121.49(18) . . ?
H00E C00E C007 119.25(11) . . ?
H00E C00E C00G 119.25(11) . . ?
C00G C00F C006 123.42(18) . . ?
H00F C00F C006 118.29(11) . . ?
H00F C00F C00G 118.29(11) . . ?
C00F C00G C00E 118.03(18) . . ?
C00M C00G C00E 121.4(2) . . ?
C00M C00G C00F 120.6(2) . . ?
C00J C00H C009 118.3(2) . . ?
H00H C00H C009 120.86(11) . . ?
H00H C00H C00J 120.86(13) . . ?
H00d C00I C00D 109.5 . . ?
H00g C00I C00D 109.5 . . ?
H00g C00I H00d 109.5 . . ?
H00i C00I C00D 109.5 . . ?
H00i C00I H00d 109.5 . . ?
H00i C00I H00g 109.5 . . ?
C00N C00J C00H 120.6(2) . . ?
H00J C00J C00H 119.72(13) . . ?
H00J C00J C00N 119.72(14) . . ?
H00k C00K C008 109.5 . . ?
H00l C00K C008 109.5 . . ?
H00l C00K H00k 109.5 . . ?
H00m C00K C008 109.5 . . ?
H00m C00K H00k 109.5 . . ?
H00m C00K H00l 109.5 . . ?
C00N C00L C00B 117.5(2) . . ?
H00n C00L C00B 121.26(13) . . ?
H00n C00L C00N 121.26(13) . . ?
H00o C00M C00G 109.5 . . ?
H00p C00M C00G 109.5 . . ?
H00p C00M H00o 109.5 . . ?
H00q C00M C00G 109.5 . . ?
H00q C00M H00o 109.5 . . ?
H00q C00M H00p 109.5 . . ?
C00L C00N C00J 122.3(2) . . ?
H00r C00N C00J 118.84(14) . . ?
H00r C00N C00L 118.84(13) . . ?

_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 2.204
_oxdiff_exptl_absorpt_empirical_full_min 0.342
