# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_7269
_audit_block_doi                 10.5517/ccdc.csd.cc23ld37
_database_code_depnum_ccdc_archive 'CCDC 1954088'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;
_audit_creation_date             2019-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.30
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                   9.5333(7)
_cell_length_b                   10.8109(10)
_cell_length_c                   14.0387(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.958(9)
_cell_angle_gamma                90
_cell_volume                     1397.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1474
_cell_measurement_theta_max      26.6760
_cell_measurement_theta_min      4.4160
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53280
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_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    1.1607
_exptl_crystal_F_000             520.2433
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6908
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.52
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.9955
_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      -0.0333986000
_diffrn_orient_matrix_UB_12      0.0453558000
_diffrn_orient_matrix_UB_13      -0.0350066000
_diffrn_orient_matrix_UB_21      0.0057377000
_diffrn_orient_matrix_UB_22      0.0437164000
_diffrn_orient_matrix_UB_23      0.0384802000
_diffrn_orient_matrix_UB_31      0.0691711000
_diffrn_orient_matrix_UB_32      0.0183353000
_diffrn_orient_matrix_UB_33      -0.0051311000
_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              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1673
_reflns_number_total             2450
_reflns_odcompleteness_completeness 99.11
_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         0.2204
_refine_diff_density_min         -0.2384
_refine_diff_density_rms         0.0518
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7819
_refine_ls_goodness_of_fit_ref   0.9701
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      0.9701
_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          0.1321
_refine_ls_wR_factor_ref         0.1569
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00h)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00g), C00G(H00j), C00F(H00i), C00B(H00c)
2.c X=CH2 refined with riding coordinates:
 N003(H00a,H00b)
2.d Idealised Me refined as rotating group:
 C00C(H00d,H00e,H00f), C00H(H00k,H00l,H00m), C00I(H00n,H00o,H00p)
;
_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 0.21680(12) 0.37245(12) 0.75224(9) 0.0573(4) Uani 1.000000 .
O002 O 0.08402(13) 0.44580(15) 0.60753(11) 0.0735(5) Uani 1.000000 .
N003 N 0.22300(18) 0.60042(16) 0.51057(12) 0.0687(5) Uani 1.000000 .
N004 N 0.2795(2) 0.67657(19) 0.87271(13) 0.0704(6) Uani 1.000000 .
C005 C 0.33173(17) 0.50373(17) 0.66520(12) 0.0454(5) Uani 1.000000 .
C006 C 0.33620(19) 0.58022(17) 0.58756(13) 0.0492(5) Uani 1.000000 .
C007 C 0.46563(18) 0.48392(17) 0.74682(13) 0.0450(5) Uani 1.000000 .
C008 C 0.48273(19) 0.53925(16) 0.83843(13) 0.0476(5) Uani 1.000000 .
C009 C 0.3682(2) 0.61554(19) 0.85613(13) 0.0521(5) Uani 1.000000 .
C00A C 0.19970(19) 0.44106(17) 0.66938(14) 0.0515(5) Uani 1.000000 .
C00B C 0.6085(2) 0.5216(2) 0.91395(14) 0.0600(6) Uani 1.000000 .
C00C C 0.4726(2) 0.6472(2) 0.58408(15) 0.0604(6) Uani 1.000000 .
C00D C 0.5774(2) 0.4091(2) 0.73427(15) 0.0590(5) Uani 1.000000 .
C00E C 0.0941(2) 0.2992(2) 0.76397(16) 0.0629(6) Uani 1.000000 .
C00F C 0.7170(2) 0.4469(2) 0.89890(16) 0.0693(7) Uani 1.000000 .
C00G C 0.7015(2) 0.3900(2) 0.80907(17) 0.0684(6) Uani 1.000000 .
C00H C 0.1092(3) 0.2927(3) 0.8730(2) 0.0986(10) Uani 1.000000 .
C00I C 0.0988(3) 0.1750(2) 0.7167(3) 0.1058(10) Uani 1.000000 .
H00g H 0.5686(2) 0.3707(2) 0.67374(15) 0.0708(7) Uiso 1.000000 R
H00j H 0.7746(2) 0.3388(2) 0.79880(17) 0.0821(7) Uiso 1.000000 R
H00i H 0.8009(2) 0.4347(2) 0.94926(16) 0.0832(8) Uiso 1.000000 R
H00c H 0.6188(2) 0.5604(2) 0.97450(14) 0.0720(7) Uiso 1.000000 R
H00a H 0.14133(18) 0.56472(16) 0.50749(12) 0.0824(6) Uiso 1.000000 R
H00b H 0.23167(18) 0.64913(16) 0.46400(12) 0.0824(6) Uiso 1.000000 R
H00d H 0.5352(7) 0.5921(4) 0.5605(10) 0.0906(9) Uiso 1.000000 GR
H00e H 0.4486(2) 0.7168(7) 0.5405(8) 0.0906(9) Uiso 1.000000 GR
H00f H 0.5213(8) 0.6754(11) 0.6490(2) 0.0906(9) Uiso 1.000000 GR
H00h H 0.0033(2) 0.3413(2) 0.73166(16) 0.0755(7) Uiso 1.000000 R
H00k H 0.2012(9) 0.2564(16) 0.9051(3) 0.1479(14) Uiso 1.000000 GR
H00l H 0.104(2) 0.3746(4) 0.8982(3) 0.1479(14) Uiso 1.000000 GR
H00m H 0.0323(12) 0.2429(15) 0.8853(2) 0.1479(14) Uiso 1.000000 GR
H00n H 0.082(2) 0.1853(3) 0.6468(3) 0.1587(15) Uiso 1.000000 GR
H00o H 0.1922(9) 0.1379(9) 0.7431(11) 0.1587(15) Uiso 1.000000 GR
H00p H 0.0247(16) 0.1227(7) 0.7300(14) 0.1587(15) 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 C00A 1.353(2) . ?
O001 C00E 1.456(2) . ?
O002 C00A 1.216(2) . ?
N003 C006 1.334(2) . ?
N003 H00a 0.8600 . ?
N003 H00b 0.8600 . ?
N004 C009 1.143(2) . ?
C005 C006 1.378(3) . ?
C005 C007 1.494(2) . ?
C005 C00A 1.444(2) . ?
C006 C00C 1.500(3) . ?
C007 C008 1.389(2) . ?
C007 C00D 1.385(3) . ?
C008 C009 1.440(3) . ?
C008 C00B 1.394(2) . ?
C00B C00F 1.371(3) . ?
C00B H00c 0.9300 . ?
C00C H00d 0.9600 . ?
C00C H00e 0.9600 . ?
C00C H00f 0.9600 . ?
C00D C00G 1.380(3) . ?
C00D H00g 0.9300 . ?
C00E C00H 1.502(3) . ?
C00E C00I 1.503(3) . ?
C00E H00h 0.9800 . ?
C00F C00G 1.376(3) . ?
C00F H00i 0.9300 . ?
C00G H00j 0.9300 . ?
C00H H00k 0.9600 . ?
C00H H00l 0.9600 . ?
C00H H00m 0.9600 . ?
C00I H00n 0.9600 . ?
C00I H00o 0.9600 . ?
C00I H00p 0.9600 . ?

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
C00E O001 C00A 118.24(14) . . ?
H00a N003 C006 120.0 . . ?
H00b N003 C006 120.0 . . ?
H00b N003 H00a 120.0 . . ?
C007 C005 C006 119.87(15) . . ?
C00A C005 C006 121.28(16) . . ?
C00A C005 C007 118.85(15) . . ?
C005 C006 N003 123.76(17) . . ?
C00C C006 N003 114.94(17) . . ?
C00C C006 C005 121.30(16) . . ?
C008 C007 C005 121.40(16) . . ?
C00D C007 C005 121.28(16) . . ?
C00D C007 C008 117.32(16) . . ?
C009 C008 C007 119.56(16) . . ?
C00B C008 C007 121.17(18) . . ?
C00B C008 C009 119.27(17) . . ?
C008 C009 N004 178.16(19) . . ?
O002 C00A O001 121.51(17) . . ?
C005 C00A O001 112.29(15) . . ?
C005 C00A O002 126.20(18) . . ?
C00F C00B C008 119.92(19) . . ?
H00c C00B C008 120.04(12) . . ?
H00c C00B C00F 120.04(12) . . ?
H00d C00C C006 109.5 . . ?
H00e C00C C006 109.5 . . ?
H00e C00C H00d 109.5 . . ?
H00f C00C C006 109.5 . . ?
H00f C00C H00d 109.5 . . ?
H00f C00C H00e 109.5 . . ?
C00G C00D C007 121.8(2) . . ?
H00g C00D C007 119.09(11) . . ?
H00g C00D C00G 119.09(14) . . ?
C00H C00E O001 105.81(17) . . ?
C00I C00E O001 108.64(18) . . ?
C00I C00E C00H 113.7(2) . . ?
H00h C00E O001 109.51(9) . . ?
H00h C00E C00H 109.51(13) . . ?
H00h C00E C00I 109.51(14) . . ?
C00G C00F C00B 119.82(19) . . ?
H00i C00F C00B 120.09(12) . . ?
H00i C00F C00G 120.09(12) . . ?
C00F C00G C00D 119.9(2) . . ?
H00j C00G C00D 120.03(14) . . ?
H00j C00G C00F 120.03(12) . . ?
H00k C00H C00E 109.5 . . ?
H00l C00H C00E 109.5 . . ?
H00l C00H H00k 109.5 . . ?
H00m C00H C00E 109.5 . . ?
H00m C00H H00k 109.5 . . ?
H00m C00H H00l 109.5 . . ?
H00n C00I C00E 109.5 . . ?
H00o C00I C00E 109.5 . . ?
H00o C00I H00n 109.5 . . ?
H00p C00I C00E 109.5 . . ?
H00p C00I H00n 109.5 . . ?
H00p C00I H00o 109.5 . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.754
_oxdiff_exptl_absorpt_empirical_full_min 0.841
_exptl_crystal_colour            white
