# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_R2
_database_code_depnum_ccdc_archive 'CCDC 1868089'
loop_
_audit_author_name
_audit_author_address
'Maxime A. Siegler'
;Department of Chemistry, Johns Hopkins University
United States of America
;
_audit_update_record             
;
2018-09-17 deposited with the CCDC.	2019-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
2-[[4-[hydroxymethyl(methyl)amino]phenyl]methylene]propanedinitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.24645(14)
_cell_length_b                   17.8507(4)
_cell_length_c                   9.27013(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.1370(16)
_cell_angle_gamma                90
_cell_volume                     1198.30(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3821
_cell_measurement_theta_min      4.93
_cell_measurement_theta_max      71.97

_exptl_crystal_description       lath
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.730
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            7864
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.955
_diffrn_reflns_theta_max         71.868
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2347
_reflns_number_gt                1994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.2481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2347
_refine_ls_number_parameters     307
_refine_ls_number_restraints     728
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.2100(12) 0.0335(5) 0.0871(8) 0.0675(17) Uani 0.598(13) 1 d D U P A 1
C1 C 0.1822(13) -0.0106(5) 0.1721(9) 0.0373(14) Uani 0.598(13) 1 d D U P A 1
N2 N 0.0215(13) -0.1935(4) 0.1849(7) 0.0399(12) Uani 0.598(13) 1 d D U P A 1
C2 C 0.0797(14) -0.1366(4) 0.2249(8) 0.0300(12) Uani 0.598(13) 1 d D U P A 1
C3 C 0.1497(15) -0.0663(4) 0.2772(8) 0.0226(11) Uani 0.598(13) 1 d D U P A 1
C4 C 0.188(2) -0.0570(6) 0.4222(9) 0.0223(8) Uani 0.598(13) 1 d D U P A 1
H4 H 0.1639 -0.0995 0.4800 0.027 Uiso 0.598(13) 1 calc R U P A 1
C5 C 0.259(3) 0.0065(6) 0.5004(9) 0.0208(7) Uani 0.598(13) 1 d D U P A 1
C6 C 0.3010(19) 0.0765(5) 0.4383(8) 0.0226(8) Uani 0.598(13) 1 d D U P A 1
H6 H 0.2821 0.0829 0.3371 0.027 Uiso 0.598(13) 1 calc R U P A 1
C7 C 0.3682(10) 0.1355(4) 0.5191(7) 0.0231(8) Uani 0.598(13) 1 d D U P A 1
H7 H 0.3945 0.1817 0.4734 0.028 Uiso 0.598(13) 1 calc R U P A 1
C8 C 0.3987(10) 0.1281(4) 0.6701(7) 0.0266(8) Uani 0.598(13) 1 d D U P A 1
C9 C 0.3593(11) 0.0580(4) 0.7352(8) 0.0310(9) Uani 0.598(13) 1 d D U P A 1
H9 H 0.3792 0.0515 0.8363 0.037 Uiso 0.598(13) 1 calc R U P A 1
C10 C 0.2926(15) -0.0001(5) 0.6516(9) 0.0264(9) Uani 0.598(13) 1 d D U P A 1
H10 H 0.2680 -0.0466 0.6967 0.032 Uiso 0.598(13) 1 calc R U P A 1
N3 N 0.4611(8) 0.1821(2) 0.7704(4) 0.0346(12) Uani 0.531(3) 1 d D U P A 1
C11 C 0.4704(8) 0.1728(3) 0.9264(5) 0.0440(18) Uani 0.531(3) 1 d D U P A 1
H11A H 0.3487 0.1582 0.9596 0.066 Uiso 0.531(3) 1 calc R U P A 1
H11B H 0.5081 0.2202 0.9721 0.066 Uiso 0.531(3) 1 calc R U P A 1
H11C H 0.5606 0.1338 0.9526 0.066 Uiso 0.531(3) 1 calc R U P A 1
C12 C 0.5227(8) 0.2527(3) 0.7096(6) 0.0339(13) Uani 0.531(3) 1 d D U P A 1
H12A H 0.5891 0.2426 0.6203 0.041 Uiso 0.531(3) 1 calc R U P A 1
H12B H 0.6099 0.2775 0.7792 0.041 Uiso 0.531(3) 1 calc R U P A 1
C13 C 0.3604(9) 0.3053(3) 0.6749(6) 0.0356(11) Uani 0.531(3) 1 d D U P A 1
H13A H 0.4076 0.3533 0.6376 0.043 Uiso 0.531(3) 1 calc R U P A 1
H13B H 0.2790 0.2826 0.5987 0.043 Uiso 0.531(3) 1 calc R U P A 1
O1 O 0.2562(10) 0.3193(3) 0.8001(6) 0.0379(9) Uani 0.531(3) 1 d D U P A 1
H1 H 0.1808 0.2842 0.8111 0.057 Uiso 0.531(3) 1 calc R U P A 1
N1' N 0.1509(13) 0.0240(6) 0.0958(12) 0.0519(16) Uani 0.402(13) 1 d D U P A 2
C1' C 0.1473(18) -0.0207(7) 0.1867(14) 0.0353(18) Uani 0.402(13) 1 d D U P A 2
N2' N 0.0207(19) -0.2045(6) 0.2253(11) 0.0369(16) Uani 0.402(13) 1 d D U P A 2
C2' C 0.072(2) -0.1465(6) 0.2585(10) 0.0254(15) Uani 0.402(13) 1 d D U P A 2
C3' C 0.142(3) -0.0742(7) 0.3012(13) 0.0277(16) Uani 0.402(13) 1 d D U P A 2
C4' C 0.188(4) -0.0622(9) 0.4414(14) 0.0223(8) Uani 0.402(13) 1 d D U P A 2
H4' H 0.1736 -0.1049 0.5009 0.027 Uiso 0.402(13) 1 calc R U P A 2
C5' C 0.254(4) 0.0024(9) 0.5174(14) 0.0208(7) Uani 0.402(13) 1 d D U P A 2
C6' C 0.303(3) 0.0721(8) 0.4615(12) 0.0226(8) Uani 0.402(13) 1 d D U P A 2
H6' H 0.2916 0.0811 0.3606 0.027 Uiso 0.402(13) 1 calc R U P A 2
C7' C 0.3694(17) 0.1277(6) 0.5532(9) 0.0231(8) Uani 0.402(13) 1 d D U P A 2
H7' H 0.4040 0.1742 0.5125 0.028 Uiso 0.402(13) 1 calc R U P A 2
C8' C 0.3879(15) 0.1188(5) 0.7030(9) 0.0266(8) Uani 0.402(13) 1 d D U P A 2
C9' C 0.3311(17) 0.0506(6) 0.7563(12) 0.0310(9) Uani 0.402(13) 1 d D U P A 2
H9' H 0.3345 0.0428 0.8577 0.037 Uiso 0.402(13) 1 calc R U P A 2
C10' C 0.270(2) -0.0062(8) 0.6672(13) 0.0264(9) Uani 0.402(13) 1 d D U P A 2
H10' H 0.2376 -0.0529 0.7085 0.032 Uiso 0.402(13) 1 calc R U P A 2
N3' N 0.4813(14) 0.1908(5) 0.7354(8) 0.0272(14) Uani 0.2429(19) 1 d D U P A 2
C11' C 0.5079(18) 0.2622(6) 0.6590(9) 0.036(2) Uani 0.2429(19) 1 d D U P A 2
H11D H 0.4748 0.2557 0.5563 0.053 Uiso 0.2429(19) 1 calc R U P A 2
H11E H 0.4290 0.3008 0.6998 0.053 Uiso 0.2429(19) 1 calc R U P A 2
H11F H 0.6375 0.2775 0.6701 0.053 Uiso 0.2429(19) 1 calc R U P A 2
C12' C 0.5250(11) 0.1916(5) 0.8899(8) 0.0313(16) Uani 0.2429(19) 1 d D U P A 2
H12C H 0.6189 0.2309 0.9107 0.038 Uiso 0.2429(19) 1 calc R U P A 2
H12D H 0.5802 0.1428 0.9181 0.038 Uiso 0.2429(19) 1 calc R U P A 2
C13' C 0.3595(8) 0.2061(3) 0.9813(5) 0.0375(12) Uani 0.2429(19) 1 d D U P A 2
H13C H 0.2694 0.1649 0.9674 0.045 Uiso 0.2429(19) 1 calc R U P A 2
H13D H 0.4000 0.2071 1.0845 0.045 Uiso 0.2429(19) 1 calc R U P A 2
O1' O 0.2727(5) 0.2754(2) 0.9439(4) 0.0399(10) Uani 0.2429(19) 1 d D U P A 2
H1' H 0.1756 0.2671 0.8942 0.060 Uiso 0.2429(19) 1 calc R U P A 2
N3C N 0.445(2) 0.1668(6) 0.7988(9) 0.0346(12) Uani 0.227(3) 1 d D U P B 3
C11C C 0.433(2) 0.1533(8) 0.9532(14) 0.040(3) Uani 0.227(3) 1 d D U P B 3
H11G H 0.3810 0.1034 0.9689 0.060 Uiso 0.227(3) 1 calc R U P B 3
H11H H 0.5565 0.1563 0.9993 0.060 Uiso 0.227(3) 1 calc R U P B 3
H11I H 0.3531 0.1912 0.9951 0.060 Uiso 0.227(3) 1 calc R U P B 3
C12C C 0.5188(19) 0.2383(7) 0.7529(12) 0.0324(18) Uani 0.227(3) 1 d D U P B 3
H12E H 0.5974 0.2300 0.6694 0.039 Uiso 0.227(3) 1 calc R U P B 3
H12F H 0.5978 0.2594 0.8324 0.039 Uiso 0.227(3) 1 calc R U P B 3
C13C C 0.369(2) 0.2947(8) 0.7111(14) 0.034(2) Uani 0.227(3) 1 d D U P B 3
H13E H 0.4267 0.3423 0.6813 0.041 Uiso 0.227(3) 1 calc R U P B 3
H13F H 0.2932 0.2753 0.6284 0.041 Uiso 0.227(3) 1 calc R U P B 3
O1C O 0.257(3) 0.3076(9) 0.8300(16) 0.0379(9) Uani 0.227(3) 1 d D U P B 3
H1C H 0.1728 0.2751 0.8308 0.057 Uiso 0.227(3) 1 calc R U P B 3


_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 1.138(7) . ?
C1 C3 1.418(6) . ?
N2 C2 1.156(7) . ?
C2 C3 1.430(6) . ?
C3 C4 1.373(6) . ?
C4 C5 1.430(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(7) . ?
C5 C10 1.418(7) . ?
C6 C7 1.371(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(4) . ?
C7 H7 0.9500 . ?
C8 N3 1.402(6) . ?
C8 C9 1.423(6) . ?
C9 C10 1.372(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N3 C11 1.455(6) . ?
N3 C12 1.458(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.529(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O1 1.430(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O1 H1 0.8400 . ?
N1' C1' 1.161(11) . ?
C1' C3' 1.429(10) . ?
N2' C2' 1.136(10) . ?
C2' C3' 1.440(10) . ?
C3' C4' 1.346(10) . ?
C4' C5' 1.424(10) . ?
C4' H4' 0.9500 . ?
C5' C10' 1.398(11) . ?
C5' C6' 1.399(11) . ?
C6' C7' 1.381(10) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.399(7) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.382(9) . ?
C8' N3' 1.478(11) . ?
C9' C10' 1.371(10) . ?
C9' H9' 0.9500 . ?
C10' H10' 0.9500 . ?
N3' C12' 1.455(9) . ?
N3' C11' 1.474(10) . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' C13' 1.517(6) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
C13' O1' 1.425(6) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
O1' H1' 0.8400 . ?
N3C C12C 1.454(11) . ?
N3C C11C 1.457(12) . ?
C11C H11G 0.9800 . ?
C11C H11H 0.9800 . ?
C11C H11I 0.9800 . ?
C12C C13C 1.518(12) . ?
C12C H12E 0.9900 . ?
C12C H12F 0.9900 . ?
C13C O1C 1.415(13) . ?
C13C H13E 0.9900 . ?
C13C H13F 0.9900 . ?
O1C H1C 0.8400 . ?

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
N1 C1 C3 179.2(10) . . ?
N2 C2 C3 178.8(7) . . ?
C4 C3 C1 123.7(6) . . ?
C4 C3 C2 119.7(6) . . ?
C1 C3 C2 116.6(5) . . ?
C3 C4 C5 130.4(7) . . ?
C3 C4 H4 114.8 . . ?
C5 C4 H4 114.8 . . ?
C6 C5 C10 116.4(6) . . ?
C6 C5 C4 124.9(7) . . ?
C10 C5 C4 118.7(7) . . ?
C7 C6 C5 122.2(5) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
N3 C8 C7 128.8(5) . . ?
N3 C8 C9 112.8(5) . . ?
C7 C8 C9 118.4(4) . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 122.7(6) . . ?
C9 C10 H10 118.7 . . ?
C5 C10 H10 118.7 . . ?
C8 N3 C11 125.7(4) . . ?
C8 N3 C12 115.7(4) . . ?
C11 N3 C12 118.6(4) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 111.6(5) . . ?
N3 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O1 C13 C12 111.2(4) . . ?
O1 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O1 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 O1 H1 109.5 . . ?
N1' C1' C3' 178.6(14) . . ?
N2' C2' C3' 178.1(15) . . ?
C4' C3' C1' 126.8(11) . . ?
C4' C3' C2' 118.7(9) . . ?
C1' C3' C2' 114.4(9) . . ?
C3' C4' C5' 132.2(12) . . ?
C3' C4' H4' 113.9 . . ?
C5' C4' H4' 113.9 . . ?
C10' C5' C6' 116.9(9) . . ?
C10' C5' C4' 114.6(10) . . ?
C6' C5' C4' 128.5(10) . . ?
C7' C6' C5' 120.0(9) . . ?
C7' C6' H6' 120.0 . . ?
C5' C6' H6' 120.0 . . ?
C6' C7' C8' 123.1(8) . . ?
C6' C7' H7' 118.4 . . ?
C8' C7' H7' 118.4 . . ?
C9' C8' C7' 115.8(7) . . ?
C9' C8' N3' 146.4(8) . . ?
C7' C8' N3' 97.4(7) . . ?
C10' C9' C8' 122.0(9) . . ?
C10' C9' H9' 119.0 . . ?
C8' C9' H9' 119.0 . . ?
C9' C10' C5' 122.0(10) . . ?
C9' C10' H10' 119.0 . . ?
C5' C10' H10' 119.0 . . ?
C12' N3' C11' 115.9(7) . . ?
C12' N3' C8' 106.9(7) . . ?
C11' N3' C8' 136.1(8) . . ?
N3' C11' H11D 109.5 . . ?
N3' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
N3' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N3' C12' C13' 113.8(6) . . ?
N3' C12' H12C 108.8 . . ?
C13' C12' H12C 108.8 . . ?
N3' C12' H12D 108.8 . . ?
C13' C12' H12D 108.8 . . ?
H12C C12' H12D 107.7 . . ?
O1' C13' C12' 111.3(5) . . ?
O1' C13' H13C 109.4 . . ?
C12' C13' H13C 109.4 . . ?
O1' C13' H13D 109.4 . . ?
C12' C13' H13D 109.4 . . ?
H13C C13' H13D 108.0 . . ?
C13' O1' H1' 109.5 . . ?
C12C N3C C11C 117.9(8) . . ?
N3C C11C H11G 109.5 . . ?
N3C C11C H11H 109.5 . . ?
H11G C11C H11H 109.5 . . ?
N3C C11C H11I 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
N3C C12C C13C 112.9(10) . . ?
N3C C12C H12E 109.0 . . ?
C13C C12C H12E 109.0 . . ?
N3C C12C H12F 109.0 . . ?
C13C C12C H12F 109.0 . . ?
H12E C12C H12F 107.8 . . ?
O1C C13C C12C 109.6(10) . . ?
O1C C13C H13E 109.7 . . ?
C12C C13C H13E 109.7 . . ?
O1C C13C H13F 109.7 . . ?
C12C C13C H13F 109.7 . . ?
H13E C13C H13F 108.2 . . ?
C13C O1C H1C 109.5 . . ?

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
C2 C3 C4 C5 179.7(16) . . . . ?
C3 C4 C5 C6 2(3) . . . . ?
C3 C4 C5 C10 -177.6(16) . . . . ?
C10 C5 C6 C7 -1(2) . . . . ?
C4 C5 C6 C7 179.8(15) . . . . ?
C5 C6 C7 C8 0.2(17) . . . . ?
C6 C7 C8 N3 -178.1(9) . . . . ?
C6 C7 C8 C9 0.5(11) . . . . ?
N3 C8 C9 C10 178.4(7) . . . . ?
C7 C8 C9 C10 -0.4(10) . . . . ?
C8 C9 C10 C5 -0.5(14) . . . . ?
C6 C5 C10 C9 1(2) . . . . ?
C4 C5 C10 C9 -179.6(13) . . . . ?
C7 C8 N3 C11 173.0(7) . . . . ?
C9 C8 N3 C11 -5.7(9) . . . . ?
C7 C8 N3 C12 -7.7(10) . . . . ?
C9 C8 N3 C12 173.7(6) . . . . ?
C8 N3 C12 C13 82.9(6) . . . . ?
C11 N3 C12 C13 -97.7(6) . . . . ?
N3 C12 C13 O1 56.8(7) . . . . ?
C1' C3' C4' C5' -1(4) . . . . ?
C2' C3' C4' C5' -177(3) . . . . ?
C3' C4' C5' C10' 175(3) . . . . ?
C3' C4' C5' C6' -6(5) . . . . ?
C10' C5' C6' C7' 2(3) . . . . ?
C4' C5' C6' C7' -178(2) . . . . ?
C5' C6' C7' C8' -1(3) . . . . ?
C6' C7' C8' C9' -1.6(18) . . . . ?
C6' C7' C8' N3' 173.9(14) . . . . ?
C7' C8' C9' C10' 3.4(17) . . . . ?
N3' C8' C9' C10' -168.4(17) . . . . ?
C8' C9' C10' C5' -3(2) . . . . ?
C6' C5' C10' C9' 0(3) . . . . ?
C4' C5' C10' C9' -180(2) . . . . ?
C9' C8' N3' C12' -4(2) . . . . ?
C7' C8' N3' C12' -176.7(8) . . . . ?
C9' C8' N3' C11' -170.9(15) . . . . ?
C7' C8' N3' C11' 16.5(17) . . . . ?
C11' N3' C12' C13' 94.5(10) . . . . ?
C8' N3' C12' C13' -75.4(10) . . . . ?
N3' C12' C13' O1' -57.7(8) . . . . ?
C11C N3C C12C C13C -97.8(14) . . . . ?
N3C C12C C13C O1C 59.1(15) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       Luminescent
