# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_rnn001a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1516420'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
_audit_creation_date             2016-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_systematic        
'Dimethyl (E)-2,5- bis((diphenylmethylene)amino)hex-2-enedioate'
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.63
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      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

_symmetry_Int_Tables_number      2
_cell_length_a                   8.9150(9)
_cell_length_b                   9.1378(9)
_cell_length_c                   9.7366(9)
_cell_angle_alpha                78.555(5)
_cell_angle_beta                 88.795(6)
_cell_angle_gamma                63.698(5)
_cell_volume                     694.90(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3398
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.274
_cell_measurement_theta_min      2.543
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0514 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.9299.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             280.1355
_exptl_crystal_recrystallization_method 
'Crystallized from dichloromethane via buffer diffusion of hexanes'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14669
_diffrn_reflns_theta_full        29.8866
_diffrn_reflns_theta_max         29.89
_diffrn_reflns_theta_min         2.14
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.9824
_diffrn_measured_fraction_theta_max 0.9824
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2940
_reflns_number_total             3960
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.4022
_refine_diff_density_min         -0.3016
_refine_diff_density_rms         0.0761
_refine_ls_d_res_high            0.7132
_refine_ls_d_res_low             9.5153
_refine_ls_goodness_of_fit_ref   1.0401
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.0401
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.5863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1461
_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
2. Others
 Fixed Sof: C1A(0.5) C1B(0.5) H1B(0.5) H1Aa(0.5) H1A(0.5) H1Ac(0.5) H2a(0.5)
 H2(0.5) H1Ba(0.5) H1Bb(0.5) H2(0.5) H1A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_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
_atom_site_disorder_group
C1A C 0.4690(4) 0.5552(5) 0.9290(4) 0.0226(7) Uani 0.500000 . -1
C1B C 0.4319(4) 0.4716(5) 0.9383(3) 0.0223(7) Uani 0.500000 . 1
C2 C 0.5203(2) 0.5071(3) 0.81200(19) 0.0294(4) Uani 1.000000 . .
C3 C 0.4107(2) 0.5301(3) 0.68624(19) 0.0293(4) Uani 1.000000 . .
O1 O 0.4345(2) 0.42512(18) 0.62024(15) 0.0437(4) Uani 1.000000 . .
O2 O 0.28160(19) 0.6799(2) 0.65919(19) 0.0579(5) Uani 1.000000 . .
C4 C 0.1692(3) 0.7183(3) 0.5383(3) 0.0487(6) Uani 1.000000 . .
H4a H 0.2317(5) 0.708(2) 0.4539(4) 0.0730(9) Uiso 1.000000 GR .
H4b H 0.1198(17) 0.6401(14) 0.5515(8) 0.0730(9) Uiso 1.000000 GR .
H4c H 0.0797(13) 0.8327(8) 0.5275(11) 0.0730(9) Uiso 1.000000 GR .
N1 N 0.68833(19) 0.38232(19) 0.80866(15) 0.0272(3) Uani 1.000000 . .
C5 C 0.8090(2) 0.4226(2) 0.78977(17) 0.0228(3) Uani 1.000000 . .
C6 C 0.7860(2) 0.5993(2) 0.76092(17) 0.0219(3) Uani 1.000000 . .
C7 C 0.8173(2) 0.6650(2) 0.86772(19) 0.0276(4) Uani 1.000000 . .
H7 H 0.8566(2) 0.5967(2) 0.95906(19) 0.0332(5) Uiso 1.000000 R .
C8 C 0.7917(2) 0.8295(2) 0.8423(2) 0.0310(4) Uani 1.000000 . .
H8 H 0.8122(2) 0.8737(2) 0.9162(2) 0.0371(5) Uiso 1.000000 R .
C9 C 0.7363(2) 0.9292(2) 0.7090(2) 0.0306(4) Uani 1.000000 . .
H9 H 0.7187(2) 1.0419(2) 0.6913(2) 0.0368(5) Uiso 1.000000 R .
C10 C 0.7067(3) 0.8642(2) 0.6016(2) 0.0343(4) Uani 1.000000 . .
H10 H 0.6699(3) 0.9321(2) 0.5098(2) 0.0412(5) Uiso 1.000000 R .
C11 C 0.7307(2) 0.6997(2) 0.62727(19) 0.0307(4) Uani 1.000000 . .
H11 H 0.7092(2) 0.6560(2) 0.55333(19) 0.0369(5) Uiso 1.000000 R .
C12 C 0.9812(2) 0.2842(2) 0.79495(17) 0.0232(3) Uani 1.000000 . .
C13 C 1.0038(3) 0.1193(2) 0.8284(2) 0.0330(4) Uani 1.000000 . .
H13 H 0.9099(3) 0.0975(2) 0.8484(2) 0.0396(5) Uiso 1.000000 R .
C14 C 1.1614(3) -0.0120(3) 0.8324(2) 0.0409(5) Uani 1.000000 . .
H14 H 1.1748(3) -0.1234(3) 0.8534(2) 0.0490(6) Uiso 1.000000 R .
C15 C 1.2997(3) 0.0170(2) 0.8064(2) 0.0361(5) Uani 1.000000 . .
H15 H 1.4081(3) -0.0740(2) 0.8108(2) 0.0433(5) Uiso 1.000000 R .
C16 C 1.2794(2) 0.1789(2) 0.7738(2) 0.0327(4) Uani 1.000000 . .
H16 H 1.3742(2) 0.1995(2) 0.7554(2) 0.0393(5) Uiso 1.000000 R .
C17 C 1.1212(2) 0.3120(2) 0.76771(19) 0.0275(4) Uani 1.000000 . .
H17 H 1.1084(2) 0.4231(2) 0.74470(19) 0.0329(4) Uiso 1.000000 R .
H1Ba H 0.436(5) 0.369(5) 0.939(4) 0.019(9) Uiso 0.500000 . 1
H1Bb H 0.313(4) 0.555(4) 0.937(3) 0.002(7) Uiso 0.500000 . 1
H2 H 0.505(5) 0.634(5) 0.809(4) 0.019(9) Uiso 0.500000 . 1
H1A H 0.358(5) 0.617(5) 0.926(4) 0.015(9) Uiso 0.500000 . -1


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
C1A C1B 1.497(5) 2_667 ?
C1A C2 1.303(4) . ?
C1A H1A 0.90(4) . ?
C1B C1B 2.014(7) 2_667 ?
C1B C2 1.505(4) . ?
C1B H1Ba 0.92(4) . ?
C1B H1Bb 0.99(3) . ?
C2 C3 1.505(3) . ?
C2 N1 1.430(2) . ?
C2 H2 1.10(4) . ?
C3 O1 1.198(2) . ?
C3 O2 1.320(3) . ?
O2 C4 1.445(3) . ?
C4 H4a 0.9800 . ?
C4 H4b 0.9800 . ?
C4 H4c 0.9800 . ?
N1 C5 1.282(2) . ?
C5 C6 1.502(2) . ?
C5 C12 1.489(2) . ?
C6 C7 1.389(2) . ?
C6 C11 1.390(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(2) . ?
C12 C17 1.390(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 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
H1A C1A C2 113(2) . . ?
C2 C1B C1A 110.5(3) . 2_667 ?
H1Bb C1B H1Ba 109(3) . . ?
C3 C2 C1A 126.3(2) . . ?
N1 C2 C1A 119.7(2) . . ?
N1 C2 C3 111.59(15) . . ?
H2 C2 C1B 104.4(19) . . ?
O1 C3 C2 124.74(19) . . ?
O2 C3 C2 111.44(16) . . ?
O2 C3 O1 123.81(18) . . ?
C4 O2 C3 116.59(16) . . ?
H4a C4 O2 109.5 . . ?
H4b C4 O2 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 O2 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
C5 N1 C2 120.54(15) . . ?
C6 C5 N1 124.00(16) . . ?
C12 C5 N1 117.08(15) . . ?
C12 C5 C6 118.92(14) . . ?
C7 C6 C5 120.50(15) . . ?
C11 C6 C5 120.28(15) . . ?
C11 C6 C7 119.21(16) . . ?
H7 C7 C6 119.70(10) . . ?
C8 C7 C6 120.60(17) . . ?
C8 C7 H7 119.70(11) . . ?
H8 C8 C7 120.00(11) . . ?
C9 C8 C7 120.00(17) . . ?
C9 C8 H8 120.00(11) . . ?
H9 C9 C8 120.11(11) . . ?
C10 C9 C8 119.79(17) . . ?
C10 C9 H9 120.11(11) . . ?
H10 C10 C9 119.86(11) . . ?
C11 C10 C9 120.28(17) . . ?
C11 C10 H10 119.86(11) . . ?
C10 C11 C6 120.12(17) . . ?
H11 C11 C6 119.94(10) . . ?
H11 C11 C10 119.94(11) . . ?
C13 C12 C5 118.95(16) . . ?
C17 C12 C5 122.62(15) . . ?
C17 C12 C13 118.42(17) . . ?
H13 C13 C12 119.77(11) . . ?
C14 C13 C12 120.47(18) . . ?
C14 C13 H13 119.77(12) . . ?
H14 C14 C13 119.69(12) . . ?
C15 C14 C13 120.62(18) . . ?
C15 C14 H14 119.69(12) . . ?
H15 C15 C14 120.24(12) . . ?
C16 C15 C14 119.53(19) . . ?
C16 C15 H15 120.24(12) . . ?
H16 C16 C15 119.83(12) . . ?
C17 C16 C15 120.34(18) . . ?
C17 C16 H16 119.83(11) . . ?
C16 C17 C12 120.61(17) . . ?
H17 C17 C12 119.69(10) . . ?
H17 C17 C16 119.69(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
