# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_M201NH_1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1587045'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;
_audit_creation_date             2017-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_systematic        M201NH
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.48
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 0.01920 0.00962 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 0.05239 0.03376 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 0.03256 0.01839 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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y,-z+1/2
4 -x+1/2,-y+1/2,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y,z-1/2
8 x-1/2,y-1/2,-z-1/2

_symmetry_Int_Tables_number      60
_cell_length_a                   21.755(4)
_cell_length_b                   11.303(2)
_cell_length_c                   16.615(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4085.8(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    273.5
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      2.66
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6565
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0613 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1797.9144
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24806
_diffrn_reflns_theta_full        72.4294
_diffrn_reflns_theta_max         72.43
_diffrn_reflns_theta_min         5.15
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9916
_diffrn_measured_fraction_theta_max 0.9916
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              26
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3276
_reflns_number_total             4010
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.3653
_refine_diff_density_min         -0.4662
_refine_diff_density_rms         0.0442
_refine_ls_d_res_high            0.8086
_refine_ls_d_res_low             8.5869
_refine_ls_goodness_of_fit_ref   1.0462
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.0462
_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)+(0.0652P)²+1.0980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1234
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2a,H2b)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C5(H5a,H5b), C20(H20a,H20b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18)
2.d Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C26(H26a,H26b,H26c)
;
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
O1 O 0.34618(5) 0.45389(12) 0.43849(8) 0.0544(3) Uani 1.000000 .
O2 O 0.45608(6) 0.78198(10) 0.36769(8) 0.0575(3) Uani 1.000000 .
O3 O 0.64853(6) -0.08926(10) 0.46490(9) 0.0580(4) Uani 1.000000 .
O4 O 0.80578(6) 0.41381(12) 0.19978(10) 0.0645(4) Uani 1.000000 .
N1 N 0.38855(6) 0.63131(13) 0.39709(8) 0.0453(3) Uani 1.000000 .
N2 N 0.33411(7) 0.69750(15) 0.39353(10) 0.0561(4) Uani 1.000000 .
H2a H 0.30468(17) 0.6587(6) 0.4162(9) 0.0673(5) Uiso 1.000000 GR
H2b H 0.3395(2) 0.7633(6) 0.4189(8) 0.0673(5) Uiso 1.000000 GR
C1 C 0.38982(7) 0.51090(15) 0.41575(9) 0.0409(4) Uani 1.000000 .
C2 C 0.45490(7) 0.47454(14) 0.40147(9) 0.0373(3) Uani 1.000000 .
C3 C 0.48156(7) 0.36367(13) 0.40559(9) 0.0366(3) Uani 1.000000 .
C4 C 0.44651(7) 0.25423(14) 0.42945(11) 0.0437(4) Uani 1.000000 .
H4a H 0.44970(7) 0.24271(14) 0.48715(11) 0.0525(5) Uiso 1.000000 R
H4b H 0.40341(7) 0.26415(14) 0.41612(11) 0.0525(5) Uiso 1.000000 R
C5 C 0.47177(7) 0.14623(14) 0.38615(11) 0.0440(4) Uani 1.000000 .
H5a H 0.45044(7) 0.07579(14) 0.40436(11) 0.0528(5) Uiso 1.000000 R
H5b H 0.46524(7) 0.15419(14) 0.32866(11) 0.0528(5) Uiso 1.000000 R
C6 C 0.53932(7) 0.13494(13) 0.40338(10) 0.0378(3) Uani 1.000000 .
C7 C 0.56576(7) 0.02764(13) 0.42387(11) 0.0424(4) Uani 1.000000 .
H7 H 0.54197(7) -0.04071(13) 0.42325(11) 0.0509(5) Uiso 1.000000 R
C8 C 0.62742(7) 0.02083(13) 0.44533(10) 0.0419(4) Uani 1.000000 .
C9 C 0.66307(7) 0.12304(14) 0.44617(11) 0.0421(4) Uani 1.000000 .
H9 H 0.70432(7) 0.11953(14) 0.46069(11) 0.0506(5) Uiso 1.000000 R
C10 C 0.63649(7) 0.23017(13) 0.42516(10) 0.0396(4) Uani 1.000000 .
H10 H 0.66047(7) 0.29828(13) 0.42627(10) 0.0475(4) Uiso 1.000000 R
C11 C 0.57492(7) 0.23905(13) 0.40240(9) 0.0352(3) Uani 1.000000 .
C12 C 0.54455(7) 0.35422(12) 0.38494(9) 0.0345(3) Uani 1.000000 .
C13 C 0.57628(7) 0.45399(12) 0.35368(9) 0.0336(3) Uani 1.000000 .
C14 C 0.63605(7) 0.44514(12) 0.31153(9) 0.0336(3) Uani 1.000000 .
C15 C 0.65130(7) 0.34856(13) 0.26266(10) 0.0388(4) Uani 1.000000 .
H15 H 0.62295(7) 0.28789(13) 0.25550(10) 0.0466(4) Uiso 1.000000 R
C16 C 0.70732(8) 0.34201(14) 0.22522(10) 0.0432(4) Uani 1.000000 .
H16 H 0.71661(8) 0.27762(14) 0.19257(10) 0.0518(5) Uiso 1.000000 R
C17 C 0.75026(8) 0.43170(14) 0.23609(10) 0.0424(4) Uani 1.000000 .
C18 C 0.73470(7) 0.53183(14) 0.27970(9) 0.0399(4) Uani 1.000000 .
H18 H 0.76269(7) 0.59359(14) 0.28462(9) 0.0478(4) Uiso 1.000000 R
C19 C 0.67729(7) 0.54014(13) 0.31613(9) 0.0350(3) Uani 1.000000 .
C20 C 0.65603(8) 0.65050(13) 0.35879(10) 0.0414(4) Uani 1.000000 .
H20a H 0.66008(8) 0.64035(13) 0.41652(10) 0.0496(4) Uiso 1.000000 R
H20b H 0.68127(8) 0.71715(13) 0.34267(10) 0.0496(4) Uiso 1.000000 R
C21 C 0.58909(7) 0.67432(13) 0.33734(10) 0.0412(4) Uani 1.000000 .
H21a H 0.57456(7) 0.74300(13) 0.36674(10) 0.0495(4) Uiso 1.000000 R
H21b H 0.58574(7) 0.69113(13) 0.28026(10) 0.0495(4) Uiso 1.000000 R
C22 C 0.54975(7) 0.56826(13) 0.35807(9) 0.0352(3) Uani 1.000000 .
C23 C 0.48882(7) 0.57506(13) 0.38071(9) 0.0371(3) Uani 1.000000 .
C24 C 0.44648(8) 0.67840(15) 0.38055(10) 0.0421(4) Uani 1.000000 .
C25 C 0.70958(9) -0.09979(17) 0.49394(14) 0.0630(6) Uani 1.000000 .
H25a H 0.73791(9) -0.0789(13) 0.4520(3) 0.0945(8) Uiso 1.000000 GR
H25b H 0.7152(2) -0.0477(10) 0.5390(6) 0.0945(8) Uiso 1.000000 GR
H25c H 0.7170(2) -0.1799(4) 0.5105(9) 0.0945(8) Uiso 1.000000 GR
C26 C 0.85430(9) 0.4929(2) 0.21653(17) 0.0775(7) Uani 1.000000 .
H26a H 0.8460(4) 0.5679(6) 0.1917(9) 0.1162(11) Uiso 1.000000 GR
H26b H 0.8579(6) 0.5032(13) 0.27369(17) 0.1162(11) Uiso 1.000000 GR
H26c H 0.89203(17) 0.4614(8) 0.1956(10) 0.1162(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
O1 C1 1.208(2) . ?
O2 C24 1.208(2) . ?
O3 C8 1.3656(19) . ?
O3 C25 1.418(2) . ?
O4 C17 1.3651(19) . ?
O4 C26 1.411(2) . ?
N1 N2 1.4022(18) . ?
N1 C1 1.396(2) . ?
N1 C24 1.395(2) . ?
N2 H2a 0.8626 . ?
N2 H2b 0.8622 . ?
C1 C2 1.493(2) . ?
C2 C3 1.383(2) . ?
C2 C23 1.398(2) . ?
C3 C4 1.506(2) . ?
C3 C12 1.417(2) . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C4 C5 1.520(2) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C5 C6 1.503(2) . ?
C6 C7 1.385(2) . ?
C6 C11 1.409(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(2) . ?
C8 C9 1.391(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(2) . ?
C11 C12 1.488(2) . ?
C12 C13 1.421(2) . ?
C13 C14 1.480(2) . ?
C13 C22 1.417(2) . ?
C14 C15 1.400(2) . ?
C14 C19 1.401(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(2) . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(2) . ?
C19 C20 1.507(2) . ?
C20 H20a 0.9700 . ?
C20 H20b 0.9700 . ?
C20 C21 1.523(2) . ?
C21 H21a 0.9700 . ?
C21 H21b 0.9700 . ?
C21 C22 1.513(2) . ?
C22 C23 1.380(2) . ?
C23 C24 1.488(2) . ?
C25 H25a 0.9600 . ?
C25 H25b 0.9600 . ?
C25 H25c 0.9600 . ?
C26 H26a 0.9600 . ?
C26 H26b 0.9600 . ?
C26 H26c 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
C25 O3 C8 118.19(14) . . ?
C26 O4 C17 118.75(15) . . ?
C1 N1 N2 123.11(14) . . ?
C24 N1 N2 123.44(14) . . ?
C24 N1 C1 113.44(13) . . ?
H2a N2 N1 109.7 . . ?
H2b N2 N1 108.9 . . ?
H2b N2 H2a 109.0 . . ?
N1 C1 O1 125.02(15) . . ?
C2 C1 O1 130.40(16) . . ?
C2 C1 N1 104.58(13) . . ?
C3 C2 C1 129.74(14) . . ?
C23 C2 C1 108.42(13) . . ?
C23 C2 C3 121.83(14) . . ?
C4 C3 C2 123.03(14) . . ?
C12 C3 C2 117.52(13) . . ?
C12 C3 C4 119.44(13) . . ?
H4a C4 C3 109.52(9) . . ?
H4b C4 C3 109.52(8) . . ?
H4b C4 H4a 108.1 . . ?
C5 C4 C3 110.62(13) . . ?
C5 C4 H4a 109.52(10) . . ?
C5 C4 H4b 109.52(8) . . ?
H5a C5 C4 109.80(8) . . ?
H5b C5 C4 109.80(10) . . ?
H5b C5 H5a 108.2 . . ?
C6 C5 C4 109.36(13) . . ?
C6 C5 H5a 109.80(8) . . ?
C6 C5 H5b 109.80(9) . . ?
C7 C6 C5 121.83(13) . . ?
C11 C6 C5 117.67(13) . . ?
C11 C6 C7 120.41(14) . . ?
H7 C7 C6 119.59(9) . . ?
C8 C7 C6 120.82(14) . . ?
C8 C7 H7 119.59(9) . . ?
C7 C8 O3 115.84(14) . . ?
C9 C8 O3 124.53(15) . . ?
C9 C8 C7 119.63(14) . . ?
H9 C9 C8 120.32(9) . . ?
C10 C9 C8 119.36(14) . . ?
C10 C9 H9 120.32(9) . . ?
H10 C10 C9 118.96(9) . . ?
C11 C10 C9 122.09(14) . . ?
C11 C10 H10 118.96(9) . . ?
C10 C11 C6 117.67(14) . . ?
C12 C11 C6 119.27(13) . . ?
C12 C11 C10 122.80(13) . . ?
C11 C12 C3 116.62(13) . . ?
C13 C12 C3 119.92(13) . . ?
C13 C12 C11 123.36(13) . . ?
C14 C13 C12 123.11(13) . . ?
C22 C13 C12 120.46(13) . . ?
C22 C13 C14 116.35(12) . . ?
C15 C14 C13 122.35(13) . . ?
C19 C14 C13 118.99(13) . . ?
C19 C14 C15 118.52(14) . . ?
H15 C15 C14 119.47(9) . . ?
C16 C15 C14 121.07(14) . . ?
C16 C15 H15 119.47(9) . . ?
H16 C16 C15 120.03(9) . . ?
C17 C16 C15 119.94(15) . . ?
C17 C16 H16 120.03(9) . . ?
C16 C17 O4 115.40(14) . . ?
C18 C17 O4 124.62(15) . . ?
C18 C17 C16 119.95(15) . . ?
H18 C18 C17 119.93(9) . . ?
C19 C18 C17 120.13(14) . . ?
C19 C18 H18 119.93(9) . . ?
C18 C19 C14 119.95(14) . . ?
C20 C19 C14 117.61(13) . . ?
C20 C19 C18 122.41(13) . . ?
H20a C20 C19 109.83(9) . . ?
H20b C20 C19 109.83(8) . . ?
H20b C20 H20a 108.3 . . ?
C21 C20 C19 109.25(13) . . ?
C21 C20 H20a 109.83(9) . . ?
C21 C20 H20b 109.83(8) . . ?
H21a C21 C20 109.59(8) . . ?
H21b C21 C20 109.59(9) . . ?
H21b C21 H21a 108.1 . . ?
C22 C21 C20 110.34(12) . . ?
C22 C21 H21a 109.59(8) . . ?
C22 C21 H21b 109.59(9) . . ?
C21 C22 C13 118.70(13) . . ?
C23 C22 C13 117.14(13) . . ?
C23 C22 C21 124.15(13) . . ?
C22 C23 C2 121.94(14) . . ?
C24 C23 C2 108.17(14) . . ?
C24 C23 C22 129.64(14) . . ?
N1 C24 O2 124.09(15) . . ?
C23 C24 O2 130.86(16) . . ?
C23 C24 N1 105.03(13) . . ?
H25a C25 O3 109.5 . . ?
H25b C25 O3 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 O3 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
H26a C26 O4 109.5 . . ?
H26b C26 O4 109.5 . . ?
H26b C26 H26a 109.5 . . ?
H26c C26 O4 109.5 . . ?
H26c C26 H26a 109.5 . . ?
H26c C26 H26b 109.5 . . ?

_olex2_submission_original_sample_id M201NH
_olex2_submission_special_instructions 'No special instructions were received'
