# 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_MB_RT_CU
_database_code_depnum_ccdc_archive 'CCDC 1921596'
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.42
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

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

_cell_length_a                   13.9525(7)
_cell_length_b                   6.0895(3)
_cell_length_c                   21.6915(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.412(5)
_cell_angle_gamma                90
_cell_volume                     1776.72(16)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.635
_exptl_crystal_density_diffrn    1.3099
_exptl_crystal_F_000             738.1888
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5771
_diffrn_reflns_theta_full        66.883245
_diffrn_reflns_theta_max         66.88
_diffrn_reflns_theta_min         4.23
_diffrn_measured_fraction_theta_full 0.987029
_diffrn_measured_fraction_theta_max 0.987029
_cell_measurement_temperature    293
_cell_measurement_reflns_used    2366
_cell_measurement_theta_min      4.2230
_cell_measurement_theta_max      66.7590
_exptl_absorpt_correction_T_min  0.92896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -16
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              -11
_reflns_number_gt                2614
_reflns_number_total             3120
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.158518
_refine_diff_density_min         -0.203600
_refine_diff_density_rms         0.044486
_refine_ls_d_res_high            0.838224
_refine_ls_d_res_low             10.455734
_refine_ls_goodness_of_fit_ref   1.010174
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.052335
_refine_ls_R_factor_gt           0.044024
_refine_ls_restrained_S_all      1.010174
_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)+(0.0606P)²+0.6035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.126982
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
C7 C 0.53177(13) 0.4891(3) 0.60937(8) 0.0425(4) Uani 1.000000 .
C2 C 0.58289(13) 0.2108(3) 0.67816(8) 0.0417(4) Uani 1.000000 .
C3 C 0.60203(14) 0.0487(3) 0.72521(9) 0.0472(4) Uani 1.000000 .
C4 C 0.66813(14) -0.1140(3) 0.72062(9) 0.0510(5) Uani 1.000000 .
C5 C 0.71391(15) -0.1182(3) 0.67084(9) 0.0526(5) Uani 1.000000 .
C6 C 0.69545(14) 0.0407(3) 0.62433(9) 0.0515(5) Uani 1.000000 .
C1 C 0.62840(13) 0.2090(3) 0.62760(8) 0.0443(4) Uani 1.000000 .
C8 C 0.47354(13) 0.6727(3) 0.58382(8) 0.0447(4) Uani 1.000000 .
C9 C 0.40693(13) 0.7587(3) 0.61321(8) 0.0424(4) Uani 1.000000 .
C18 C 0.34190(13) 0.9463(3) 0.58579(8) 0.0427(4) Uani 1.000000 .
C23 C 0.24862(15) 0.9725(4) 0.59667(9) 0.0527(5) Uani 1.000000 .
C22 C 0.18609(15) 1.1412(4) 0.56898(10) 0.0562(5) Uani 1.000000 .
C21 C 0.21523(14) 1.2910(3) 0.52938(9) 0.0477(4) Uani 1.000000 .
C20 C 0.30768(14) 1.2696(3) 0.51792(9) 0.0475(4) Uani 1.000000 .
C19 C 0.36931(14) 1.0993(3) 0.54614(8) 0.0458(4) Uani 1.000000 .
C10 C 0.39924(14) 0.6581(3) 0.67161(8) 0.0451(4) Uani 1.000000 .
C11 C 0.45407(13) 0.4811(3) 0.69734(8) 0.0425(4) Uani 1.000000 .
C12 C 0.44924(13) 0.3753(3) 0.75809(8) 0.0442(4) Uani 1.000000 .
C13 C 0.38289(16) 0.2067(4) 0.75800(10) 0.0556(5) Uani 1.000000 .
C14 C 0.38318(18) 0.0999(4) 0.81454(11) 0.0657(6) Uani 1.000000 .
C15 C 0.44924(18) 0.1630(4) 0.87108(10) 0.0655(6) Uani 1.000000 .
C17 C 0.51378(16) 0.4405(4) 0.81547(9) 0.0568(5) Uani 1.000000 .
C16 C 0.51371(18) 0.3330(4) 0.87156(10) 0.0666(6) Uani 1.000000 .
C24 C 0.17356(18) 1.6031(4) 0.46108(11) 0.0662(6) Uani 1.000000 .
H3 H 0.57132(14) 0.0504(3) 0.75837(9) 0.0566(5) Uiso 1.000000 R
H4 H 0.68262(14) -0.2239(3) 0.75148(9) 0.0612(6) Uiso 1.000000 R
H5 H 0.75796(15) -0.2312(3) 0.66911(9) 0.0631(6) Uiso 1.000000 R
H6 H 0.72666(14) 0.0369(3) 0.59142(9) 0.0617(6) Uiso 1.000000 R
H8 H 0.48059(13) 0.7365(3) 0.54632(8) 0.0536(5) Uiso 1.000000 R
H23 H 0.22802(15) 0.8737(4) 0.62325(9) 0.0632(6) Uiso 1.000000 R
H22 H 0.12404(15) 1.1547(4) 0.57692(10) 0.0675(6) Uiso 1.000000 R
H20 H 0.32819(14) 1.3689(3) 0.49145(9) 0.0570(5) Uiso 1.000000 R
H19 H 0.43143(14) 1.0867(3) 0.53828(8) 0.0550(5) Uiso 1.000000 R
H10 H 0.35492(14) 0.7168(3) 0.69252(8) 0.0541(5) Uiso 1.000000 R
H13 H 0.33794(16) 0.1648(4) 0.71994(10) 0.0667(6) Uiso 1.000000 R
H14 H 0.33881(18) -0.0143(4) 0.81431(11) 0.0788(7) Uiso 1.000000 R
H15 H 0.45003(18) 0.0901(4) 0.90890(10) 0.0786(7) Uiso 1.000000 R
H17 H 0.55721(16) 0.5570(4) 0.81622(9) 0.0681(6) Uiso 1.000000 R
H16 H 0.55769(18) 0.3762(4) 0.90985(10) 0.0799(7) Uiso 1.000000 R
H24a H 0.1854(13) 1.5255(5) 0.4253(4) 0.0993(9) Uiso 1.000000 G
H24b H 0.1202(6) 1.7058(18) 0.4462(7) 0.0993(9) Uiso 1.000000 G
H24c H 0.2327(8) 1.681(2) 0.4830(3) 0.0993(9) Uiso 1.000000 G
N1 N 0.59656(12) 0.3815(3) 0.58577(7) 0.0472(4) Uani 1.000000 .
N2 N 0.52020(11) 0.3950(2) 0.66602(6) 0.0409(3) Uani 1.000000 .
O1 O 0.14749(11) 1.4506(3) 0.50379(7) 0.0628(4) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 C8 1.407(3) .
C7 N1 1.324(2) .
C7 N2 1.403(2) .
C2 C3 1.394(3) .
C2 C1 1.406(2) .
C2 N2 1.403(2) .
C3 C4 1.375(3) .
C3 H3 0.9300 .
C4 C5 1.393(3) .
C4 H4 0.9300 .
C5 C6 1.372(3) .
C5 H5 0.9300 .
C6 C1 1.402(3) .
C6 H6 0.9300 .
C1 N1 1.382(2) .
C8 C9 1.363(3) .
C8 H8 0.9300 .
C9 C18 1.482(3) .
C9 C10 1.437(2) .
C18 C23 1.392(3) .
C18 C19 1.389(3) .
C23 C22 1.378(3) .
C23 H23 0.9300 .
C22 C21 1.386(3) .
C22 H22 0.9300 .
C21 C20 1.383(3) .
C21 O1 1.367(2) .
C20 C19 1.382(3) .
C20 H20 0.9300 .
C19 H19 0.9300 .
C10 C11 1.353(3) .
C10 H10 0.9300 .
C11 C12 1.484(2) .
C11 N2 1.386(2) .
C12 C13 1.382(3) .
C12 C17 1.387(3) .
C13 C14 1.387(3) .
C13 H13 0.9300 .
C14 C15 1.379(3) .
C14 H14 0.9300 .
C15 C16 1.369(3) .
C15 H15 0.9300 .
C17 C16 1.382(3) .
C17 H17 0.9300 .
C16 H16 0.9300 .
C24 H24a 0.9600 .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
C24 O1 1.425(3) .

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
N1 C7 C8 128.54(16) . .
N2 C7 C8 118.74(16) . .
N2 C7 N1 112.68(16) . .
C1 C2 C3 121.82(17) . .
N2 C2 C3 133.79(17) . .
N2 C2 C1 104.37(15) . .
C4 C3 C2 117.32(18) . .
H3 C3 C2 121.34(11) . .
H3 C3 C4 121.34(12) . .
C5 C4 C3 121.58(19) . .
H4 C4 C3 119.21(12) . .
H4 C4 C5 119.21(12) . .
C6 C5 C4 121.47(19) . .
H5 C5 C4 119.27(12) . .
H5 C5 C6 119.27(12) . .
C1 C6 C5 118.40(18) . .
H6 C6 C5 120.80(12) . .
H6 C6 C1 120.80(11) . .
C6 C1 C2 119.41(17) . .
N1 C1 C2 111.91(16) . .
N1 C1 C6 128.66(17) . .
C9 C8 C7 121.00(16) . .
H8 C8 C7 119.50(10) . .
H8 C8 C9 119.50(11) . .
C18 C9 C8 121.94(16) . .
C10 C9 C8 117.95(17) . .
C10 C9 C18 120.10(16) . .
C23 C18 C9 121.36(17) . .
C19 C18 C9 121.73(16) . .
C19 C18 C23 116.86(17) . .
C22 C23 C18 121.58(18) . .
H23 C23 C18 119.21(11) . .
H23 C23 C22 119.21(12) . .
C21 C22 C23 120.31(18) . .
H22 C22 C23 119.85(12) . .
H22 C22 C21 119.85(12) . .
C20 C21 C22 119.38(18) . .
O1 C21 C22 115.76(18) . .
O1 C21 C20 124.85(18) . .
C19 C20 C21 119.43(18) . .
H20 C20 C21 120.28(11) . .
H20 C20 C19 120.28(11) . .
C20 C19 C18 122.44(17) . .
H19 C19 C18 118.78(11) . .
H19 C19 C20 118.78(11) . .
C11 C10 C9 122.46(17) . .
H10 C10 C9 118.77(10) . .
H10 C10 C11 118.77(11) . .
C12 C11 C10 123.90(16) . .
N2 C11 C10 118.44(16) . .
N2 C11 C12 117.65(16) . .
C13 C12 C11 120.64(17) . .
C17 C12 C11 120.05(18) . .
C17 C12 C13 119.29(18) . .
C14 C13 C12 120.2(2) . .
H13 C13 C12 119.92(11) . .
H13 C13 C14 119.92(14) . .
C15 C14 C13 120.0(2) . .
H14 C14 C13 120.00(14) . .
H14 C14 C15 120.00(13) . .
C16 C15 C14 120.0(2) . .
H15 C15 C14 120.00(13) . .
H15 C15 C16 120.00(13) . .
C16 C17 C12 120.1(2) . .
H17 C17 C12 119.93(12) . .
H17 C17 C16 119.93(14) . .
C17 C16 C15 120.4(2) . .
H16 C16 C15 119.81(13) . .
H16 C16 C17 119.81(14) . .
H24b C24 H24a 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
O1 C24 H24a 109.5 . .
O1 C24 H24b 109.5 . .
O1 C24 H24c 109.5 . .
C1 N1 C7 104.80(15) . .
C2 N2 C7 106.24(14) . .
C11 N2 C7 121.40(15) . .
C11 N2 C2 132.32(15) . .
C24 O1 C21 117.32(17) . .
_exptl_crystal_description       Block
_exptl_crystal_colour            'yellow red'
_diffrn_ambient_temperature      293
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   'P 1 21/n 1'
##############################################END


