# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_191008irai
_database_code_depnum_ccdc_archive 'CCDC 1976349'
loop_
_audit_author_name
_audit_author_address
'Mohammad Reza Mohammadizadeh'
;Persian Gulf University
Iran
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;
_audit_creation_date             2019-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H23 N1 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4024(2)
_cell_length_b                   11.0210(3)
_cell_length_c                   17.2462(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.347(2)
_cell_angle_gamma                90
_cell_volume                     2167.22(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13381
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.0980
_cell_measurement_theta_min      1.7900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_preparation       
'It has been crysalized from a acetonitrile solusion'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.162
_diffrn_reflns_theta_min         1.786
_diffrn_ambient_temperature      113
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   32.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   32.00    --  -20.00  45.00  90.00  360
  3  ω   -110.00  70.00   0.50   32.00    --  -20.00  45.00  45.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn724Plus with AFC10'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162647000
_diffrn_orient_matrix_UB_12      -0.0444085000
_diffrn_orient_matrix_UB_13      0.0276924000
_diffrn_orient_matrix_UB_21      0.0470844000
_diffrn_orient_matrix_UB_22      0.0184996000
_diffrn_orient_matrix_UB_23      0.0243300000
_diffrn_orient_matrix_UB_31      -0.0372500000
_diffrn_orient_matrix_UB_32      0.0427680000
_diffrn_orient_matrix_UB_33      0.0182344000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4869
_reflns_number_total             6555
_reflns_odcompleteness_completeness 93.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.09
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         6555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.9820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C6(H6), C1(H1), C19(H19), C4(H4), C3(H3), C2(H2), C17(H17),
 C18(H18), C5(H5)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O21 O 0.50872(9) 0.37468(10) 0.34522(6) 0.0245(2) Uani 1 1 d . . . . .
O23 O 0.22857(9) 0.28302(9) 0.18543(6) 0.0247(2) Uani 1 1 d . . . . .
O22 O 0.16937(9) 0.50719(10) 0.06892(6) 0.0263(2) Uani 1 1 d . . . . .
O20 O 0.04616(10) 0.31039(14) 0.46557(6) 0.0435(4) Uani 1 1 d . . . . .
N8 N 0.34998(10) 0.49079(11) 0.31658(6) 0.0179(2) Uani 1 1 d . . . . .
C7 C 0.45838(11) 0.44243(13) 0.30003(8) 0.0171(3) Uani 1 1 d . . . . .
C13A C 0.40860(12) 0.35519(12) 0.13213(8) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.19963(11) 0.56093(14) 0.12763(8) 0.0192(3) Uani 1 1 d . . . . .
C6A C 0.52126(11) 0.48429(13) 0.22777(8) 0.0173(3) Uani 1 1 d . . . . .
C13 C 0.29536(12) 0.36698(13) 0.17401(7) 0.0179(3) Uani 1 1 d . . . . .
C3A C 0.59823(12) 0.44391(13) 0.09812(8) 0.0205(3) Uani 1 1 d . . . . .
C15 C 0.19648(12) 0.40159(14) 0.39554(8) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.165411 0.366184 0.350990 0.026 Uiso 1 1 calc R . . . .
C9 C 0.24060(12) 0.67731(13) 0.27823(8) 0.0211(3) Uani 1 1 d . . . . .
H9A H 0.306765 0.732508 0.276189 0.025 Uiso 1 1 calc R . . . .
H9B H 0.210792 0.678114 0.330789 0.025 Uiso 1 1 calc R . . . .
C10 C 0.14426(12) 0.72302(13) 0.22281(8) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.61085(12) 0.56553(14) 0.23988(8) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.617339 0.604757 0.287462 0.026 Uiso 1 1 calc R . . . .
C1 C 0.40721(13) 0.29300(13) 0.06287(8) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.343170 0.244324 0.050450 0.027 Uiso 1 1 calc R . . . .
C16 C 0.14182(12) 0.38447(15) 0.46700(8) 0.0248(3) Uani 1 1 d . . . . .
C11 C 0.18275(13) 0.69441(14) 0.13975(8) 0.0237(3) Uani 1 1 d . . . . .
H11A H 0.123890 0.724068 0.103605 0.028 Uiso 1 1 calc R . . . .
H11B H 0.255689 0.736328 0.129065 0.028 Uiso 1 1 calc R . . . .
C19 C 0.34437(13) 0.52523(13) 0.45722(8) 0.0226(3) Uani 1 1 d . . . . .
H19 H 0.412797 0.570862 0.454239 0.027 Uiso 1 1 calc R . . . .
C4 C 0.68992(13) 0.52731(15) 0.11326(9) 0.0261(3) Uani 1 1 d . . . . .
H4 H 0.748316 0.539170 0.076619 0.031 Uiso 1 1 calc R . . . .
C3 C 0.59241(13) 0.37761(14) 0.02763(8) 0.0251(3) Uani 1 1 d . . . . .
H3 H 0.652694 0.386006 -0.008051 0.030 Uiso 1 1 calc R . . . .
C2 C 0.50101(14) 0.30189(14) 0.01059(8) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.500809 0.256784 -0.034981 0.031 Uiso 1 1 calc R . . . .
C17 C 0.18686(13) 0.44019(14) 0.53305(8) 0.0244(3) Uani 1 1 d . . . . .
H17 H 0.149746 0.431021 0.580560 0.029 Uiso 1 1 calc R . . . .
C18 C 0.28798(14) 0.50974(14) 0.52722(8) 0.0246(3) Uani 1 1 d . . . . .
H18 H 0.318446 0.546730 0.571428 0.030 Uiso 1 1 calc R . . . .
C5 C 0.69314(13) 0.59039(14) 0.18127(9) 0.0259(3) Uani 1 1 d . . . . .
H5 H 0.749774 0.649963 0.189015 0.031 Uiso 1 1 calc R . . . .
C26 C 0.02754(13) 0.65989(16) 0.23907(10) 0.0293(3) Uani 1 1 d . . . . .
H26A H 0.038977 0.573588 0.239358 0.044 Uiso 1 1 calc GR . . . .
H26B H -0.028305 0.680999 0.199433 0.044 Uiso 1 1 calc GR . . . .
H26C H -0.001335 0.685437 0.288629 0.044 Uiso 1 1 calc GR . . . .
C25 C 0.12903(16) 0.85995(15) 0.23150(10) 0.0340(4) Uani 1 1 d . . . . .
H25A H 0.107370 0.878527 0.283879 0.051 Uiso 1 1 calc GR . . . .
H25B H 0.068671 0.887545 0.196690 0.051 Uiso 1 1 calc GR . . . .
H25C H 0.201470 0.899880 0.219402 0.051 Uiso 1 1 calc GR . . . .
C24 C -0.00421(16) 0.2781(2) 0.53887(10) 0.0496(6) Uani 1 1 d . . . . .
H24A H -0.065845 0.220068 0.530773 0.074 Uiso 1 1 calc GR . . . .
H24B H -0.035668 0.349361 0.563113 0.074 Uiso 1 1 calc GR . . . .
H24C H 0.055203 0.243394 0.571703 0.074 Uiso 1 1 calc GR . . . .
C14 C 0.29680(12) 0.47128(13) 0.39139(7) 0.0179(3) Uani 1 1 d . . . . .
C3A1 C 0.50759(12) 0.42777(12) 0.15375(8) 0.0172(3) Uani 1 1 d . . . . .
C12A C 0.26022(11) 0.49595(13) 0.19163(8) 0.0173(3) Uani 1 1 d . . . . .
C8A C 0.28197(11) 0.55182(13) 0.25927(7) 0.0173(3) Uani 1 1 d . . . . .


_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
O21 C7 1.2202(16) . ?
O23 C13 1.2153(16) . ?
O22 C12 1.2210(17) . ?
O20 C16 1.3626(18) . ?
O20 C24 1.4363(18) . ?
N8 C7 1.3775(17) . ?
N8 C14 1.4451(17) . ?
N8 C8A 1.4217(17) . ?
C7 C6A 1.5134(18) . ?
C13A C13 1.4889(18) . ?
C13A C1 1.3773(19) . ?
C13A C3A1 1.4309(19) . ?
C12 C11 1.498(2) . ?
C12 C12A 1.4830(18) . ?
C6A C6 1.3734(19) . ?
C6A C3A1 1.4282(19) . ?
C13 C12A 1.508(2) . ?
C3A C4 1.415(2) . ?
C3A C3 1.420(2) . ?
C3A C3A1 1.4255(18) . ?
C15 C16 1.3971(19) . ?
C15 C14 1.3800(19) . ?
C9 C10 1.5367(19) . ?
C9 C8A 1.498(2) . ?
C10 C11 1.5335(19) . ?
C10 C26 1.529(2) . ?
C10 C25 1.527(2) . ?
C6 C5 1.410(2) . ?
C1 C2 1.406(2) . ?
C16 C17 1.390(2) . ?
C19 C18 1.382(2) . ?
C19 C14 1.3889(19) . ?
C4 C5 1.364(2) . ?
C3 C2 1.366(2) . ?
C17 C18 1.389(2) . ?
C12A C8A 1.3409(19) . ?

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
C16 O20 C24 117.18(13) . . ?
C7 N8 C14 120.62(11) . . ?
C7 N8 C8A 121.69(11) . . ?
C8A N8 C14 117.45(11) . . ?
O21 C7 N8 121.57(12) . . ?
O21 C7 C6A 119.28(12) . . ?
N8 C7 C6A 118.87(11) . . ?
C1 C13A C13 117.30(12) . . ?
C1 C13A C3A1 120.60(13) . . ?
C3A1 C13A C13 120.65(12) . . ?
O22 C12 C11 123.78(13) . . ?
O22 C12 C12A 120.73(13) . . ?
C12A C12 C11 115.46(12) . . ?
C6 C6A C7 115.41(12) . . ?
C6 C6A C3A1 119.83(12) . . ?
C3A1 C6A C7 123.60(12) . . ?
O23 C13 C13A 123.94(13) . . ?
O23 C13 C12A 121.16(12) . . ?
C13A C13 C12A 114.35(11) . . ?
C4 C3A C3 121.53(13) . . ?
C4 C3A C3A1 119.65(13) . . ?
C3 C3A C3A1 118.80(13) . . ?
C14 C15 C16 119.69(13) . . ?
C8A C9 C10 113.07(11) . . ?
C11 C10 C9 107.82(11) . . ?
C26 C10 C9 110.88(12) . . ?
C26 C10 C11 109.40(12) . . ?
C25 C10 C9 110.14(12) . . ?
C25 C10 C11 109.17(12) . . ?
C25 C10 C26 109.40(13) . . ?
C6A C6 C5 121.00(14) . . ?
C13A C1 C2 121.10(14) . . ?
O20 C16 C15 115.23(13) . . ?
O20 C16 C17 124.85(13) . . ?
C17 C16 C15 119.91(14) . . ?
C12 C11 C10 111.71(12) . . ?
C18 C19 C14 118.67(14) . . ?
C5 C4 C3A 120.39(13) . . ?
C2 C3 C3A 122.03(13) . . ?
C3 C2 C1 119.14(14) . . ?
C18 C17 C16 119.17(13) . . ?
C19 C18 C17 121.49(13) . . ?
C4 C5 C6 120.19(14) . . ?
C15 C14 N8 118.79(12) . . ?
C15 C14 C19 121.03(13) . . ?
C19 C14 N8 120.14(12) . . ?
C6A C3A1 C13A 123.94(12) . . ?
C3A C3A1 C13A 117.93(12) . . ?
C3A C3A1 C6A 118.13(12) . . ?
C12 C12A C13 115.36(11) . . ?
C8A C12A C12 120.58(13) . . ?
C8A C12A C13 124.06(12) . . ?
N8 C8A C9 117.15(11) . . ?
C12A C8A N8 118.99(13) . . ?
C12A C8A C9 123.85(12) . . ?

_olex2_date_sample_data_collection 2019-10-08
_olex2_date_sample_submission    2019-10-08
_olex2_exptl_crystal_mounting_method 'Mitegen Micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.843
