# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_f34p_0m
_database_code_depnum_ccdc_archive 'CCDC 2182574'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'chalcone analogue'
_chemical_name_systematic        
(2E)-3-(4-bromophenyl)-1-[4-(2-oxo-2-phenylethoxy)phenyl]prop-2-en-1-one
_chemical_formula_moiety         'C23 H17 Br O3'
_chemical_formula_sum            'C23 H17 Br O3'
_chemical_formula_weight         421.27
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6262(3)
_cell_length_b                   7.4872(4)
_cell_length_c                   19.2803(10)
_cell_angle_alpha                87.424(2)
_cell_angle_beta                 87.609(2)
_cell_angle_gamma                71.455(2)
_cell_volume                     905.56(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6548
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.531
_exptl_absorpt_coefficient_mu    2.291
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10681
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.211
_diffrn_reflns_theta_min         2.116
_diffrn_ambient_temperature      120.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3704
_reflns_number_total             4424
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.3991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C17(H17), C14(H14), C10(H10), C11(H11), C1(H1), C23(H23),
 C5(H5), C20(H20), C19(H19), C4(H4), C22(H22), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br1 Br 1.20760(3) 0.23778(4) 0.00859(2) 0.03193(8) Uani 1 1 d . . . . .
O2 O 0.2452(2) 0.91323(19) 0.58653(7) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.2184(2) 1.1461(2) 0.68624(8) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.1921(2) 0.3989(2) 0.34030(8) 0.0286(3) Uani 1 1 d . . . . .
C6 C -0.0866(3) 1.1078(3) 0.74518(10) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.2525(3) 0.8109(3) 0.52927(9) 0.0161(4) Uani 1 1 d . . . . .
C12 C 0.3023(3) 0.6013(3) 0.40938(10) 0.0164(4) Uani 1 1 d . . . . .
C18 C 0.6913(3) 0.3300(3) 0.18788(10) 0.0197(4) Uani 1 1 d . . . . .
C16 C 0.5028(3) 0.4623(3) 0.29820(10) 0.0193(4) Uani 1 1 d . . . . .
H16 H 0.602916 0.525890 0.305669 0.023 Uiso 1 1 calc R . . . .
C13 C 0.4593(3) 0.6789(3) 0.42739(10) 0.0177(4) Uani 1 1 d . . . . .
H13 H 0.583474 0.660661 0.398517 0.021 Uiso 1 1 calc R . . . .
C7 C 0.0793(3) 1.0727(3) 0.68794(10) 0.0187(4) Uani 1 1 d . . . . .
C21 C 0.9966(3) 0.2759(3) 0.08100(10) 0.0224(4) Uani 1 1 d . . . . .
C17 C 0.5259(3) 0.3577(3) 0.24272(10) 0.0204(4) Uani 1 1 d . . . . .
H17 H 0.424120 0.294132 0.238183 0.024 Uiso 1 1 calc R . . . .
C15 C 0.3226(3) 0.4809(3) 0.34860(10) 0.0193(4) Uani 1 1 d . . . . .
C14 C 0.4348(3) 0.7814(3) 0.48662(10) 0.0192(4) Uani 1 1 d . . . . .
H14 H 0.542724 0.832274 0.498452 0.023 Uiso 1 1 calc R . . . .
C10 C 0.0930(3) 0.7373(3) 0.51167(10) 0.0181(4) Uani 1 1 d . . . . .
H10 H -0.032033 0.757312 0.540228 0.022 Uiso 1 1 calc R . . . .
C11 C 0.1197(3) 0.6350(3) 0.45207(10) 0.0177(4) Uani 1 1 d . . . . .
H11 H 0.010391 0.586364 0.439858 0.021 Uiso 1 1 calc R . . . .
C1 C -0.0553(3) 1.1965(3) 0.80393(10) 0.0225(4) Uani 1 1 d . . . . .
H1 H 0.069583 1.232000 0.806698 0.027 Uiso 1 1 calc R . . . .
C23 C 0.8741(3) 0.3830(3) 0.19467(11) 0.0222(4) Uani 1 1 d . . . . .
H23 H 0.893441 0.438520 0.236195 0.027 Uiso 1 1 calc R . . . .
C5 C -0.2717(3) 1.0581(3) 0.74121(10) 0.0208(4) Uani 1 1 d . . . . .
H5 H -0.294442 0.996866 0.701555 0.025 Uiso 1 1 calc R . . . .
C20 C 0.8188(3) 0.2214(3) 0.07237(11) 0.0248(4) Uani 1 1 d . . . . .
H20 H 0.800614 0.166211 0.030624 0.030 Uiso 1 1 calc R . . . .
C8 C 0.0652(3) 0.9407(3) 0.63232(10) 0.0175(4) Uani 1 1 d . . . . .
H8A H 0.063665 0.818526 0.653833 0.021 Uiso 1 1 calc R . . . .
H8B H -0.067517 0.996049 0.606434 0.021 Uiso 1 1 calc R . . . .
C19 C 0.6677(3) 0.2492(3) 0.12611(11) 0.0244(4) Uani 1 1 d . . . . .
H19 H 0.544739 0.212376 0.120777 0.029 Uiso 1 1 calc R . . . .
C4 C -0.4222(3) 1.0983(3) 0.79523(11) 0.0248(4) Uani 1 1 d . . . . .
H4 H -0.549046 1.066115 0.792023 0.030 Uiso 1 1 calc R . . . .
C22 C 1.0265(3) 0.3554(3) 0.14148(11) 0.0244(4) Uani 1 1 d . . . . .
H22 H 1.150592 0.390701 0.146488 0.029 Uiso 1 1 calc R . . . .
C2 C -0.2044(3) 1.2335(3) 0.85832(11) 0.0268(4) Uani 1 1 d . . . . .
H2 H -0.180688 1.291872 0.898575 0.032 Uiso 1 1 calc R . . . .
C3 C -0.3898(3) 1.1846(3) 0.85374(11) 0.0273(5) Uani 1 1 d . . . . .
H3 H -0.493284 1.210611 0.890690 0.033 Uiso 1 1 calc R . . . .


_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
Br1 C21 1.8985(19) . ?
O2 C9 1.362(2) . ?
O2 C8 1.420(2) . ?
O1 C7 1.213(2) . ?
O3 C15 1.228(2) . ?
C6 C7 1.496(2) . ?
C6 C1 1.394(3) . ?
C6 C5 1.396(3) . ?
C9 C14 1.396(2) . ?
C9 C10 1.397(3) . ?
C12 C13 1.405(2) . ?
C12 C15 1.486(3) . ?
C12 C11 1.396(2) . ?
C18 C17 1.463(3) . ?
C18 C23 1.402(3) . ?
C18 C19 1.396(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.329(3) . ?
C16 C15 1.483(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C7 C8 1.516(3) . ?
C21 C20 1.382(3) . ?
C21 C22 1.382(3) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.385(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C19 H19 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.382(3) . ?
C22 H22 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 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
C9 O2 C8 117.04(14) . . ?
C1 C6 C7 118.19(16) . . ?
C1 C6 C5 119.31(17) . . ?
C5 C6 C7 122.50(17) . . ?
O2 C9 C14 115.51(15) . . ?
O2 C9 C10 124.63(16) . . ?
C14 C9 C10 119.86(17) . . ?
C13 C12 C15 123.70(16) . . ?
C11 C12 C13 118.07(17) . . ?
C11 C12 C15 118.20(16) . . ?
C23 C18 C17 122.33(18) . . ?
C19 C18 C17 119.49(17) . . ?
C19 C18 C23 118.18(17) . . ?
C17 C16 H16 119.6 . . ?
C17 C16 C15 120.79(17) . . ?
C15 C16 H16 119.6 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.61(16) . . ?
C14 C13 H13 119.7 . . ?
O1 C7 C6 121.58(18) . . ?
O1 C7 C8 121.72(17) . . ?
C6 C7 C8 116.69(15) . . ?
C20 C21 Br1 119.36(15) . . ?
C22 C21 Br1 118.94(14) . . ?
C22 C21 C20 121.69(18) . . ?
C18 C17 H17 116.5 . . ?
C16 C17 C18 127.01(17) . . ?
C16 C17 H17 116.5 . . ?
O3 C15 C12 120.52(17) . . ?
O3 C15 C16 120.77(18) . . ?
C16 C15 C12 118.72(16) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.40(16) . . ?
C13 C14 H14 119.8 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.09(16) . . ?
C11 C10 H10 120.5 . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 121.95(17) . . ?
C10 C11 H11 119.0 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.62(18) . . ?
C2 C1 H1 119.7 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.65(18) . . ?
C22 C23 H23 119.7 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.87(19) . . ?
C4 C5 H5 120.1 . . ?
C21 C20 H20 120.8 . . ?
C21 C20 C19 118.36(19) . . ?
C19 C20 H20 120.8 . . ?
O2 C8 C7 108.09(14) . . ?
O2 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.73(18) . . ?
C20 C19 H19 119.1 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.72(18) . . ?
C3 C4 H4 119.6 . . ?
C21 C22 C23 119.38(18) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.75(18) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_f36p
_database_code_depnum_ccdc_archive 'CCDC 2182577'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'chalcone analogue'
_chemical_name_systematic        
(2E)-3-(3-nitrophenyl)-1-[4-(2-oxo-2-phenylethoxy)phenyl]prop-2-en-1-one
_chemical_formula_moiety         'C23 H17 N O5'
_chemical_formula_sum            'C23 H17 N O5'
_chemical_formula_weight         387.38
_chemical_melting_point          ?
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.3047(12)
_cell_length_b                   11.062(2)
_cell_length_c                   22.299(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.363(3)
_cell_angle_gamma                90
_cell_volume                     1782.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6548
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.618
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         1.846
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3560
_reflns_number_total             4432
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.4139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C5(H5), C19(H19), C14(H14), C16(H16), C17(H17), C1(H1),
 C13(H13), C23(H23), C4(H4), C3(H3), C22(H22), C21(H21), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O -0.11893(11) 0.85676(7) 0.57598(4) 0.01935(19) Uani 1 1 d . . . . .
O3 O 0.36946(11) 0.51882(7) 0.43555(4) 0.02101(19) Uani 1 1 d . . . . .
O1 O -0.40123(12) 0.97715(8) 0.60583(4) 0.0263(2) Uani 1 1 d . . . . .
O4 O 1.16053(13) 0.47868(8) 0.28577(4) 0.0292(2) Uani 1 1 d . . . . .
O5 O 1.33795(13) 0.62920(10) 0.27176(5) 0.0383(3) Uani 1 1 d . . . . .
N1 N 1.20571(14) 0.58532(10) 0.29198(4) 0.0221(2) Uani 1 1 d . . . . .
C12 C 0.27767(15) 0.68719(10) 0.48911(5) 0.0146(2) Uani 1 1 d . . . . .
C6 C -0.53343(15) 0.81778(10) 0.65597(5) 0.0149(2) Uani 1 1 d . . . . .
C9 C 0.01278(15) 0.79459(10) 0.55054(5) 0.0156(2) Uani 1 1 d . . . . .
C15 C 0.40013(15) 0.62394(10) 0.45154(5) 0.0156(2) Uani 1 1 d . . . . .
C18 C 0.83339(15) 0.68979(10) 0.37778(5) 0.0154(2) Uani 1 1 d . . . . .
C20 C 1.09394(15) 0.66552(10) 0.32479(5) 0.0169(2) Uani 1 1 d . . . . .
C11 C 0.15435(15) 0.61736(10) 0.51664(5) 0.0171(2) Uani 1 1 d . . . . .
H11 H 0.160754 0.531779 0.514089 0.021 Uiso 1 1 calc R . . . .
C10 C 0.02291(15) 0.66902(10) 0.54757(5) 0.0175(2) Uani 1 1 d . . . . .
H10 H -0.058829 0.619781 0.566402 0.021 Uiso 1 1 calc R . . . .
C5 C -0.53360(16) 0.69526(10) 0.67046(5) 0.0187(2) Uani 1 1 d . . . . .
H5 H -0.443308 0.642815 0.657980 0.022 Uiso 1 1 calc R . . . .
C7 C -0.39512(15) 0.87162(10) 0.62086(5) 0.0166(2) Uani 1 1 d . . . . .
C19 C 0.94563(15) 0.61542(10) 0.34796(5) 0.0164(2) Uani 1 1 d . . . . .
H19 H 0.920360 0.531379 0.343653 0.020 Uiso 1 1 calc R . . . .
C14 C 0.13954(15) 0.86601(10) 0.52550(5) 0.0170(2) Uani 1 1 d . . . . .
H14 H 0.135769 0.951471 0.529351 0.020 Uiso 1 1 calc R . . . .
C8 C -0.24745(15) 0.78725(10) 0.60367(5) 0.0171(2) Uani 1 1 d . . . . .
H8A H -0.183289 0.746263 0.640274 0.020 Uiso 1 1 calc R . . . .
H8B H -0.304721 0.724778 0.575136 0.020 Uiso 1 1 calc R . . . .
C16 C 0.55807(15) 0.69116(10) 0.43288(5) 0.0183(2) Uani 1 1 d . . . . .
H16 H 0.577765 0.773359 0.444368 0.022 Uiso 1 1 calc R . . . .
C17 C 0.67270(15) 0.63668(10) 0.40000(5) 0.0166(2) Uani 1 1 d . . . . .
H17 H 0.647099 0.554358 0.389925 0.020 Uiso 1 1 calc R . . . .
C1 C -0.66774(16) 0.89359(11) 0.67427(5) 0.0186(2) Uani 1 1 d . . . . .
H1 H -0.667122 0.977428 0.665077 0.022 Uiso 1 1 calc R . . . .
C13 C 0.27058(15) 0.81300(10) 0.49512(5) 0.0163(2) Uani 1 1 d . . . . .
H13 H 0.356500 0.862272 0.478185 0.020 Uiso 1 1 calc R . . . .
C23 C 0.87842(16) 0.81266(10) 0.38386(5) 0.0186(2) Uani 1 1 d . . . . .
H23 H 0.803789 0.864535 0.404127 0.022 Uiso 1 1 calc R . . . .
C4 C -0.66642(17) 0.65005(11) 0.70326(5) 0.0221(3) Uani 1 1 d . . . . .
H4 H -0.664794 0.566878 0.713944 0.026 Uiso 1 1 calc R . . . .
C3 C -0.80063(17) 0.72504(12) 0.72044(5) 0.0223(3) Uani 1 1 d . . . . .
H3 H -0.892141 0.693208 0.742272 0.027 Uiso 1 1 calc R . . . .
C22 C 1.02926(17) 0.86010(11) 0.36097(5) 0.0216(3) Uani 1 1 d . . . . .
H22 H 1.057792 0.943575 0.366154 0.026 Uiso 1 1 calc R . . . .
C21 C 1.13940(16) 0.78654(11) 0.33044(5) 0.0204(2) Uani 1 1 d . . . . .
H21 H 1.242278 0.818398 0.314045 0.025 Uiso 1 1 calc R . . . .
C2 C -0.80174(16) 0.84717(11) 0.70575(5) 0.0215(2) Uani 1 1 d . . . . .
H2 H -0.894511 0.898773 0.717321 0.026 Uiso 1 1 calc R . . . .


_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
O2 C9 1.3708(12) . ?
O2 C8 1.4221(12) . ?
O3 C15 1.2273(14) . ?
O1 C7 1.2134(14) . ?
O4 N1 1.2273(14) . ?
O5 N1 1.2243(13) . ?
N1 C20 1.4706(14) . ?
C12 C15 1.4864(14) . ?
C12 C11 1.3949(14) . ?
C12 C13 1.3999(15) . ?
C6 C5 1.3934(16) . ?
C6 C7 1.4895(14) . ?
C6 C1 1.3960(15) . ?
C9 C10 1.3931(15) . ?
C9 C14 1.3941(15) . ?
C15 C16 1.4821(15) . ?
C18 C19 1.3962(14) . ?
C18 C17 1.4620(15) . ?
C18 C23 1.4004(16) . ?
C20 C19 1.3823(15) . ?
C20 C21 1.3806(17) . ?
C11 H11 0.9500 . ?
C11 C10 1.3845(14) . ?
C10 H10 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.3902(15) . ?
C7 C8 1.5171(15) . ?
C19 H19 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.3812(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.3343(15) . ?
C17 H17 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.3836(16) . ?
C13 H13 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.3833(16) . ?
C4 H4 0.9500 . ?
C4 C3 1.3802(17) . ?
C3 H3 0.9500 . ?
C3 C2 1.3899(18) . ?
C22 H22 0.9500 . ?
C22 C21 1.3900(16) . ?
C21 H21 0.9500 . ?
C2 H2 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
C9 O2 C8 117.12(9) . . ?
O4 N1 C20 118.45(9) . . ?
O5 N1 O4 123.58(10) . . ?
O5 N1 C20 117.96(10) . . ?
C11 C12 C15 117.87(10) . . ?
C11 C12 C13 118.24(10) . . ?
C13 C12 C15 123.75(10) . . ?
C5 C6 C7 122.30(10) . . ?
C5 C6 C1 119.48(10) . . ?
C1 C6 C7 118.22(10) . . ?
O2 C9 C10 124.42(10) . . ?
O2 C9 C14 115.37(10) . . ?
C10 C9 C14 120.20(10) . . ?
O3 C15 C12 120.68(10) . . ?
O3 C15 C16 120.69(10) . . ?
C16 C15 C12 118.62(9) . . ?
C19 C18 C17 118.73(10) . . ?
C19 C18 C23 118.16(10) . . ?
C23 C18 C17 123.10(10) . . ?
C19 C20 N1 117.78(10) . . ?
C21 C20 N1 119.13(10) . . ?
C21 C20 C19 123.08(10) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 121.99(10) . . ?
C10 C11 H11 119.0 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.73(10) . . ?
C11 C10 H10 120.6 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.75(11) . . ?
C4 C5 H5 120.1 . . ?
O1 C7 C6 121.95(10) . . ?
O1 C7 C8 121.40(10) . . ?
C6 C7 C8 116.64(9) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.22(10) . . ?
C20 C19 H19 120.4 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.26(10) . . ?
C13 C14 H14 119.9 . . ?
O2 C8 C7 108.39(9) . . ?
O2 C8 H8A 110.0 . . ?
O2 C8 H8B 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.27(10) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 H17 116.4 . . ?
C16 C17 C18 127.13(11) . . ?
C16 C17 H17 116.4 . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.30(11) . . ?
C2 C1 H1 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.46(10) . . ?
C14 C13 H13 119.8 . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.40(10) . . ?
C22 C23 H23 119.3 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.53(11) . . ?
C3 C4 H4 119.7 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.92(11) . . ?
C2 C3 H3 120.0 . . ?
C23 C22 H22 119.8 . . ?
C23 C22 C21 120.49(11) . . ?
C21 C22 H22 119.8 . . ?
C20 C21 C22 117.62(10) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 H21 121.2 . . ?
C1 C2 C3 120.00(11) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
