# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_MH4AJK
_database_code_depnum_ccdc_archive 'CCDC 1963584'
loop_
_audit_author_name
_audit_author_address
'Dr nawaz tahir'
;University of sargodha
Pakistan
;
_audit_update_record             
;
2019-11-04 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
4-Methoxy-N'-[(E)-(2-propoxyphenyl)methylidene]benzohydrazide
;
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_iupac          'C18 H20 N2 O3'
_chemical_formula_weight         312.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   23.896(8)
_cell_length_b                   4.9911(17)
_cell_length_c                   13.723(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.782(12)
_cell_angle_gamma                90
_cell_volume                     1596.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2243
_cell_measurement_theta_min      2.622
_cell_measurement_theta_max      28.042
_cell_measurement_temperature    296(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.955
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_reflns_number            18062
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         28.042
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3836
_reflns_number_gt                2243
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_number_reflns         3836
_refine_ls_number_parameters     210
_refine_ls_number_restraints     .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     .
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   .
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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
O1 O 0.45411(6) 0.0524(3) 0.08859(11) 0.0579(4) Uani 1 1 d . . . . .
O2 O 0.13528(5) 0.5081(3) 0.48627(9) 0.0400(4) Uani 1 1 d . . . . .
O3 O 0.31563(6) -0.4059(3) 0.39531(10) 0.0500(4) Uani 1 1 d . . . . .
N1 N 0.28663(7) 0.0261(3) 0.39196(12) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.287893 0.183390 0.366963 0.047 Uiso 1 1 calc R U . . .
N2 N 0.25376(7) -0.0195(3) 0.46112(11) 0.0385(4) Uani 1 1 d . . . . .
C1 C 0.35204(8) -0.1039(4) 0.29044(13) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.33611(9) 0.0930(4) 0.21920(15) 0.0454(5) Uani 1 1 d . . . . .
H2 H 0.302645 0.189620 0.217619 0.055 Uiso 1 1 calc R U . . .
C3 C 0.36862(9) 0.1504(5) 0.15008(15) 0.0485(6) Uani 1 1 d . . . . .
H3 H 0.356757 0.282457 0.102131 0.058 Uiso 1 1 calc R U . . .
C4 C 0.41842(8) 0.0118(4) 0.15261(14) 0.0411(5) Uani 1 1 d . . . . .
C5 C 0.43537(9) -0.1834(5) 0.22370(16) 0.0523(6) Uani 1 1 d . . . . .
H5 H 0.469446 -0.275959 0.226283 0.063 Uiso 1 1 calc R U . . .
C6 C 0.40223(9) -0.2428(4) 0.29105(16) 0.0491(6) Uani 1 1 d . . . . .
H6 H 0.413736 -0.378247 0.337702 0.059 Uiso 1 1 calc R U . . .
C7 C 0.43977(11) 0.2586(5) 0.01584(17) 0.0631(7) Uani 1 1 d . . . . .
H7A H 0.403074 0.220823 -0.026971 0.095 Uiso 1 1 calc R U . . .
H7B H 0.468401 0.266779 -0.023348 0.095 Uiso 1 1 calc R U . . .
H7C H 0.438157 0.427276 0.048697 0.095 Uiso 1 1 calc R U . . .
C8 C 0.31701(8) -0.1778(4) 0.36336(14) 0.0368(5) Uani 1 1 d . . . . .
C9 C 0.22774(8) 0.1850(4) 0.48445(13) 0.0355(5) Uani 1 1 d . . . . .
H9 H 0.228800 0.345871 0.450703 0.043 Uiso 1 1 calc R U . . .
C10 C 0.19599(8) 0.1678(4) 0.56459(13) 0.0316(4) Uani 1 1 d . . . . .
C11 C 0.21177(8) -0.0167(4) 0.64206(14) 0.0387(5) Uani 1 1 d . . . . .
H11 H 0.240802 -0.139415 0.640197 0.046 Uiso 1 1 calc R U . . .
C12 C 0.18496(9) -0.0203(4) 0.72161(14) 0.0447(5) Uani 1 1 d . . . . .
H12 H 0.195659 -0.145527 0.772518 0.054 Uiso 1 1 calc R U . . .
C13 C 0.14253(9) 0.1618(4) 0.72489(14) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.125288 0.162733 0.779371 0.054 Uiso 1 1 calc R U . . .
C14 C 0.12497(9) 0.3441(4) 0.64859(14) 0.0407(5) Uani 1 1 d . . . . .
H14 H 0.095792 0.465347 0.651231 0.049 Uiso 1 1 calc R U . . .
C15 C 0.15124(8) 0.3450(4) 0.56778(13) 0.0320(4) Uani 1 1 d . . . . .
C16 C 0.08874(8) 0.6892(4) 0.48332(14) 0.0371(5) Uani 1 1 d . . . . .
H16A H 0.098152 0.816194 0.538010 0.045 Uiso 1 1 calc R U . . .
H16B H 0.054534 0.591767 0.489305 0.045 Uiso 1 1 calc R U . . .
C17 C 0.07869(9) 0.8332(4) 0.38502(15) 0.0460(5) Uani 1 1 d . . . . .
H17A H 0.071300 0.702970 0.331239 0.055 Uiso 1 1 calc R U . . .
H17B H 0.113039 0.931803 0.380686 0.055 Uiso 1 1 calc R U . . .
C18 C 0.02849(10) 1.0259(5) 0.37195(17) 0.0587(6) Uani 1 1 d . . . . .
H18A H -0.005912 0.928113 0.373379 0.088 Uiso 1 1 calc R U . . .
H18B H 0.024022 1.116761 0.309025 0.088 Uiso 1 1 calc R U . . .
H18C H 0.035577 1.154927 0.425159 0.088 Uiso 1 1 calc R U . . .


_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
O1 C4 1.368(2) . ?
O1 C7 1.422(3) . ?
O2 C15 1.368(2) . ?
O2 C16 1.427(2) . ?
O3 C8 1.223(2) . ?
N1 C8 1.357(2) . ?
N1 N2 1.378(2) . ?
N1 H1 0.8600 . ?
N2 C9 1.272(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.384(3) . ?
C1 C8 1.486(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.470(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.500(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C4 O1 C7 118.07(17) . . ?
C15 O2 C16 118.35(14) . . ?
C8 N1 N2 119.88(16) . . ?
C8 N1 H1 120.1 . . ?
N2 N1 H1 120.1 . . ?
C9 N2 N1 115.20(16) . . ?
C2 C1 C6 117.66(18) . . ?
C2 C1 C8 123.09(17) . . ?
C6 C1 C8 119.22(18) . . ?
C1 C2 C3 121.69(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.64(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O1 C4 C3 124.76(19) . . ?
O1 C4 C5 115.67(18) . . ?
C3 C4 C5 119.58(18) . . ?
C4 C5 C6 120.42(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 N1 122.38(18) . . ?
O3 C8 C1 122.43(18) . . ?
N1 C8 C1 115.19(17) . . ?
N2 C9 C10 120.22(18) . . ?
N2 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C15 118.33(17) . . ?
C11 C10 C9 120.78(18) . . ?
C15 C10 C9 120.82(17) . . ?
C12 C11 C10 121.09(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.53(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.02(18) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.49(19) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
O2 C15 C14 124.12(17) . . ?
O2 C15 C10 115.37(15) . . ?
C14 C15 C10 120.49(17) . . ?
O2 C16 C17 107.32(15) . . ?
O2 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
O2 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 C18 112.04(17) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 178.77(17) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C8 C1 C2 C3 -177.63(19) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C7 O1 C4 C3 2.0(3) . . . . ?
C7 O1 C4 C5 -177.77(19) . . . . ?
C2 C3 C4 O1 -179.59(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
O1 C4 C5 C6 -179.2(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C8 C1 C6 C5 178.93(19) . . . . ?
N2 N1 C8 O3 1.5(3) . . . . ?
N2 N1 C8 C1 -178.50(15) . . . . ?
C2 C1 C8 O3 148.0(2) . . . . ?
C6 C1 C8 O3 -30.0(3) . . . . ?
C2 C1 C8 N1 -32.0(3) . . . . ?
C6 C1 C8 N1 150.05(19) . . . . ?
N1 N2 C9 C10 -173.95(16) . . . . ?
N2 C9 C10 C11 27.2(3) . . . . ?
N2 C9 C10 C15 -156.15(18) . . . . ?
C15 C10 C11 C12 -1.7(3) . . . . ?
C9 C10 C11 C12 175.02(18) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C16 O2 C15 C14 -0.1(2) . . . . ?
C16 O2 C15 C10 178.32(16) . . . . ?
C13 C14 C15 O2 176.74(18) . . . . ?
C13 C14 C15 C10 -1.6(3) . . . . ?
C11 C10 C15 O2 -175.66(16) . . . . ?
C9 C10 C15 O2 7.6(2) . . . . ?
C11 C10 C15 C14 2.8(3) . . . . ?
C9 C10 C15 C14 -173.97(17) . . . . ?
C15 O2 C16 C17 -177.55(15) . . . . ?
O2 C16 C17 C18 178.08(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.86 2.16 2.916(2) 146.1 1_565 yes
C7 H7A O3 0.96 2.64 3.530(3) 153.8 4 yes

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_MHA14AJK
_database_code_depnum_ccdc_archive 'CCDC 1963585'
loop_
_audit_author_name
_audit_author_address
'Dr.Muhammad Nawaz Tahir'
;University of sargodha
Pakistan
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
(E)-N'-(4-(?nyloxy)benzylidene)-2-phenylacetohydrazide
;
_chemical_formula_moiety         'C24 H32 N2 O2'
_chemical_formula_sum            'C24 H32 N2 O2'
_chemical_formula_iupac          'C24 H32 N2 O2'
_chemical_formula_weight         380.51

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   9.695(8)
_cell_length_b                   24.699(9)
_cell_length_c                   9.476(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2269(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1099
_cell_measurement_theta_min      3.117
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.965
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_mo?chromator   graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.833
_diffrn_reflns_number            10378
_diffrn_reflns_av_unetI/netI     0.1465
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.979
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is ?t relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             2195
_reflns_number_gt                1090
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      0.981
_refine_ls_number_reflns         2195
_refine_ls_number_parameters     293
_refine_ls_number_restraints     153
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0067(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.6439(3) 0.00603(13) -0.3193(4) 1.000 0.0613(12) . . . .
O2 O Uani 0.8971(4) 0.28362(15) 0.1811(4) 1.000 0.0797(16) . . . .
N1 N Uani 0.8632(4) 0.03627(15) -0.3130(4) 1.000 0.0510(14) . . . .
N2 N Uani 0.8363(4) 0.07623(16) -0.2138(4) 1.000 0.0490(16) . . . .
C1 C Uani 0.7179(5) -0.0826(2) -0.4973(5) 1.000 0.049(2) . . . .
C2 C Uani 0.7418(7) -0.1335(2) -0.4424(5) 1.000 0.065(2) . . . .
C3 C Uani 0.6567(8) -0.1765(3) -0.4737(8) 1.000 0.086(3) . . . .
C4 C Uani 0.5435(8) -0.1678(3) -0.5589(8) 1.000 0.088(3) . . . .
C5 C Uani 0.5150(7) -0.1173(3) -0.6098(7) 1.000 0.078(3) . . . .
C6 C Uani 0.6016(6) -0.0750(3) -0.5794(5) 1.000 0.060(2) . . . .
C7 C Uani 0.8150(6) -0.0369(2) -0.4678(5) 1.000 0.0617(19) . . . .
C8 C Uani 0.7627(5) 0.0028(2) -0.3603(5) 1.000 0.0490(17) . . . .
C9 C Uani 0.9338(5) 0.1095(2) -0.1933(5) 1.000 0.0510(17) . . . .
C10 C Uani 0.9205(5) 0.1534(2) -0.0929(5) 1.000 0.0490(19) . . . .
C11 C Uani 1.0088(6) 0.1980(2) -0.1024(6) 1.000 0.0623(19) . . . .
C12 C Uani 0.9965(6) 0.2402(2) -0.0094(6) 1.000 0.066(2) . . . .
C13 C Uani 0.8960(6) 0.2398(2) 0.0942(6) 1.000 0.058(2) . . . .
C14 C Uani 0.8102(6) 0.1961(2) 0.1063(5) 1.000 0.063(2) . . . .
C15 C Uani 0.8233(6) 0.1531(2) 0.0140(6) 1.000 0.058(2) . . . .
C16 C Uani 0.7884(7) 0.2880(2) 0.2819(7) 1.000 0.087(3) . . . .
C17 C Uani 0.8183(9) 0.3382(2) 0.3684(7) 1.000 0.112(3) . . . .
C18 C Uani 0.8197(9) 0.3883(3) 0.2875(9) 1.000 0.129(4) . . . .
C19A C Uani 0.842(7) 0.4386(8) 0.378(3) 0.464(15) 0.147(6) . . . .
C20A C Uani 0.863(6) 0.4863(8) 0.284(4) 0.464(15) 0.165(7) . . . .
C21A C Uani 0.823(4) 0.5384(8) 0.352(3) 0.464(15) 0.174(9) . . . .
C22A C Uani 0.847(4) 0.5839(8) 0.245(3) 0.464(15) 0.183(9) . . . .
C23A C Uani 0.797(4) 0.6351(8) 0.315(3) 0.464(15) 0.180(10) . . . .
C24A C Uani 0.806(4) 0.6803(13) 0.210(4) 0.464(15) 0.180(15) . . . .
C19B C Uani 0.872(7) 0.4373(9) 0.370(5) 0.369(13) 0.147(6) . . . .
C20B C Uani 0.852(8) 0.4923(10) 0.307(5) 0.369(13) 0.165(7) . . . .
C21B C Uani 0.902(5) 0.5375(10) 0.400(4) 0.369(13) 0.174(9) . . . .
C22B C Uani 0.901(3) 0.5927(10) 0.334(4) 0.369(13) 0.183(9) . . . .
C23B C Uani 0.775(4) 0.6074(11) 0.252(5) 0.369(13) 0.180(10) . . . .
C24B C Uani 0.758(5) 0.6678(12) 0.248(6) 0.369(13) 0.180(15) . . . .
C19C C Uani 0.808(15) 0.4393(11) 0.374(6) 0.167(15) 0.147(6) . . . .
C20C C Uani 0.793(11) 0.4898(13) 0.287(9) 0.167(15) 0.165(7) . . . .
C21C C Uani 0.864(10) 0.5369(18) 0.358(10) 0.167(15) 0.174(9) . . . .
C22C C Uani 0.801(7) 0.5898(17) 0.311(10) 0.167(15) 0.183(9) . . . .
C23C C Uani 0.909(7) 0.630(2) 0.269(8) 0.167(15) 0.180(10) . . . .
C24C C Uani 0.852(10) 0.672(4) 0.172(11) 0.167(15) 0.180(15) . . . .
H1 H Uiso 0.94557 0.03267 -0.34524 1.000 0.0609 . . . .
H18A H Uiso 0.73274 0.39181 0.23774 1.000 0.1544 . . . .
H2 H Uiso 0.81695 -0.13882 -0.38306 1.000 0.0780 . . . .
H18B H Uiso 0.89248 0.38628 0.21740 1.000 0.1544 . . . .
H3 H Uiso 0.67519 -0.21082 -0.43787 1.000 0.1036 . . . .
H19A H Uiso 0.76253 0.44446 0.43805 0.464(15) 0.1761 . . . .
H4 H Uiso 0.48602 -0.19665 -0.58194 1.000 0.1060 . . . .
H19B H Uiso 0.92237 0.43369 0.43748 0.464(15) 0.1761 . . . .
H5 H Uiso 0.43702 -0.11164 -0.66501 1.000 0.0937 . . . .
H20A H Uiso 0.80801 0.48151 0.19885 0.464(15) 0.1988 . . . .
H6 H Uiso 0.58179 -0.04067 -0.61443 1.000 0.0719 . . . .
H20B H Uiso 0.95881 0.48808 0.25599 0.464(15) 0.1988 . . . .
H21A H Uiso 0.87865 0.54439 0.43573 0.464(15) 0.2093 . . . .
H7A H Uiso 0.83296 -0.01769 -0.55521 1.000 0.0740 . . . .
H7B H Uiso 0.90183 -0.05169 -0.43483 1.000 0.0740 . . . .
H21B H Uiso 0.72686 0.53750 0.37966 0.464(15) 0.2093 . . . .
H9 H Uiso 1.01556 0.10566 -0.24370 1.000 0.0611 . . . .
H22A H Uiso 0.94471 0.58688 0.22283 0.464(15) 0.2201 . . . .
H22B H Uiso 0.79674 0.57697 0.15892 0.464(15) 0.2201 . . . .
H11 H Uiso 1.07623 0.19908 -0.17214 1.000 0.0750 . . . .
H23A H Uiso 0.70173 0.63040 0.34557 0.464(15) 0.2151 . . . .
H12 H Uiso 1.05654 0.26944 -0.01594 1.000 0.0792 . . . .
H23B H Uiso 0.85251 0.64326 0.39694 0.464(15) 0.2151 . . . .
H24A H Uiso 0.77333 0.71321 0.25303 0.464(15) 0.2704 . . . .
H14 H Uiso 0.74318 0.19532 0.17644 1.000 0.0758 . . . .
H24B H Uiso 0.89954 0.68479 0.18089 0.464(15) 0.2704 . . . .
H15 H Uiso 0.76554 0.12326 0.02392 1.000 0.0703 . . . .
H24C H Uiso 0.74929 0.67197 0.12970 0.464(15) 0.2704 . . . .
H19C H Uiso 0.82779 0.43701 0.46129 0.369(13) 0.1761 . . . .
H16A H Uiso 0.78611 0.25619 0.34198 1.000 0.1043 . . . .
H16B H Uiso 0.70007 0.29130 0.23461 1.000 0.1043 . . . .
H19D H Uiso 0.97009 0.43233 0.38531 0.369(13) 0.1761 . . . .
H17A H Uiso 0.74922 0.34119 0.44200 1.000 0.1335 . . . .
H17B H Uiso 0.90723 0.33382 0.41389 1.000 0.1335 . . . .
H20C H Uiso 0.75454 0.49758 0.28801 0.369(13) 0.1988 . . . .
H20D H Uiso 0.90044 0.49403 0.21760 0.369(13) 0.1988 . . . .
H21C H Uiso 0.99527 0.52932 0.42916 0.369(13) 0.2093 . . . .
H21D H Uiso 0.84480 0.53843 0.48374 0.369(13) 0.2093 . . . .
H22C H Uiso 0.91278 0.61930 0.40806 0.369(13) 0.2201 . . . .
H22D H Uiso 0.97965 0.59552 0.27137 0.369(13) 0.2201 . . . .
H23C H Uiso 0.69407 0.59117 0.29547 0.369(13) 0.2151 . . . .
H23D H Uiso 0.78213 0.59348 0.15642 0.369(13) 0.2151 . . . .
H24D H Uiso 0.67683 0.67687 0.19485 0.369(13) 0.2704 . . . .
H24E H Uiso 0.74950 0.68140 0.34216 0.369(13) 0.2704 . . . .
H24F H Uiso 0.83738 0.68370 0.20341 0.369(13) 0.2704 . . . .
H19E H Uiso 0.72854 0.43610 0.43618 0.167(15) 0.1761 . . . .
H19F H Uiso 0.88919 0.44272 0.43297 0.167(15) 0.1761 . . . .
H20E H Uiso 0.69547 0.49806 0.27547 0.167(15) 0.1988 . . . .
H20F H Uiso 0.83212 0.48388 0.19454 0.167(15) 0.1988 . . . .
H21E H Uiso 0.85616 0.53341 0.45931 0.167(15) 0.2093 . . . .
H21F H Uiso 0.96131 0.53647 0.33349 0.167(15) 0.2093 . . . .
H22E H Uiso 0.73990 0.58320 0.23158 0.167(15) 0.2201 . . . .
H22F H Uiso 0.74586 0.60453 0.38742 0.167(15) 0.2201 . . . .
H23E H Uiso 0.94506 0.64753 0.35306 0.167(15) 0.2151 . . . .
H23F H Uiso 0.98423 0.61150 0.22270 0.167(15) 0.2151 . . . .
H24G H Uiso 0.92323 0.69729 0.14757 0.167(15) 0.2704 . . . .
H24H H Uiso 0.81723 0.65506 0.08846 0.167(15) 0.2704 . . . .
H24I H Uiso 0.77810 0.69106 0.21870 0.167(15) 0.2704 . . . .


_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
O1 C8 1.218(6) . ?
O2 C13 1.360(7) . ?
O2 C16 1.426(8) . ?
N1 N2 1.388(6) . ?
N1 C8 1.354(6) . ?
N2 C9 1.268(6) . ?
C1 C2 1.380(7) . ?
C1 C6 1.383(7) . ?
C1 C7 1.496(7) . ?
N1 H1 0.8600 . ?
C19A C20A 1.49(4) . ?
C19A C18 1.53(3) . ?
C2 C3 1.377(9) . ?
C20A C21A 1.49(4) . ?
C3 C4 1.379(11) . ?
C21A C22A 1.53(3) . ?
C4 C5 1.366(10) . ?
C22A C23A 1.51(3) . ?
C5 C6 1.371(10) . ?
C23A C24A 1.50(4) . ?
C7 C8 1.502(7) . ?
C19B C20B 1.50(4) . ?
C19B C18 1.53(4) . ?
C20B C21B 1.50(5) . ?
C9 C10 1.448(7) . ?
C21B C22B 1.50(4) . ?
C10 C15 1.384(8) . ?
C10 C11 1.398(7) . ?
C22B C23B 1.49(5) . ?
C11 C12 1.370(8) . ?
C23B C24B 1.50(4) . ?
C12 C13 1.383(8) . ?
C13 C14 1.368(8) . ?
C19C C18 1.51(4) . ?
C19C C20C 1.50(7) . ?
C14 C15 1.382(7) . ?
C20C C21C 1.51(10) . ?
C21C C22C 1.51(8) . ?
C16 C17 1.514(8) . ?
C22C C23C 1.50(9) . ?
C17 C18 1.456(10) . ?
C23C C24C 1.49(12) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C2 H2 0.9300 . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C3 H3 0.9300 . ?
C21A H21B 0.9700 . ?
C21A H21A 0.9700 . ?
C4 H4 0.9300 . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C5 H5 0.9300 . ?
C23A H23B 0.9700 . ?
C23A H23A 0.9700 . ?
C6 H6 0.9300 . ?
C24A H24B 0.9500 . ?
C24A H24A 0.9600 . ?
C24A H24C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C9 H9 0.9300 . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C11 H11 0.9300 . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C12 H12 0.9300 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
C24B H24D 0.9600 . ?
C19C H19E 0.9700 . ?
C19C H19F 0.9700 . ?
C14 H14 0.9300 . ?
C20C H20E 0.9700 . ?
C20C H20F 0.9700 . ?
C15 H15 0.9300 . ?
C21C H21E 0.9700 . ?
C21C H21F 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?
C22C H22F 0.9700 . ?
C22C H22E 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C23C H23F 0.9700 . ?
C23C H23E 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C24C H24G 0.9600 . ?
C24C H24H 0.9600 . ?
C24C H24I 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
C13 O2 C16 117.4(4) . . ?
N2 N1 C8 121.6(4) . . ?
N1 N2 C9 115.1(4) . . ?
C2 C1 C6 118.2(5) . . ?
C2 C1 C7 120.7(5) . . ?
C6 C1 C7 121.1(5) . . ?
C8 N1 H1 119.00 . . ?
N2 N1 H1 119.00 . . ?
C20A C19A C18 109(2) . . ?
C1 C2 C3 121.4(6) . . ?
C19A C20A C21A 113(3) . . ?
C2 C3 C4 118.9(7) . . ?
C20A C21A C22A 108(2) . . ?
C3 C4 C5 120.7(7) . . ?
C21A C22A C23A 106(2) . . ?
C4 C5 C6 119.9(6) . . ?
C22A C23A C24A 108(2) . . ?
C1 C6 C5 120.9(6) . . ?
C1 C7 C8 114.0(4) . . ?
C20B C19B C18 118(4) . . ?
O1 C8 N1 122.3(4) . . ?
O1 C8 C7 125.3(5) . . ?
N1 C8 C7 112.3(4) . . ?
C19B C20B C21B 114(4) . . ?
N2 C9 C10 121.3(4) . . ?
C20B C21B C22B 115(3) . . ?
C11 C10 C15 117.9(5) . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 C15 122.5(5) . . ?
C21B C22B C23B 116(3) . . ?
C10 C11 C12 120.3(5) . . ?
C22B C23B C24B 110(3) . . ?
C11 C12 C13 120.8(5) . . ?
O2 C13 C12 114.7(5) . . ?
C12 C13 C14 119.6(5) . . ?
O2 C13 C14 125.6(5) . . ?
C20C C19C C18 114(5) . . ?
C13 C14 C15 119.9(5) . . ?
C19C C20C C21C 111(7) . . ?
C10 C15 C14 121.5(5) . . ?
C20C C21C C22C 111(7) . . ?
O2 C16 C17 106.5(5) . . ?
C21C C22C C23C 112(6) . . ?
C16 C17 C18 114.4(6) . . ?
C22C C23C C24C 112(6) . . ?
C19C C18 C17 115(2) . . ?
C19A C18 C17 113.4(11) . . ?
C19B C18 C17 114.0(16) . . ?
C20A C19A H19A 110.00 . . ?
C20A C19A H19B 110.00 . . ?
H19A C19A H19B 108.00 . . ?
C18 C19A H19A 110.00 . . ?
C18 C19A H19B 110.00 . . ?
C1 C2 H2 119.00 . . ?
C3 C2 H2 119.00 . . ?
C19A C20A H20B 109.00 . . ?
C21A C20A H20A 109.00 . . ?
C19A C20A H20A 109.00 . . ?
C21A C20A H20B 109.00 . . ?
H20A C20A H20B 108.00 . . ?
C2 C3 H3 121.00 . . ?
C4 C3 H3 121.00 . . ?
H21A C21A H21B 108.00 . . ?
C20A C21A H21A 110.00 . . ?
C20A C21A H21B 110.00 . . ?
C22A C21A H21A 110.00 . . ?
C22A C21A H21B 110.00 . . ?
C3 C4 H4 120.00 . . ?
C5 C4 H4 120.00 . . ?
C21A C22A H22A 110.00 . . ?
C21A C22A H22B 111.00 . . ?
C23A C22A H22A 110.00 . . ?
C23A C22A H22B 111.00 . . ?
H22A C22A H22B 109.00 . . ?
C6 C5 H5 120.00 . . ?
C4 C5 H5 120.00 . . ?
C22A C23A H23B 110.00 . . ?
C22A C23A H23A 110.00 . . ?
H23A C23A H23B 108.00 . . ?
C24A C23A H23A 110.00 . . ?
C24A C23A H23B 110.00 . . ?
C5 C6 H6 120.00 . . ?
C1 C6 H6 120.00 . . ?
H24A C24A H24C 109.00 . . ?
H24B C24A H24C 110.00 . . ?
H24A C24A H24B 110.00 . . ?
C23A C24A H24A 109.00 . . ?
C23A C24A H24B 110.00 . . ?
C23A C24A H24C 109.00 . . ?
C8 C7 H7A 109.00 . . ?
C1 C7 H7A 109.00 . . ?
C1 C7 H7B 109.00 . . ?
C8 C7 H7B 109.00 . . ?
H7A C7 H7B 108.00 . . ?
C20B C19B H19D 108.00 . . ?
H19C C19B H19D 107.00 . . ?
C20B C19B H19C 108.00 . . ?
C18 C19B H19C 108.00 . . ?
C18 C19B H19D 108.00 . . ?
C19B C20B H20D 109.00 . . ?
H20C C20B H20D 108.00 . . ?
C21B C20B H20C 109.00 . . ?
C21B C20B H20D 109.00 . . ?
C19B C20B H20C 109.00 . . ?
N2 C9 H9 119.00 . . ?
C10 C9 H9 119.00 . . ?
C20B C21B H21D 108.00 . . ?
C22B C21B H21C 108.00 . . ?
C20B C21B H21C 108.00 . . ?
H21C C21B H21D 108.00 . . ?
C22B C21B H21D 108.00 . . ?
C21B C22B H22D 108.00 . . ?
C21B C22B H22C 108.00 . . ?
C23B C22B H22C 108.00 . . ?
C23B C22B H22D 108.00 . . ?
H22C C22B H22D 108.00 . . ?
C10 C11 H11 120.00 . . ?
C12 C11 H11 120.00 . . ?
H23C C23B H23D 108.00 . . ?
C22B C23B H23C 110.00 . . ?
C22B C23B H23D 110.00 . . ?
C24B C23B H23C 109.00 . . ?
C24B C23B H23D 110.00 . . ?
C13 C12 H12 120.00 . . ?
C11 C12 H12 120.00 . . ?
C23B C24B H24F 109.00 . . ?
H24D C24B H24E 110.00 . . ?
C23B C24B H24E 110.00 . . ?
H24E C24B H24F 110.00 . . ?
H24D C24B H24F 109.00 . . ?
C23B C24B H24D 110.00 . . ?
C18 C19C H19E 109.00 . . ?
C20C C19C H19F 109.00 . . ?
C18 C19C H19F 109.00 . . ?
C20C C19C H19E 109.00 . . ?
H19E C19C H19F 108.00 . . ?
C13 C14 H14 120.00 . . ?
C15 C14 H14 120.00 . . ?
C19C C20C H20F 110.00 . . ?
C21C C20C H20E 109.00 . . ?
C19C C20C H20E 109.00 . . ?
H20E C20C H20F 108.00 . . ?
C21C C20C H20F 110.00 . . ?
C14 C15 H15 119.00 . . ?
C10 C15 H15 119.00 . . ?
C22C C21C H21F 109.00 . . ?
C20C C21C H21E 110.00 . . ?
H21E C21C H21F 108.00 . . ?
C22C C21C H21E 110.00 . . ?
C20C C21C H21F 109.00 . . ?
C17 C16 H16B 111.00 . . ?
C17 C16 H16A 110.00 . . ?
O2 C16 H16A 110.00 . . ?
O2 C16 H16B 110.00 . . ?
H16A C16 H16B 109.00 . . ?
C21C C22C H22E 109.00 . . ?
C23C C22C H22F 110.00 . . ?
H22E C22C H22F 108.00 . . ?
C23C C22C H22E 109.00 . . ?
C21C C22C H22F 109.00 . . ?
C18 C17 H17B 109.00 . . ?
C18 C17 H17A 109.00 . . ?
C16 C17 H17A 109.00 . . ?
H17A C17 H17B 108.00 . . ?
C16 C17 H17B 109.00 . . ?
C24C C23C H23F 109.00 . . ?
H23E C23C H23F 108.00 . . ?
C22C C23C H23E 109.00 . . ?
C22C C23C H23F 110.00 . . ?
C24C C23C H23E 109.00 . . ?
C19A C18 H18A 109.00 . . ?
C19A C18 H18B 109.00 . . ?
C19B C18 H18A 118.00 . . ?
C19B C18 H18B 99.00 . . ?
C19C C18 H18A 97.00 . . ?
C19C C18 H18B 118.00 . . ?
H18A C18 H18B 108.00 . . ?
C17 C18 H18A 109.00 . . ?
C17 C18 H18B 109.00 . . ?
C23C C24C H24G 110.00 . . ?
C23C C24C H24H 110.00 . . ?
C23C C24C H24I 109.00 . . ?
H24G C24C H24H 110.00 . . ?
H24G C24C H24I 109.00 . . ?
H24H C24C H24I 109.00 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 O2 C13 C12 174.5(5) . . . . no
C16 O2 C13 C14 -8.8(8) . . . . no
C13 O2 C16 C17 177.2(5) . . . . no
C8 N1 N2 C9 -170.5(4) . . . . no
N2 N1 C8 O1 0.4(7) . . . . no
N2 N1 C8 C7 179.6(4) . . . . no
N1 N2 C9 C10 180.0(4) . . . . no
C6 C1 C2 C3 3.3(8) . . . . no
C7 C1 C2 C3 -177.1(6) . . . . no
C2 C1 C6 C5 -2.4(8) . . . . no
C7 C1 C6 C5 178.0(5) . . . . no
C2 C1 C7 C8 -103.8(6) . . . . no
C6 C1 C7 C8 75.8(6) . . . . no
C1 C2 C3 C4 -1.7(10) . . . . no
C2 C3 C4 C5 -0.9(11) . . . . no
C3 C4 C5 C6 1.8(11) . . . . no
C4 C5 C6 C1 -0.2(9) . . . . no
C1 C7 C8 O1 -14.6(7) . . . . no
C1 C7 C8 N1 166.2(4) . . . . no
N2 C9 C10 C11 -160.7(5) . . . . no
N2 C9 C10 C15 19.6(8) . . . . no
C9 C10 C11 C12 179.2(5) . . . . no
C15 C10 C11 C12 -1.1(8) . . . . no
C9 C10 C15 C14 -178.3(5) . . . . no
C11 C10 C15 C14 2.0(8) . . . . no
C10 C11 C12 C13 -0.7(8) . . . . no
C11 C12 C13 O2 178.7(5) . . . . no
C11 C12 C13 C14 1.7(9) . . . . no
O2 C13 C14 C15 -177.5(5) . . . . no
C12 C13 C14 C15 -0.9(8) . . . . no
C13 C14 C15 C10 -1.0(8) . . . . no
O2 C16 C17 C18 61.9(8) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O1 0.8600 2.1600 2.916(5) 146.00 4_555 ?
C7 H7A O1 0.9700 2.5800 3.518(7) 163.00 3_654 ?


_refine_diff_density_max         0.13
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.032

