# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_Cu_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2141873'
loop_
_audit_author_name
_audit_author_address
'Nayarassery N. Adarsh'
;Chemistry and Biomolecular Science, Clarkson University
India
;
_audit_update_record             
;
2022-03-20 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 Cl Cu N5 O2'
_chemical_formula_weight         517.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.1305(7)
_cell_length_b                   9.2545(8)
_cell_length_c                   14.7289(13)
_cell_angle_alpha                96.831(3)
_cell_angle_beta                 98.583(3)
_cell_angle_gamma                104.865(3)
_cell_volume                     1044.74(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6450
_cell_measurement_theta_min      2.318
_cell_measurement_theta_max      27.188

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             526
_exptl_transmission_factor_min   0.780
_exptl_transmission_factor_max   0.885
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.210
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Microfocal D8 venture Bruker APEX 3'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_detector_area_resol_mean 3
_diffrn_reflns_number            36304
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         28.358
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5178
_reflns_number_gt                4790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+12.6854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5178
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.2316
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu01 Cu 0.36345(10) 0.18995(8) 0.58842(5) 0.0297(2) Uani 1 1 d . . . . .
Cl00 Cl 0.4768(3) 0.41864(19) 0.66975(14) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.2148(7) 0.2505(6) 0.4852(4) 0.0333(12) Uani 1 1 d . . . . .
O004 O 0.4682(7) 0.2539(7) 0.8566(4) 0.0532(15) Uani 1 1 d . . . . .
N3 N 0.4738(7) 0.0585(6) 0.6725(4) 0.0290(11) Uani 1 1 d . . . . .
O007 O 0.3060(9) -0.2451(6) 0.4834(4) 0.0597(17) Uani 1 1 d . . . . .
N4 N 0.7482(7) 0.3388(7) 0.8346(4) 0.0367(13) Uani 1 1 d . . . . .
H4 H 0.824196 0.308759 0.808600 0.044 Uiso 1 1 calc R U . . .
N2 N 0.2699(7) -0.0042(6) 0.5094(4) 0.0327(12) Uani 1 1 d . . . . .
N5 N 1.0760(8) 0.4873(7) 0.8405(4) 0.0385(13) Uani 1 1 d . . . . .
C9 C 0.1519(8) -0.0129(7) 0.4289(4) 0.0296(12) Uani 1 1 d . . . . .
C11 C 0.4451(8) -0.0830(7) 0.6253(4) 0.0310(13) Uani 1 1 d . . . . .
C10 C 0.3285(9) -0.1210(7) 0.5307(5) 0.0335(14) Uani 1 1 d . . . . .
C8 C 0.0609(9) -0.1378(7) 0.3633(5) 0.0372(15) Uani 1 1 d . . . . .
H8 H 0.075801 -0.232570 0.370048 0.045 Uiso 1 1 calc R U . . .
C5 C 0.1219(8) 0.1288(7) 0.4173(4) 0.0294(12) Uani 1 1 d . . . . .
C16 C 0.5895(9) 0.2382(8) 0.8193(5) 0.0363(14) Uani 1 1 d . . . . .
C15 C 0.5739(8) 0.0910(8) 0.7581(5) 0.0338(14) Uani 1 1 d . . . . .
C12 C 0.5125(10) -0.1906(8) 0.6591(5) 0.0383(15) Uani 1 1 d . . . . .
H12 H 0.486220 -0.287143 0.624476 0.046 Uiso 1 1 calc R U . . .
C17 C 0.8057(9) 0.4840(8) 0.8865(5) 0.0340(14) Uani 1 1 d . . . . .
C1 C 0.1991(11) 0.3873(8) 0.4748(6) 0.0453(18) Uani 1 1 d . . . . .
H1 H 0.264048 0.470004 0.519343 0.054 Uiso 1 1 calc R U . . .
C6 C -0.0828(9) 0.0146(9) 0.2746(5) 0.0424(16) Uani 1 1 d . . . . .
H6 H -0.161067 0.021840 0.223620 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6214(10) -0.1545(9) 0.7461(5) 0.0429(17) Uani 1 1 d . . . . .
H13 H 0.671569 -0.224831 0.770199 0.051 Uiso 1 1 calc R U . . .
C4 C 0.0065(9) 0.1447(8) 0.3400(5) 0.0349(14) Uani 1 1 d . . . . .
C3 C -0.0080(10) 0.2908(9) 0.3344(6) 0.0464(18) Uani 1 1 d . . . . .
H3 H -0.084893 0.305818 0.285408 0.056 Uiso 1 1 calc R U . . .
C7 C -0.0555(10) -0.1225(9) 0.2855(5) 0.0423(17) Uani 1 1 d . . . . .
H7 H -0.114347 -0.207308 0.241040 0.051 Uiso 1 1 calc R U . . .
C14 C 0.6518(10) -0.0109(9) 0.7950(5) 0.0445(17) Uani 1 1 d . . . . .
H14 H 0.724901 0.017600 0.852880 0.053 Uiso 1 1 calc R U . . .
C21 C 1.0534(9) 0.7109(8) 0.9397(5) 0.0377(15) Uani 1 1 d . . . . .
C22 C 0.9825(9) 0.5630(8) 0.8884(5) 0.0349(14) Uani 1 1 d . . . . .
C18 C 0.7057(10) 0.5546(9) 0.9351(5) 0.0409(16) Uani 1 1 d . . . . .
H18 H 0.590023 0.505074 0.933430 0.049 Uiso 1 1 calc R U . . .
C23 C 1.2289(11) 0.7816(9) 0.9384(6) 0.0488(19) Uani 1 1 d . . . . .
H23 H 1.281120 0.880393 0.968941 0.059 Uiso 1 1 calc R U . . .
C20 C 0.9484(11) 0.7790(9) 0.9873(6) 0.0486(19) Uani 1 1 d . . . . .
H20 H 0.992595 0.877619 1.019539 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7792(11) 0.6993(9) 0.9861(6) 0.0466(18) Uani 1 1 d . . . . .
H19 H 0.712484 0.743726 1.020406 0.056 Uiso 1 1 calc R U . . .
C24 C 1.3202(11) 0.7049(10) 0.8926(6) 0.053(2) Uani 1 1 d . . . . .
H24 H 1.436951 0.749123 0.893307 0.064 Uiso 1 1 calc R U . . .
C2 C 0.0885(12) 0.4115(9) 0.3996(6) 0.056(2) Uani 1 1 d . . . . .
H2 H 0.080990 0.508723 0.394010 0.067 Uiso 1 1 calc R U . . .
C25 C 1.2389(10) 0.5590(10) 0.8442(6) 0.0472(18) Uani 1 1 d . . . . .
H25 H 1.304522 0.509207 0.812391 0.057 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
Cu01 N2 1.923(5) . ?
Cu01 N1 2.022(6) . ?
Cu01 N3 2.099(5) . ?
Cu01 Cl00 2.1978(18) . ?
N1 C1 1.329(9) . ?
N1 C5 1.382(8) . ?
O004 C16 1.230(9) . ?
N3 C15 1.349(8) . ?
N3 C11 1.353(8) . ?
O007 C10 1.225(8) . ?
N4 C16 1.352(9) . ?
N4 C17 1.391(8) . ?
N4 H4 0.8600 . ?
N2 C10 1.339(8) . ?
N2 C9 1.390(8) . ?
N5 C25 1.310(10) . ?
N5 C22 1.372(9) . ?
C9 C8 1.378(8) . ?
C9 C5 1.419(9) . ?
C11 C12 1.362(9) . ?
C11 C10 1.511(9) . ?
C8 C7 1.419(10) . ?
C8 H8 0.9300 . ?
C5 C4 1.410(9) . ?
C16 C15 1.506(9) . ?
C15 C14 1.383(10) . ?
C12 C13 1.395(10) . ?
C12 H12 0.9300 . ?
C17 C18 1.391(10) . ?
C17 C22 1.430(9) . ?
C1 C2 1.397(11) . ?
C1 H1 0.9300 . ?
C6 C7 1.366(11) . ?
C6 C4 1.404(10) . ?
C6 H6 0.9300 . ?
C13 C14 1.377(11) . ?
C13 H13 0.9300 . ?
C4 C3 1.398(10) . ?
C3 C2 1.362(11) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C14 H14 0.9300 . ?
C21 C20 1.402(11) . ?
C21 C22 1.413(9) . ?
C21 C23 1.413(11) . ?
C18 C19 1.390(10) . ?
C18 H18 0.9300 . ?
C23 C24 1.347(13) . ?
C23 H23 0.9300 . ?
C20 C19 1.381(12) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C24 C25 1.393(12) . ?
C24 H24 0.9300 . ?
C2 H2 0.9300 . ?
C25 H25 0.9300 . ?

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
N2 Cu01 N1 81.1(2) . . ?
N2 Cu01 N3 81.0(2) . . ?
N1 Cu01 N3 161.8(2) . . ?
N2 Cu01 Cl00 175.77(19) . . ?
N1 Cu01 Cl00 96.44(16) . . ?
N3 Cu01 Cl00 101.67(15) . . ?
C1 N1 C5 118.4(6) . . ?
C1 N1 Cu01 129.0(5) . . ?
C5 N1 Cu01 112.6(4) . . ?
C15 N3 C11 116.7(6) . . ?
C15 N3 Cu01 132.9(4) . . ?
C11 N3 Cu01 110.2(4) . . ?
C16 N4 C17 129.1(6) . . ?
C16 N4 H4 115.4 . . ?
C17 N4 H4 115.4 . . ?
C10 N2 C9 123.2(5) . . ?
C10 N2 Cu01 119.3(4) . . ?
C9 N2 Cu01 117.4(4) . . ?
C25 N5 C22 116.7(7) . . ?
C8 C9 N2 129.1(6) . . ?
C8 C9 C5 118.1(6) . . ?
N2 C9 C5 112.8(5) . . ?
N3 C11 C12 123.7(6) . . ?
N3 C11 C10 116.7(6) . . ?
C12 C11 C10 119.6(6) . . ?
O007 C10 N2 129.2(6) . . ?
O007 C10 C11 118.9(6) . . ?
N2 C10 C11 111.8(5) . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
N1 C5 C4 122.1(6) . . ?
N1 C5 C9 116.0(6) . . ?
C4 C5 C9 121.9(6) . . ?
O004 C16 N4 125.4(7) . . ?
O004 C16 C15 120.0(6) . . ?
N4 C16 C15 114.3(6) . . ?
N3 C15 C14 122.4(6) . . ?
N3 C15 C16 119.0(6) . . ?
C14 C15 C16 118.3(6) . . ?
C11 C12 C13 119.3(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
N4 C17 C18 125.2(6) . . ?
N4 C17 C22 115.5(6) . . ?
C18 C17 C22 119.3(6) . . ?
N1 C1 C2 122.5(7) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C7 C6 C4 120.4(7) . . ?
C7 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
C14 C13 C12 117.6(7) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C3 C4 C6 125.1(7) . . ?
C3 C4 C5 116.7(6) . . ?
C6 C4 C5 118.1(6) . . ?
C2 C3 C4 121.1(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C6 C7 C8 121.2(6) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C13 C14 C15 120.1(7) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C20 C21 C22 119.4(7) . . ?
C20 C21 C23 124.1(7) . . ?
C22 C21 C23 116.5(7) . . ?
N5 C22 C21 123.3(7) . . ?
N5 C22 C17 116.9(6) . . ?
C21 C22 C17 119.8(7) . . ?
C19 C18 C17 119.8(7) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C24 C23 C21 119.6(8) . . ?
C24 C23 H23 120.2 . . ?
C21 C23 H23 120.2 . . ?
C19 C20 C21 119.8(7) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C19 C18 121.8(7) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C23 C24 C25 119.7(8) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C3 C2 C1 119.1(7) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N5 C25 C24 124.2(8) . . ?
N5 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?

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
C10 N2 C9 C8 7.7(11) . . . . ?
Cu01 N2 C9 C8 -176.8(6) . . . . ?
C10 N2 C9 C5 -174.3(6) . . . . ?
Cu01 N2 C9 C5 1.2(7) . . . . ?
C15 N3 C11 C12 -0.7(10) . . . . ?
Cu01 N3 C11 C12 174.7(6) . . . . ?
C15 N3 C11 C10 178.2(6) . . . . ?
Cu01 N3 C11 C10 -6.4(7) . . . . ?
C9 N2 C10 O007 7.4(13) . . . . ?
Cu01 N2 C10 O007 -168.0(7) . . . . ?
C9 N2 C10 C11 -175.9(6) . . . . ?
Cu01 N2 C10 C11 8.7(8) . . . . ?
N3 C11 C10 O007 176.3(7) . . . . ?
C12 C11 C10 O007 -4.7(11) . . . . ?
N3 C11 C10 N2 -0.7(9) . . . . ?
C12 C11 C10 N2 178.2(6) . . . . ?
N2 C9 C8 C7 179.6(7) . . . . ?
C5 C9 C8 C7 1.7(10) . . . . ?
C1 N1 C5 C4 -2.7(10) . . . . ?
Cu01 N1 C5 C4 178.4(5) . . . . ?
C1 N1 C5 C9 176.2(7) . . . . ?
Cu01 N1 C5 C9 -2.8(7) . . . . ?
C8 C9 C5 N1 179.4(6) . . . . ?
N2 C9 C5 N1 1.2(8) . . . . ?
C8 C9 C5 C4 -1.7(10) . . . . ?
N2 C9 C5 C4 -180.0(6) . . . . ?
C17 N4 C16 O004 -6.7(13) . . . . ?
C17 N4 C16 C15 179.4(7) . . . . ?
C11 N3 C15 C14 3.3(10) . . . . ?
Cu01 N3 C15 C14 -170.9(5) . . . . ?
C11 N3 C15 C16 -171.3(6) . . . . ?
Cu01 N3 C15 C16 14.5(9) . . . . ?
O004 C16 C15 N3 74.0(9) . . . . ?
N4 C16 C15 N3 -111.7(7) . . . . ?
O004 C16 C15 C14 -100.8(9) . . . . ?
N4 C16 C15 C14 73.5(9) . . . . ?
N3 C11 C12 C13 -1.7(11) . . . . ?
C10 C11 C12 C13 179.4(7) . . . . ?
C16 N4 C17 C18 0.7(12) . . . . ?
C16 N4 C17 C22 -179.5(7) . . . . ?
C5 N1 C1 C2 2.0(12) . . . . ?
Cu01 N1 C1 C2 -179.3(7) . . . . ?
C11 C12 C13 C14 1.6(11) . . . . ?
C7 C6 C4 C3 178.2(8) . . . . ?
C7 C6 C4 C5 -1.0(11) . . . . ?
N1 C5 C4 C3 0.9(10) . . . . ?
C9 C5 C4 C3 -177.9(7) . . . . ?
N1 C5 C4 C6 -179.8(6) . . . . ?
C9 C5 C4 C6 1.4(10) . . . . ?
C6 C4 C3 C2 -177.6(9) . . . . ?
C5 C4 C3 C2 1.6(12) . . . . ?
C4 C6 C7 C8 1.0(12) . . . . ?
C9 C8 C7 C6 -1.3(12) . . . . ?
C12 C13 C14 C15 0.8(11) . . . . ?
N3 C15 C14 C13 -3.4(11) . . . . ?
C16 C15 C14 C13 171.2(7) . . . . ?
C25 N5 C22 C21 0.3(10) . . . . ?
C25 N5 C22 C17 -178.6(7) . . . . ?
C20 C21 C22 N5 -179.5(7) . . . . ?
C23 C21 C22 N5 1.1(10) . . . . ?
C20 C21 C22 C17 -0.7(10) . . . . ?
C23 C21 C22 C17 179.9(7) . . . . ?
N4 C17 C22 N5 -0.8(9) . . . . ?
C18 C17 C22 N5 179.1(7) . . . . ?
N4 C17 C22 C21 -179.6(6) . . . . ?
C18 C17 C22 C21 0.2(10) . . . . ?
N4 C17 C18 C19 178.7(7) . . . . ?
C22 C17 C18 C19 -1.1(11) . . . . ?
C20 C21 C23 C24 178.2(8) . . . . ?
C22 C21 C23 C24 -2.5(11) . . . . ?
C22 C21 C20 C19 2.1(12) . . . . ?
C23 C21 C20 C19 -178.5(8) . . . . ?
C21 C20 C19 C18 -3.2(13) . . . . ?
C17 C18 C19 C20 2.7(13) . . . . ?
C21 C23 C24 C25 2.4(13) . . . . ?
C4 C3 C2 C1 -2.3(15) . . . . ?
N1 C1 C2 C3 0.5(15) . . . . ?
C22 N5 C25 C24 -0.4(12) . . . . ?
C23 C24 C25 N5 -0.9(13) . . . . ?

_refine_diff_density_max         2.055
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.147

####################################################################### 
# 
# 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_atoap30_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2143447'
loop_
_audit_author_name
_audit_author_address
'Nayarassery N. Adarsh'
;Chemistry and Biomolecular Science, Clarkson University
India
;
_audit_update_record             
;
2022-03-20 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2022-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_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'
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                   10.881(2)
_cell_length_b                   10.233(2)
_cell_length_c                   11.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.43(3)
_cell_angle_gamma                90
_cell_volume                     1163.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.783029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.3360 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.7830.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.290
_diffrn_reflns_theta_min         1.973
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'phi-omega scan'
_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                1902
_reflns_number_total             2604
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+0.3406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1735
_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 O(H) groups
2. Restrained distances
 O10-C8 \\sim O10B-C8
 with sigma of 0.01
3. Restrained planarity
 C11, C12, C13, C14
 with sigma of 0.01
 C11B, C12B, C13B, C14B
 with sigma of 0.01
4. Rigid bond restraints
 O10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Same fragment restrains
{O10, C11, C12, C13, C14, C15, C16} sigma for 1-2: 0.01, 1-3: 0.04
as in
{O10B, C11B, C12B, C13B, C14B, C15B, C16B}
7. Others
 Sof(O10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=
 Sof(C14B)=Sof(H14C)=Sof(H14D)=Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=
 Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C11(H11), C11B(H11B)
8.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C14B(H14C,H14D), C15B(H15C,
 H15D), C16B(H16C,H16D)
8.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C12B(H12B), C13B(H13B)
8.d Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_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
O1 O -0.10953(15) 0.79078(17) 0.50804(14) 0.0750(5) Uani 1 1 d . . . . .
H1 H -0.160584 0.805800 0.547380 0.112 Uiso 1 1 calc R U . . .
C2 C -0.01955(18) 0.70396(19) 0.57435(18) 0.0539(5) Uani 1 1 d . . . . .
C3 C 0.0757(2) 0.6673(2) 0.52153(19) 0.0612(5) Uani 1 1 d . . . . .
H3 H 0.075640 0.702159 0.443564 0.073 Uiso 1 1 calc R U . . .
C4 C 0.16934(18) 0.5799(2) 0.58436(18) 0.0570(5) Uani 1 1 d . . . . .
H4 H 0.232895 0.556393 0.548502 0.068 Uiso 1 1 calc R U . . .
C5 C 0.17157(16) 0.52545(19) 0.70077(16) 0.0493(4) Uani 1 1 d . . . . .
C6 C 0.07516(17) 0.56250(19) 0.75279(17) 0.0528(5) Uani 1 1 d . . . . .
H6 H 0.074539 0.526869 0.830252 0.063 Uiso 1 1 calc R U . . .
C7 C -0.01892(17) 0.65112(19) 0.69069(17) 0.0538(5) Uani 1 1 d . . . . .
H7 H -0.082095 0.675628 0.726666 0.065 Uiso 1 1 calc R U . . .
C8 C 0.27238(17) 0.43144(19) 0.76850(18) 0.0537(5) Uani 1 1 d D . . . .
O9 O 0.27346(13) 0.36952(16) 0.86284(14) 0.0699(5) Uani 1 1 d . . . . .
O10 O 0.3606(5) 0.4177(6) 0.7084(6) 0.0619(12) Uani 0.711(11) 1 d D U P A 1
C11 C 0.4711(5) 0.3293(4) 0.7682(6) 0.063(2) Uani 0.711(11) 1 d D . P A 1
H11 H 0.441269 0.255059 0.807599 0.076 Uiso 0.711(11) 1 calc R U P A 1
C12 C 0.5741(9) 0.3970(8) 0.8643(7) 0.090(3) Uani 0.711(11) 1 d D . P A 1
H12 H 0.563177 0.413960 0.943241 0.108 Uiso 0.711(11) 1 calc R U P A 1
C13 C 0.6865(6) 0.4372(6) 0.8450(6) 0.0936(19) Uani 0.711(11) 1 d D . P A 1
H13 H 0.749714 0.480156 0.909730 0.112 Uiso 0.711(11) 1 calc R U P A 1
C14 C 0.7074(8) 0.4110(9) 0.7165(10) 0.131(4) Uani 0.711(11) 1 d D . P A 1
H14A H 0.742070 0.489130 0.689499 0.157 Uiso 0.711(11) 1 calc R U P A 1
H14B H 0.770960 0.341916 0.727070 0.157 Uiso 0.711(11) 1 calc R U P A 1
C15 C 0.5913(6) 0.3741(7) 0.6192(5) 0.0902(17) Uani 0.711(11) 1 d D . P A 1
H15A H 0.539232 0.451736 0.589710 0.108 Uiso 0.711(11) 1 calc R U P A 1
H15B H 0.613827 0.338926 0.547254 0.108 Uiso 0.711(11) 1 calc R U P A 1
C16 C 0.5156(8) 0.2811(7) 0.6579(7) 0.093(4) Uani 0.711(11) 1 d D . P A 1
H16A H 0.565806 0.201704 0.683932 0.111 Uiso 0.711(11) 1 calc R U P A 1
H16B H 0.440182 0.259823 0.585702 0.111 Uiso 0.711(11) 1 calc R U P A 1
O10B O 0.3783(13) 0.4316(17) 0.7336(18) 0.088(6) Uani 0.289(11) 1 d D . P A 2
C11B C 0.4804(13) 0.3290(14) 0.7742(16) 0.111(10) Uani 0.289(11) 1 d D . P A 2
H11B H 0.453282 0.259233 0.821118 0.133 Uiso 0.289(11) 1 calc R U P A 2
C12B C 0.5124(13) 0.2757(12) 0.6652(14) 0.065(7) Uani 0.289(11) 1 d D . P A 2
H12B H 0.455099 0.217263 0.611226 0.078 Uiso 0.289(11) 1 calc R U P A 2
C13B C 0.6245(12) 0.3086(12) 0.6390(11) 0.088(4) Uani 0.289(11) 1 d D . P A 2
H13B H 0.642880 0.273274 0.568899 0.106 Uiso 0.289(11) 1 calc R U P A 2
C14B C 0.7177(7) 0.4049(11) 0.7288(14) 0.058(4) Uani 0.289(11) 1 d D . P A 2
H14C H 0.788507 0.356352 0.787281 0.070 Uiso 0.289(11) 1 calc R U P A 2
H14D H 0.754100 0.461795 0.678561 0.070 Uiso 0.289(11) 1 calc R U P A 2
C15B C 0.6581(15) 0.4822(14) 0.8004(13) 0.088(4) Uani 0.289(11) 1 d D . P A 2
H15C H 0.724692 0.532130 0.862570 0.105 Uiso 0.289(11) 1 calc R U P A 2
H15D H 0.600545 0.543966 0.743035 0.105 Uiso 0.289(11) 1 calc R U P A 2
C16B C 0.5870(17) 0.4120(16) 0.8653(16) 0.075(7) Uani 0.289(11) 1 d D . P A 2
H16C H 0.548323 0.472893 0.910100 0.090 Uiso 0.289(11) 1 calc R U P A 2
H16D H 0.645352 0.355646 0.928456 0.090 Uiso 0.289(11) 1 calc R U P A 2


_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 H1 0.8200 . ?
O1 C2 1.352(2) . ?
C2 C3 1.391(3) . ?
C2 C7 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(2) . ?
C5 C6 1.397(3) . ?
C5 C8 1.472(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(3) . ?
C7 H7 0.9300 . ?
C8 O9 1.214(2) . ?
C8 O10 1.336(4) . ?
C8 O10B 1.325(7) . ?
O10 C11 1.482(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.451(9) . ?
C11 C16 1.525(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.527(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.425(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.410(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O10B C11B 1.490(8) . ?
C11B H11B 0.9800 . ?
C11B C12B 1.458(13) . ?
C11B C16B 1.529(12) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.381(13) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.531(14) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C14B C15B 1.411(14) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C15B C16B 1.405(13) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C3 117.32(17) . . ?
O1 C2 C7 123.07(17) . . ?
C7 C2 C3 119.61(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.94(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.41(17) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.21(18) . . ?
C4 C5 C8 121.45(16) . . ?
C6 C5 C8 120.33(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.77(17) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.06(17) . . ?
C6 C7 H7 120.0 . . ?
O9 C8 C5 125.37(17) . . ?
O9 C8 O10 123.8(3) . . ?
O9 C8 O10B 118.3(7) . . ?
O10 C8 C5 110.8(3) . . ?
O10B C8 C5 115.4(6) . . ?
C8 O10 C11 116.9(5) . . ?
O10 C11 H11 109.5 . . ?
O10 C11 C16 105.1(5) . . ?
C12 C11 O10 111.3(5) . . ?
C12 C11 H11 109.6 . . ?
C12 C11 C16 111.7(5) . . ?
C16 C11 H11 109.5 . . ?
C11 C12 H12 118.3 . . ?
C13 C12 C11 123.4(6) . . ?
C13 C12 H12 118.3 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(6) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.8(6) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.5(6) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C11 C16 H16A 109.1 . . ?
C11 C16 H16B 109.1 . . ?
C15 C16 C11 112.7(6) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C8 O10B C11B 123.1(11) . . ?
O10B C11B H11B 110.6 . . ?
O10B C11B C16B 98.3(12) . . ?
C12B C11B O10B 111.5(12) . . ?
C12B C11B H11B 110.6 . . ?
C12B C11B C16B 114.8(11) . . ?
C16B C11B H11B 110.6 . . ?
C11B C12B H12B 118.7 . . ?
C13B C12B C11B 122.5(12) . . ?
C13B C12B H12B 118.8 . . ?
C12B C13B H13B 121.0 . . ?
C12B C13B C14B 118.1(10) . . ?
C14B C13B H13B 121.0 . . ?
C13B C14B H14C 108.9 . . ?
C13B C14B H14D 108.9 . . ?
H14C C14B H14D 107.7 . . ?
C15B C14B C13B 113.2(8) . . ?
C15B C14B H14C 108.9 . . ?
C15B C14B H14D 108.9 . . ?
C14B C15B H15C 108.5 . . ?
C14B C15B H15D 108.5 . . ?
H15C C15B H15D 107.5 . . ?
C16B C15B C14B 114.9(13) . . ?
C16B C15B H15C 108.5 . . ?
C16B C15B H15D 108.5 . . ?
C11B C16B H16C 109.2 . . ?
C11B C16B H16D 109.2 . . ?
C15B C16B C11B 112.1(13) . . ?
C15B C16B H16C 109.2 . . ?
C15B C16B H16D 109.2 . . ?
H16C C16B H16D 107.9 . . ?

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
O1 C2 C3 C4 179.92(19) . . . . ?
O1 C2 C7 C6 179.59(18) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C8 -179.97(19) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C4 C5 C8 O9 -171.8(2) . . . . ?
C4 C5 C8 O10 5.0(4) . . . . ?
C4 C5 C8 O10B 19.0(11) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C5 C8 O10 C11 177.9(4) . . . . ?
C5 C8 O10B C11B -169.1(13) . . . . ?
C6 C5 C8 O9 8.3(3) . . . . ?
C6 C5 C8 O10 -174.8(4) . . . . ?
C6 C5 C8 O10B -160.8(11) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C8 C5 C6 C7 179.48(17) . . . . ?
C8 O10 C11 C12 -85.4(7) . . . . ?
C8 O10 C11 C16 153.5(6) . . . . ?
C8 O10B C11B C12B 129.4(18) . . . . ?
C8 O10B C11B C16B -109.8(19) . . . . ?
O9 C8 O10 C11 -5.2(8) . . . . ?
O9 C8 O10B C11B 21(2) . . . . ?
O10 C11 C12 C13 -103.8(5) . . . . ?
O10 C11 C16 C15 78.5(7) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C11 C16 C15 -42.4(9) . . . . ?
C12 C13 C14 C15 14.3(7) . . . . ?
C13 C14 C15 C16 -44.8(9) . . . . ?
C14 C15 C16 C11 60.3(10) . . . . ?
C16 C11 C12 C13 13.3(6) . . . . ?
O10B C11B C12B C13B 104.2(11) . . . . ?
O10B C11B C16B C15B -84.4(16) . . . . ?
C11B C12B C13B C14B 0.0(3) . . . . ?
C12B C11B C16B C15B 33.9(19) . . . . ?
C12B C13B C14B C15B -20.9(10) . . . . ?
C13B C14B C15B C16B 50.9(17) . . . . ?
C14B C15B C16B C11B -58(2) . . . . ?
C16B C11B C12B C13B -6.4(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
