# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_wh1
_database_code_depnum_ccdc_archive 'CCDC 2023450'
loop_
_audit_author_name
_audit_author_address
Sudhadevi
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H32'
_chemical_formula_weight         512.65

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'

_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                   10.4475(5)
_cell_length_b                   12.2806(5)
_cell_length_c                   12.3903(7)
_cell_angle_alpha                100.338(2)
_cell_angle_beta                 99.001(3)
_cell_angle_gamma                104.084(2)
_cell_volume                     1483.14(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2394
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      21.75

_exptl_crystal_description       BLock
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19603
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.755
_diffrn_reflns_theta_max         24.888
_diffrn_reflns_theta_full        24.888
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5144
_reflns_number_gt                2908
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0521P)²+0.1937P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0080(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5144
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
C1 C 0.5670(2) 0.40278(17) 1.04660(18) 0.0480(5) Uani 1 1 d . . . . .
H1 H 0.6209 0.4733 1.0910 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4507(2) 0.34382(17) 1.08633(17) 0.0507(6) Uani 1 1 d . . . . .
H2 H 0.3843 0.3813 1.0952 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4319(2) 0.23996(17) 1.11102(17) 0.0461(5) Uani 1 1 d . . . . .
C4 C 0.5396(2) 0.17982(16) 1.10912(18) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.5721(2) 0.13903(17) 1.01231(18) 0.0473(5) Uani 1 1 d . . . . .
H5 H 0.6377 0.0996 1.0161 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5141(2) 0.15103(18) 0.90204(18) 0.0482(5) Uani 1 1 d . . . . .
H6 H 0.4694 0.0837 0.8480 0.058 Uiso 1 1 calc R U . . .
C7 C 0.51992(19) 0.25142(17) 0.87205(17) 0.0438(5) Uani 1 1 d . . . . .
C8 C 0.6018(2) 0.36279(16) 0.95093(17) 0.0438(5) Uani 1 1 d . . . . .
C9 C 0.3024(2) 0.17943(19) 1.13185(17) 0.0496(6) Uani 1 1 d . . . . .
H9 H 0.2401 0.2210 1.1419 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2672(2) 0.06963(19) 1.13740(17) 0.0490(5) Uani 1 1 d . . . . .
H10 H 0.3359 0.0335 1.1390 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1342(2) -0.00246(19) 1.14138(17) 0.0487(5) Uani 1 1 d . . . . .
C12 C 0.0248(2) 0.0397(2) 1.1545(2) 0.0642(7) Uani 1 1 d . . . . .
H12 H 0.0339 0.1181 1.1623 0.077 Uiso 1 1 calc R U . . .
C13 C -0.0981(2) -0.0341(3) 1.1560(2) 0.0804(8) Uani 1 1 d . . . . .
H13 H -0.1710 -0.0047 1.1642 0.097 Uiso 1 1 calc R U . . .
C14 C -0.1137(3) -0.1499(3) 1.1457(2) 0.0793(8) Uani 1 1 d . . . . .
H14 H -0.1964 -0.1985 1.1479 0.095 Uiso 1 1 calc R U . . .
C15 C -0.0076(3) -0.1933(2) 1.1321(2) 0.0699(7) Uani 1 1 d . . . . .
H15 H -0.0177 -0.2718 1.1247 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1148(2) -0.1206(2) 1.12936(18) 0.0577(6) Uani 1 1 d . . . . .
H16 H 0.1863 -0.1513 1.1192 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6100(2) 0.16105(17) 1.21220(18) 0.0480(6) Uani 1 1 d . . . . .
H17 H 0.6788 0.1264 1.2038 0.058 Uiso 1 1 calc R U . . .
C18 C 0.5914(2) 0.18570(18) 1.31623(19) 0.0547(6) Uani 1 1 d . . . . .
H18 H 0.5253 0.2223 1.3296 0.066 Uiso 1 1 calc R U . . .
C19 C 0.6704(2) 0.15787(19) 1.41149(19) 0.0569(6) Uani 1 1 d . . . . .
C20 C 0.6163(3) 0.1383(2) 1.5029(2) 0.0745(8) Uani 1 1 d . . . . .
H20 H 0.5333 0.1512 1.5087 0.089 Uiso 1 1 calc R U . . .
C21 C 0.6848(4) 0.0993(2) 1.5867(2) 0.0894(9) Uani 1 1 d . . . . .
H21 H 0.6457 0.0836 1.6467 0.107 Uiso 1 1 calc R U . . .
C22 C 0.8086(4) 0.0840(2) 1.5815(3) 0.0923(10) Uani 1 1 d . . . . .
H22 H 0.8533 0.0567 1.6372 0.111 Uiso 1 1 calc R U . . .
C23 C 0.8667(3) 0.1087(3) 1.4950(3) 0.1018(10) Uani 1 1 d . . . . .
H23 H 0.9524 0.1004 1.4924 0.122 Uiso 1 1 calc R U . . .
C24 C 0.7986(3) 0.1460(2) 1.4110(2) 0.0809(8) Uani 1 1 d . . . . .
H24 H 0.8398 0.1637 1.3526 0.097 Uiso 1 1 calc R U . . .
C25 C 0.7236(2) 0.42747(17) 0.92128(19) 0.0482(6) Uani 1 1 d . . . . .
H25 H 0.7720 0.4973 0.9702 0.058 Uiso 1 1 calc R U . . .
C26 C 0.7712(2) 0.39570(18) 0.83106(19) 0.0497(6) Uani 1 1 d . . . . .
H26 H 0.7223 0.3256 0.7828 0.060 Uiso 1 1 calc R U . . .
C27 C 0.8923(2) 0.45891(18) 0.79915(19) 0.0517(6) Uani 1 1 d . . . . .
C28 C 0.9746(2) 0.5651(2) 0.8608(2) 0.0683(7) Uani 1 1 d . . . . .
H28 H 0.9542 0.5995 0.9266 0.082 Uiso 1 1 calc R U . . .
C29 C 1.0866(3) 0.6202(2) 0.8255(3) 0.0838(9) Uani 1 1 d . . . . .
H29 H 1.1411 0.6914 0.8679 0.101 Uiso 1 1 calc R U . . .
C30 C 1.1184(3) 0.5713(3) 0.7291(3) 0.0922(10) Uani 1 1 d . . . . .
H30 H 1.1943 0.6092 0.7061 0.111 Uiso 1 1 calc R U . . .
C31 C 1.0388(3) 0.4669(3) 0.6668(3) 0.0930(9) Uani 1 1 d . . . . .
H31 H 1.0604 0.4331 0.6012 0.112 Uiso 1 1 calc R U . . .
C32 C 0.9258(2) 0.4113(2) 0.7013(2) 0.0712(7) Uani 1 1 d . . . . .
H32 H 0.8712 0.3406 0.6578 0.085 Uiso 1 1 calc R U . . .
C33 C 0.4477(2) 0.25201(19) 0.76146(18) 0.0495(6) Uani 1 1 d . . . . .
H33 H 0.4039 0.1807 0.7133 0.059 Uiso 1 1 calc R U . . .
C34 C 0.4386(2) 0.34497(19) 0.72281(18) 0.0506(6) Uani 1 1 d . . . . .
H34 H 0.4847 0.4158 0.7711 0.061 Uiso 1 1 calc R U . . .
C35 C 0.3653(2) 0.3492(2) 0.61409(19) 0.0533(6) Uani 1 1 d . . . . .
C36 C 0.3715(2) 0.4549(2) 0.5876(2) 0.0729(7) Uani 1 1 d . . . . .
H36 H 0.4219 0.5218 0.6400 0.087 Uiso 1 1 calc R U . . .
C37 C 0.3049(3) 0.4635(3) 0.4859(3) 0.0928(9) Uani 1 1 d . . . . .
H37 H 0.3109 0.5356 0.4701 0.111 Uiso 1 1 calc R U . . .
C38 C 0.2302(3) 0.3663(4) 0.4082(3) 0.0998(10) Uani 1 1 d . . . . .
H38 H 0.1848 0.3719 0.3395 0.120 Uiso 1 1 calc R U . . .
C39 C 0.2223(3) 0.2609(3) 0.4317(2) 0.1012(10) Uani 1 1 d . . . . .
H39 H 0.1722 0.1946 0.3784 0.121 Uiso 1 1 calc R U . . .
C40 C 0.2884(3) 0.2516(2) 0.5345(2) 0.0797(8) Uani 1 1 d . . . . .
H40 H 0.2810 0.1792 0.5499 0.096 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
C1 C8 1.338(3) . ?
C1 C2 1.459(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.340(3) . ?
C2 H2 0.9300 . ?
C3 C9 1.463(3) . ?
C3 C4 1.489(3) . ?
C4 C5 1.342(3) . ?
C4 C17 1.456(3) . ?
C5 C6 1.454(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.340(3) . ?
C6 H6 0.9300 . ?
C7 C33 1.459(3) . ?
C7 C8 1.499(3) . ?
C8 C25 1.464(3) . ?
C9 C10 1.326(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.468(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.326(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.472(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(3) . ?
C19 C24 1.383(3) . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.327(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.466(3) . ?
C26 H26 0.9300 . ?
C27 C32 1.382(3) . ?
C27 C28 1.383(3) . ?
C28 C29 1.378(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.364(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.363(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.384(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.333(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.458(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.383(3) . ?
C35 C40 1.384(3) . ?
C36 C37 1.376(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.364(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.363(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.388(3) . ?
C39 H39 0.9300 . ?
C40 H40 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
C8 C1 C2 124.8(2) . . ?
C8 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C1 125.14(19) . . ?
C3 C2 H2 117.4 . . ?
C1 C2 H2 117.4 . . ?
C2 C3 C9 120.97(19) . . ?
C2 C3 C4 120.39(18) . . ?
C9 C3 C4 118.48(17) . . ?
C5 C4 C17 118.17(19) . . ?
C5 C4 C3 121.04(18) . . ?
C17 C4 C3 120.77(18) . . ?
C4 C5 C6 125.79(19) . . ?
C4 C5 H5 117.1 . . ?
C6 C5 H5 117.1 . . ?
C7 C6 C5 125.2(2) . . ?
C7 C6 H6 117.4 . . ?
C5 C6 H6 117.4 . . ?
C6 C7 C33 119.77(19) . . ?
C6 C7 C8 120.30(18) . . ?
C33 C7 C8 119.92(17) . . ?
C1 C8 C25 120.1(2) . . ?
C1 C8 C7 121.84(18) . . ?
C25 C8 C7 118.05(18) . . ?
C10 C9 C3 124.81(19) . . ?
C10 C9 H9 117.6 . . ?
C3 C9 H9 117.6 . . ?
C9 C10 C11 128.5(2) . . ?
C9 C10 H10 115.7 . . ?
C11 C10 H10 115.7 . . ?
C12 C11 C16 117.4(2) . . ?
C12 C11 C10 123.9(2) . . ?
C16 C11 C10 118.7(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C18 C17 C4 130.1(2) . . ?
C18 C17 H17 115.0 . . ?
C4 C17 H17 115.0 . . ?
C17 C18 C19 123.0(2) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C24 117.5(2) . . ?
C20 C19 C18 120.7(2) . . ?
C24 C19 C18 121.8(2) . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 121.6(3) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
C26 C25 C8 126.0(2) . . ?
C26 C25 H25 117.0 . . ?
C8 C25 H25 117.0 . . ?
C25 C26 C27 127.2(2) . . ?
C25 C26 H26 116.4 . . ?
C27 C26 H26 116.4 . . ?
C32 C27 C28 117.7(2) . . ?
C32 C27 C26 118.6(2) . . ?
C28 C27 C26 123.6(2) . . ?
C29 C28 C27 120.6(3) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C27 C32 C31 121.3(3) . . ?
C27 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C34 C33 C7 126.3(2) . . ?
C34 C33 H33 116.9 . . ?
C7 C33 H33 116.9 . . ?
C33 C34 C35 127.9(2) . . ?
C33 C34 H34 116.0 . . ?
C35 C34 H34 116.0 . . ?
C36 C35 C40 117.5(2) . . ?
C36 C35 C34 119.5(2) . . ?
C40 C35 C34 123.0(2) . . ?
C37 C36 C35 121.7(3) . . ?
C37 C36 H36 119.1 . . ?
C35 C36 H36 119.1 . . ?
C38 C37 C36 120.0(3) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C39 C38 C37 119.7(3) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.7(3) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
C35 C40 C39 120.4(3) . . ?
C35 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?

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 C1 C2 C3 61.6(3) . . . . ?
C1 C2 C3 C9 -169.5(2) . . . . ?
C1 C2 C3 C4 5.7(3) . . . . ?
C2 C3 C4 C5 -68.7(3) . . . . ?
C9 C3 C4 C5 106.6(2) . . . . ?
C2 C3 C4 C17 112.9(2) . . . . ?
C9 C3 C4 C17 -71.8(3) . . . . ?
C17 C4 C5 C6 -179.07(17) . . . . ?
C3 C4 C5 C6 2.5(3) . . . . ?
C4 C5 C6 C7 60.4(3) . . . . ?
C5 C6 C7 C33 -174.84(18) . . . . ?
C5 C6 C7 C8 6.0(3) . . . . ?
C2 C1 C8 C25 -177.84(17) . . . . ?
C2 C1 C8 C7 1.5(3) . . . . ?
C6 C7 C8 C1 -67.9(3) . . . . ?
C33 C7 C8 C1 113.0(2) . . . . ?
C6 C7 C8 C25 111.4(2) . . . . ?
C33 C7 C8 C25 -67.7(2) . . . . ?
C2 C3 C9 C10 167.7(2) . . . . ?
C4 C3 C9 C10 -7.7(3) . . . . ?
C3 C9 C10 C11 -170.2(2) . . . . ?
C9 C10 C11 C12 -8.8(4) . . . . ?
C9 C10 C11 C16 170.1(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C11 0.7(4) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C10 C11 C16 C15 -179.9(2) . . . . ?
C5 C4 C17 C18 -175.3(2) . . . . ?
C3 C4 C17 C18 3.2(3) . . . . ?
C4 C17 C18 C19 178.39(19) . . . . ?
C17 C18 C19 C20 -152.2(2) . . . . ?
C17 C18 C19 C24 25.3(3) . . . . ?
C24 C19 C20 C21 -4.9(4) . . . . ?
C18 C19 C20 C21 172.6(2) . . . . ?
C19 C20 C21 C22 2.4(4) . . . . ?
C20 C21 C22 C23 1.0(5) . . . . ?
C21 C22 C23 C24 -1.8(5) . . . . ?
C22 C23 C24 C19 -0.8(5) . . . . ?
C20 C19 C24 C23 4.2(4) . . . . ?
C18 C19 C24 C23 -173.4(3) . . . . ?
C1 C8 C25 C26 177.85(19) . . . . ?
C7 C8 C25 C26 -1.5(3) . . . . ?
C8 C25 C26 C27 179.71(18) . . . . ?
C25 C26 C27 C32 179.9(2) . . . . ?
C25 C26 C27 C28 -1.1(3) . . . . ?
C32 C27 C28 C29 -0.6(3) . . . . ?
C26 C27 C28 C29 -179.6(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 0.0(5) . . . . ?
C29 C30 C31 C32 0.3(5) . . . . ?
C28 C27 C32 C31 1.0(4) . . . . ?
C26 C27 C32 C31 180.0(2) . . . . ?
C30 C31 C32 C27 -0.9(4) . . . . ?
C6 C7 C33 C34 176.2(2) . . . . ?
C8 C7 C33 C34 -4.7(3) . . . . ?
C7 C33 C34 C35 -178.51(19) . . . . ?
C33 C34 C35 C36 -177.9(2) . . . . ?
C33 C34 C35 C40 2.1(4) . . . . ?
C40 C35 C36 C37 -0.4(4) . . . . ?
C34 C35 C36 C37 179.5(2) . . . . ?
C35 C36 C37 C38 0.1(4) . . . . ?
C36 C37 C38 C39 -0.3(5) . . . . ?
C37 C38 C39 C40 0.7(5) . . . . ?
C36 C35 C40 C39 0.9(4) . . . . ?
C34 C35 C40 C39 -179.1(2) . . . . ?
C38 C39 C40 C35 -1.0(5) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2026057'
loop_
_audit_author_name
_audit_author_address
'Sudhadevi Antharjanam'
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-29 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br4'
_chemical_formula_sum            'C12 H12 Br4'
_chemical_formula_weight         475.86

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'

_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                   14.8169(9)
_cell_length_b                   23.1350(15)
_cell_length_c                   13.2408(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.823(3)
_cell_angle_gamma                90
_cell_volume                     4522.7(5)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    4613
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      19.70
_exptl_crystal_description       Block
_exptl_crystal_colour            brown

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    10.652
_shelx_estimated_absorpt_T_min   0.176
_shelx_estimated_absorpt_T_max   0.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3443
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker apex 2'
_diffrn_measurement_method       'ω and φ scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43078
_diffrn_reflns_av_unetI/netI     0.1802
_diffrn_reflns_av_R_equivalents  0.1794
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.379
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             7895
_reflns_number_gt                3286
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1037P)²+2.9041P] 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         7895
_refine_ls_number_parameters     433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2130
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.2393
_refine_ls_wR_factor_gt          0.1762
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C1 C 0.3560(9) 0.6599(6) 0.0451(11) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.3403(10) 0.6337(6) -0.0396(10) 0.044(4) Uani 1 1 d . . . . .
H2 H 0.377101 0.602120 -0.050589 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2715(10) 0.6477(5) -0.1203(11) 0.042(4) Uani 1 1 d . . . . .
H3 H 0.291656 0.657282 -0.182776 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1800(10) 0.6481(5) -0.1136(10) 0.038(4) Uani 1 1 d . . . . .
C5 C 0.1392(9) 0.6334(6) -0.0200(11) 0.039(4) Uani 1 1 d . . . . .
C6 C 0.1563(9) 0.6603(6) 0.0706(10) 0.040(4) Uani 1 1 d . . . . .
H6 H 0.127830 0.646242 0.125660 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2162(10) 0.7096(6) 0.0869(10) 0.044(4) Uani 1 1 d . . . . .
H7 H 0.190512 0.743709 0.107907 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3024(10) 0.7107(6) 0.0748(9) 0.039(4) Uani 1 1 d . U . . .
C9 C 0.3531(11) 0.7666(8) 0.0965(12) 0.077(6) Uani 1 1 d . U . . .
H9A H 0.402282 0.760104 0.148304 0.093 Uiso 1 1 calc R U . . .
H9B H 0.312522 0.795004 0.122038 0.093 Uiso 1 1 calc R U . . .
C10 C 0.4303(10) 0.6397(7) 0.1160(11) 0.062(5) Uani 1 1 d . . . . .
H10A H 0.467530 0.672348 0.139464 0.074 Uiso 1 1 calc R U . . .
H10B H 0.468007 0.613099 0.081620 0.074 Uiso 1 1 calc R U . . .
C11 C 0.0721(9) 0.5832(6) -0.0248(11) 0.051(4) Uani 1 1 d . . . . .
H11A H 0.023295 0.590925 -0.076514 0.062 Uiso 1 1 calc R U . . .
H11B H 0.046080 0.579699 0.039779 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1179(12) 0.6648(7) -0.1985(12) 0.079(6) Uani 1 1 d . . . . .
H12A H 0.066970 0.638310 -0.204540 0.095 Uiso 1 1 calc R U . . .
H12B H 0.148239 0.662681 -0.260490 0.095 Uiso 1 1 calc R U . . .
Br1 Br 0.13141(14) 0.51122(8) -0.05552(16) 0.0809(7) Uani 1 1 d . . . . .
Br2 Br 0.07364(12) 0.74427(8) -0.17996(13) 0.0699(6) Uani 1 1 d . . . . .
Br3 Br 0.40083(15) 0.79595(8) -0.0227(2) 0.1031(8) Uani 1 1 d . . . . .
Br4 Br 0.38312(15) 0.60098(11) 0.23214(14) 0.1011(9) Uani 1 1 d . . . . .
C13 C 0.2075(9) 0.5514(5) 0.4405(9) 0.028(3) Uani 1 1 d . . . . .
C14 C 0.2973(9) 0.5459(5) 0.4453(9) 0.032(3) Uani 1 1 d . . . . .
H14 H 0.329972 0.579758 0.437917 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3506(8) 0.4928(6) 0.4607(10) 0.033(3) Uani 1 1 d . . . . .
H15 H 0.381454 0.480088 0.406625 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3586(8) 0.4625(5) 0.5410(10) 0.030(3) Uani 1 1 d . . . . .
C17 C 0.3107(10) 0.4779(6) 0.6301(10) 0.040(4) Uani 1 1 d . . . . .
C18 C 0.2217(9) 0.4809(6) 0.6296(10) 0.038(4) Uani 1 1 d . . . . .
H18 H 0.198211 0.491933 0.689656 0.045 Uiso 1 1 calc R U . . .
C19 C 0.1559(8) 0.4683(5) 0.5421(9) 0.029(3) Uani 1 1 d . . . . .
H19 H 0.118510 0.436152 0.545346 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1479(8) 0.5012(5) 0.4581(9) 0.028(3) Uani 1 1 d . . . . .
C21 C 0.1662(10) 0.6077(6) 0.4178(10) 0.044(4) Uani 1 1 d . . . . .
H21A H 0.128938 0.605369 0.354113 0.053 Uiso 1 1 calc R U . . .
H21B H 0.213578 0.635846 0.409823 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0711(8) 0.4906(6) 0.3797(9) 0.034(3) Uani 1 1 d . . . . .
H22A H 0.028347 0.522301 0.381041 0.041 Uiso 1 1 calc R U . . .
H22B H 0.039926 0.455530 0.396956 0.041 Uiso 1 1 calc R U . . .
C23 C 0.4240(9) 0.4127(5) 0.5498(10) 0.043(4) Uani 1 1 d . . . . .
H23A H 0.473389 0.421759 0.600054 0.051 Uiso 1 1 calc R U . . .
H23B H 0.449188 0.406847 0.485336 0.051 Uiso 1 1 calc R U . . .
C24 C 0.3632(10) 0.4909(7) 0.7273(10) 0.054(4) Uani 1 1 d . . . . .
H24A H 0.403491 0.458964 0.746361 0.064 Uiso 1 1 calc R U . . .
H24B H 0.322467 0.496157 0.780170 0.064 Uiso 1 1 calc R U . . .
Br5 Br 0.10812(13) 0.48314(9) 0.24476(13) 0.0793(7) Uani 1 1 d . . . . .
Br6 Br 0.09213(12) 0.63378(7) 0.52325(13) 0.0615(5) Uani 1 1 d . . . . .
Br7 Br 0.43438(12) 0.56212(9) 0.71186(14) 0.0789(7) Uani 1 1 d . . . . .
Br8 Br 0.36447(14) 0.34165(8) 0.58891(17) 0.0874(7) Uani 1 1 d . . . . .
C25 C 0.1472(8) 0.2088(6) 0.4503(11) 0.035(3) Uani 1 1 d . . . . .
C26 C 0.1992(9) 0.1889(5) 0.3678(10) 0.032(3) Uani 1 1 d . . . . .
C27 C 0.2892(9) 0.1819(6) 0.3797(10) 0.039(4) Uani 1 1 d . . . . .
H27 H 0.315696 0.167664 0.323530 0.047 Uiso 1 1 calc R U . . .
C28 C 0.3522(8) 0.1937(5) 0.4695(10) 0.032(3) Uani 1 1 d . . . . .
H28 H 0.394600 0.222907 0.463785 0.038 Uiso 1 1 calc R U . . .
C29 C 0.3537(8) 0.1669(6) 0.5564(10) 0.031(3) Uani 1 1 d . . . . .
C30 C 0.2903(8) 0.1222(5) 0.5801(9) 0.027(3) Uani 1 1 d . . . . .
C31 C 0.2020(9) 0.1293(6) 0.5743(9) 0.043(4) Uani 1 1 d . . . . .
H31 H 0.167849 0.097601 0.591575 0.052 Uiso 1 1 calc R U . . .
C32 C 0.1504(9) 0.1831(7) 0.5428(11) 0.047(4) Uani 1 1 d . . . . .
H32 H 0.117464 0.200468 0.591234 0.057 Uiso 1 1 calc R U . . .
C33 C 0.0814(9) 0.2568(6) 0.4308(11) 0.055(5) Uani 1 1 d . . . . .
H33A H 0.056485 0.267168 0.493783 0.066 Uiso 1 1 calc R U . . .
H33B H 0.031903 0.243715 0.383814 0.066 Uiso 1 1 calc R U . . .
C34 C 0.1496(10) 0.1788(7) 0.2638(10) 0.059(5) Uani 1 1 d . . . . .
H34A H 0.192875 0.168724 0.215564 0.071 Uiso 1 1 calc R U . . .
H34B H 0.118770 0.213906 0.240528 0.071 Uiso 1 1 calc R U . . .
C35 C 0.3248(8) 0.0658(6) 0.6181(9) 0.037(4) Uani 1 1 d . . . . .
H35A H 0.274197 0.040556 0.629015 0.044 Uiso 1 1 calc R U . . .
H35B H 0.359986 0.071075 0.682582 0.044 Uiso 1 1 calc R U . . .
C36 C 0.4334(9) 0.1791(6) 0.6335(10) 0.046(4) Uani 1 1 d . . . . .
H36A H 0.467722 0.211588 0.610476 0.055 Uiso 1 1 calc R U . . .
H36B H 0.473099 0.145712 0.638535 0.055 Uiso 1 1 calc R U . . .
Br9 Br 0.39358(14) 0.19651(9) 0.76630(13) 0.0807(7) Uani 1 1 d . . . . .
Br10 Br 0.40054(11) 0.02982(7) 0.52124(14) 0.0631(6) Uani 1 1 d . . . . .
Br11 Br 0.06270(11) 0.11716(7) 0.27090(12) 0.0594(5) Uani 1 1 d . . . . .
Br12 Br 0.13616(14) 0.32497(8) 0.37510(18) 0.0880(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.279(17) . ?
C1 C10 1.462(17) . ?
C1 C8 1.489(19) . ?
C2 C3 1.450(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(19) . ?
C3 H3 0.9300 . ?
C4 C12 1.444(18) . ?
C4 C5 1.463(19) . ?
C5 C6 1.357(17) . ?
C5 C11 1.526(18) . ?
C6 C7 1.451(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.300(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.51(2) . ?
C9 Br3 1.907(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 Br4 1.960(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 Br1 1.942(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 Br2 1.974(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.333(16) . ?
C13 C21 1.460(17) . ?
C13 C20 1.488(17) . ?
C14 C15 1.465(17) . ?
C14 H14 0.9300 . ?
C15 C16 1.271(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.472(18) . ?
C16 C23 1.503(17) . ?
C17 C18 1.320(18) . ?
C17 C24 1.477(17) . ?
C18 C19 1.478(16) . ?
C18 H18 0.9300 . ?
C19 C20 1.346(16) . ?
C19 H19 0.9300 . ?
C20 C22 1.495(15) . ?
C21 Br6 1.943(13) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 Br5 1.920(12) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 Br8 1.955(13) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 Br7 1.976(15) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C32 1.358(18) . ?
C25 C26 1.463(18) . ?
C25 C33 1.486(17) . ?
C26 C27 1.340(17) . ?
C26 C34 1.523(18) . ?
C27 C28 1.474(17) . ?
C27 H27 0.9300 . ?
C28 C29 1.305(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.449(17) . ?
C29 C36 1.521(16) . ?
C30 C31 1.315(17) . ?
C30 C35 1.475(17) . ?
C31 C32 1.501(18) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 Br12 1.946(14) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 Br11 1.928(15) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 Br10 1.960(12) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 Br9 1.944(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 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 C1 C10 118.8(14) . . ?
C2 C1 C8 123.0(13) . . ?
C10 C1 C8 118.2(13) . . ?
C1 C2 C3 127.2(14) . . ?
C1 C2 H2 116.4 . . ?
C3 C2 H2 116.4 . . ?
C4 C3 C2 126.4(13) . . ?
C4 C3 H3 116.8 . . ?
C2 C3 H3 116.8 . . ?
C3 C4 C12 121.5(14) . . ?
C3 C4 C5 122.4(13) . . ?
C12 C4 C5 116.1(14) . . ?
C6 C5 C4 125.7(13) . . ?
C6 C5 C11 117.2(13) . . ?
C4 C5 C11 117.1(12) . . ?
C5 C6 C7 123.9(13) . . ?
C5 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C8 C7 C6 126.4(15) . . ?
C8 C7 H7 116.8 . . ?
C6 C7 H7 116.8 . . ?
C7 C8 C1 124.6(14) . . ?
C7 C8 C9 118.1(14) . . ?
C1 C8 C9 117.2(13) . . ?
C8 C9 Br3 111.1(10) . . ?
C8 C9 H9A 109.4 . . ?
Br3 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
Br3 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C1 C10 Br4 110.5(10) . . ?
C1 C10 H10A 109.5 . . ?
Br4 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
Br4 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C5 C11 Br1 110.9(9) . . ?
C5 C11 H11A 109.5 . . ?
Br1 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
Br1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C4 C12 Br2 110.4(10) . . ?
C4 C12 H12A 109.6 . . ?
Br2 C12 H12A 109.6 . . ?
C4 C12 H12B 109.6 . . ?
Br2 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C21 119.6(13) . . ?
C14 C13 C20 121.4(12) . . ?
C21 C13 C20 119.0(12) . . ?
C13 C14 C15 127.6(12) . . ?
C13 C14 H14 116.2 . . ?
C15 C14 H14 116.2 . . ?
C16 C15 C14 126.3(13) . . ?
C16 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
C15 C16 C17 121.2(12) . . ?
C15 C16 C23 120.2(12) . . ?
C17 C16 C23 118.4(11) . . ?
C18 C17 C16 123.9(12) . . ?
C18 C17 C24 116.6(14) . . ?
C16 C17 C24 119.5(13) . . ?
C17 C18 C19 125.9(13) . . ?
C17 C18 H18 117.1 . . ?
C19 C18 H18 117.1 . . ?
C20 C19 C18 122.8(12) . . ?
C20 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 C20 C13 124.0(11) . . ?
C19 C20 C22 119.4(12) . . ?
C13 C20 C22 116.5(11) . . ?
C13 C21 Br6 112.5(9) . . ?
C13 C21 H21A 109.1 . . ?
Br6 C21 H21A 109.1 . . ?
C13 C21 H21B 109.1 . . ?
Br6 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C20 C22 Br5 113.6(8) . . ?
C20 C22 H22A 108.8 . . ?
Br5 C22 H22A 108.8 . . ?
C20 C22 H22B 108.8 . . ?
Br5 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C16 C23 Br8 111.3(9) . . ?
C16 C23 H23A 109.4 . . ?
Br8 C23 H23A 109.4 . . ?
C16 C23 H23B 109.4 . . ?
Br8 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C17 C24 Br7 109.0(9) . . ?
C17 C24 H24A 109.9 . . ?
Br7 C24 H24A 109.9 . . ?
C17 C24 H24B 109.9 . . ?
Br7 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C32 C25 C26 123.7(13) . . ?
C32 C25 C33 117.2(13) . . ?
C26 C25 C33 119.0(12) . . ?
C27 C26 C25 122.1(13) . . ?
C27 C26 C34 119.2(13) . . ?
C25 C26 C34 118.7(12) . . ?
C26 C27 C28 129.0(13) . . ?
C26 C27 H27 115.5 . . ?
C28 C27 H27 115.5 . . ?
C29 C28 C27 125.9(13) . . ?
C29 C28 H28 117.1 . . ?
C27 C28 H28 117.1 . . ?
C28 C29 C30 124.5(12) . . ?
C28 C29 C36 117.3(12) . . ?
C30 C29 C36 117.9(11) . . ?
C31 C30 C29 123.9(12) . . ?
C31 C30 C35 116.4(12) . . ?
C29 C30 C35 119.6(11) . . ?
C30 C31 C32 126.9(14) . . ?
C30 C31 H31 116.5 . . ?
C32 C31 H31 116.5 . . ?
C25 C32 C31 126.3(13) . . ?
C25 C32 H32 116.8 . . ?
C31 C32 H32 116.8 . . ?
C25 C33 Br12 112.6(9) . . ?
C25 C33 H33A 109.1 . . ?
Br12 C33 H33A 109.1 . . ?
C25 C33 H33B 109.1 . . ?
Br12 C33 H33B 109.1 . . ?
H33A C33 H33B 107.8 . . ?
C26 C34 Br11 110.0(9) . . ?
C26 C34 H34A 109.7 . . ?
Br11 C34 H34A 109.7 . . ?
C26 C34 H34B 109.7 . . ?
Br11 C34 H34B 109.7 . . ?
H34A C34 H34B 108.2 . . ?
C30 C35 Br10 110.7(9) . . ?
C30 C35 H35A 109.5 . . ?
Br10 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
Br10 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C29 C36 Br9 111.6(9) . . ?
C29 C36 H36A 109.3 . . ?
Br9 C36 H36A 109.3 . . ?
C29 C36 H36B 109.3 . . ?
Br9 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?

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 C1 C2 C3 -178.6(13) . . . . ?
C8 C1 C2 C3 1(2) . . . . ?
C1 C2 C3 C4 -61(2) . . . . ?
C2 C3 C4 C12 177.7(13) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 58(2) . . . . ?
C12 C4 C5 C6 -120.3(15) . . . . ?
C3 C4 C5 C11 -121.6(14) . . . . ?
C12 C4 C5 C11 60.0(17) . . . . ?
C4 C5 C6 C7 2(2) . . . . ?
C11 C5 C6 C7 -178.2(13) . . . . ?
C5 C6 C7 C8 -62(2) . . . . ?
C6 C7 C8 C1 -2(2) . . . . ?
C6 C7 C8 C9 -179.6(13) . . . . ?
C2 C1 C8 C7 62(2) . . . . ?
C10 C1 C8 C7 -118.1(15) . . . . ?
C2 C1 C8 C9 -120.1(16) . . . . ?
C10 C1 C8 C9 59.3(17) . . . . ?
C7 C8 C9 Br3 -117.1(13) . . . . ?
C1 C8 C9 Br3 65.3(15) . . . . ?
C2 C1 C10 Br4 -107.8(14) . . . . ?
C8 C1 C10 Br4 72.7(15) . . . . ?
C6 C5 C11 Br1 -115.8(12) . . . . ?
C4 C5 C11 Br1 63.8(14) . . . . ?
C3 C4 C12 Br2 -102.6(15) . . . . ?
C5 C4 C12 Br2 75.7(14) . . . . ?
C21 C13 C14 C15 -176.0(12) . . . . ?
C20 C13 C14 C15 4(2) . . . . ?
C13 C14 C15 C16 -67(2) . . . . ?
C14 C15 C16 C17 2(2) . . . . ?
C14 C15 C16 C23 -173.1(12) . . . . ?
C15 C16 C17 C18 61(2) . . . . ?
C23 C16 C17 C18 -124.3(15) . . . . ?
C15 C16 C17 C24 -119.5(15) . . . . ?
C23 C16 C17 C24 55.4(18) . . . . ?
C16 C17 C18 C19 1(2) . . . . ?
C24 C17 C18 C19 -178.3(12) . . . . ?
C17 C18 C19 C20 -67(2) . . . . ?
C18 C19 C20 C13 4.1(19) . . . . ?
C18 C19 C20 C22 -171.1(11) . . . . ?
C14 C13 C20 C19 55.3(18) . . . . ?
C21 C13 C20 C19 -124.5(14) . . . . ?
C14 C13 C20 C22 -129.3(13) . . . . ?
C21 C13 C20 C22 50.9(15) . . . . ?
C14 C13 C21 Br6 -122.2(11) . . . . ?
C20 C13 C21 Br6 57.5(14) . . . . ?
C19 C20 C22 Br5 -129.7(11) . . . . ?
C13 C20 C22 Br5 54.7(13) . . . . ?
C15 C16 C23 Br8 -127.5(12) . . . . ?
C17 C16 C23 Br8 57.6(14) . . . . ?
C18 C17 C24 Br7 -114.6(13) . . . . ?
C16 C17 C24 Br7 65.7(14) . . . . ?
C32 C25 C26 C27 -54(2) . . . . ?
C33 C25 C26 C27 130.8(14) . . . . ?
C32 C25 C26 C34 129.0(14) . . . . ?
C33 C25 C26 C34 -46.0(18) . . . . ?
C25 C26 C27 C28 -2(2) . . . . ?
C34 C26 C27 C28 174.4(13) . . . . ?
C26 C27 C28 C29 65(2) . . . . ?
C27 C28 C29 C30 -3(2) . . . . ?
C27 C28 C29 C36 170.4(12) . . . . ?
C28 C29 C30 C31 -57(2) . . . . ?
C36 C29 C30 C31 129.7(14) . . . . ?
C28 C29 C30 C35 126.0(14) . . . . ?
C36 C29 C30 C35 -47.1(17) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C35 C30 C31 C32 177.1(12) . . . . ?
C26 C25 C32 C31 -4(2) . . . . ?
C33 C25 C32 C31 171.4(13) . . . . ?
C30 C31 C32 C25 63(2) . . . . ?
C32 C25 C33 Br12 130.8(12) . . . . ?
C26 C25 C33 Br12 -53.9(16) . . . . ?
C27 C26 C34 Br11 119.3(12) . . . . ?
C25 C26 C34 Br11 -63.8(14) . . . . ?
C31 C30 C35 Br10 124.9(11) . . . . ?
C29 C30 C35 Br10 -58.1(14) . . . . ?
C28 C29 C36 Br9 131.4(11) . . . . ?
C30 C29 C36 Br9 -55.0(14) . . . . ?

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
C10 H10B Br10 0.97 3.13 4.100(17) 176.6 2_655 yes
C12 H12B Br6 0.97 2.99 3.742(15) 135.3 1_554 yes
C22 H22B Br6 0.97 3.09 4.037(13) 165.1 3_566 yes
C23 H23A Br4 0.97 2.99 3.901(13) 157.0 3_666 yes
C33 H33B Br2 0.97 3.02 3.877(14) 148.5 3_565 yes
C34 H34B Br2 0.97 3.05 3.838(14) 138.9 3_565 yes
C34 H34B Br12 0.97 3.13 3.702(16) 119.6 . yes
C35 H35A Br5 0.97 3.06 3.912(13) 147.9 4_566 yes
C35 H35B Br9 0.97 3.13 3.701(13) 119.1 . yes
C36 H36A Br3 0.97 3.05 4.011(14) 169.0 2_645 yes
C36 H36B Br7 0.97 3.01 3.832(14) 142.8 2_646 yes

_refine_diff_density_max         1.784
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.177

# start Validation Reply Form
_vrf_PLAT341_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01892 Ang.  
RESPONSE: The crystal is weakly diffracting at higher Brag's angle. The weak
higher angle reflections also included in the refinement. This caused high
Rint and inaccuracies in the C-C bonds.
;
# end Validation Reply Form


####################################################################### 
# 
# 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_PHO
_database_code_depnum_ccdc_archive 'CCDC 2023451'
loop_
_audit_author_name
_audit_author_address
Sudhadevi
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H36 O12 P4, H2 O'

_chemical_formula_sum            'C20 H38 O13 P4'
_chemical_formula_weight         610.38

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.6392(6)
_cell_length_b                   18.8539(9)
_cell_length_c                   12.4008(7)
_cell_angle_alpha                90
_cell_angle_beta                 127.7290(10)
_cell_angle_gamma                90
_cell_volume                     2892.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8457
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.82

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26490
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.160
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2557
_reflns_number_gt                1937
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.0455P)²+5.3718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2557
_refine_ls_number_parameters     191
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
C1 C 0.8137(4) 0.5101(2) 0.5296(5) 0.0915(13) Uani 1 1 d . . . . .
H1A H 0.8198 0.5084 0.4572 0.137 Uiso 1 1 calc R U . . .
H1B H 0.8826 0.4995 0.6146 0.137 Uiso 1 1 calc R U . . .
H1C H 0.7614 0.4759 0.5128 0.137 Uiso 1 1 calc R U . . .
C3 C 0.6749(2) 0.67566(15) 0.5619(3) 0.0430(7) Uani 1 1 d . . . . .
H3A H 0.6519 0.6893 0.6160 0.052 Uiso 1 1 calc R U . . .
H3B H 0.7164 0.7148 0.5646 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5751(2) 0.66601(13) 0.4159(2) 0.0331(6) Uani 1 1 d . . . . .
C5 C 0.50541(19) 0.60361(13) 0.3852(2) 0.0313(5) Uani 1 1 d . . . . .
C6 C 0.4673(2) 0.59381(14) 0.4715(3) 0.0366(6) Uani 1 1 d . . . . .
H6A H 0.5295 0.5814 0.5632 0.044 Uiso 1 1 calc R U . . .
H6B H 0.4181 0.5538 0.4353 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3103(4) 0.6652(2) 0.6040(4) 0.0814(12) Uani 1 1 d . . . . .
H7A H 0.2846 0.6312 0.6358 0.122 Uiso 1 1 calc R U . . .
H7B H 0.3663 0.6935 0.6793 0.122 Uiso 1 1 calc R U . . .
H7C H 0.2517 0.6953 0.5369 0.122 Uiso 1 1 calc R U . . .
C8 C 0.2230(3) 0.6442(2) 0.2351(4) 0.0720(10) Uani 1 1 d . . . . .
H8A H 0.1716 0.6694 0.1519 0.108 Uiso 1 1 calc R U . . .
H8B H 0.2555 0.6071 0.2184 0.108 Uiso 1 1 calc R U . . .
H8C H 0.1868 0.6240 0.2684 0.108 Uiso 1 1 calc R U . . .
C9 C 0.4811(2) 0.55616(13) 0.2917(2) 0.0347(6) Uani 1 1 d . . . . .
H9 H 0.4357 0.5192 0.2773 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5485(2) 0.71407(13) 0.3213(3) 0.0362(6) Uani 1 1 d . . . . .
H10 H 0.5964 0.7515 0.3485 0.043 Uiso 1 1 calc R U . . .
O1 O 0.7809(2) 0.57798(15) 0.5360(3) 0.0849(9) Uani 1 1 d . . . . .
C2 C 0.9432(19) 0.6276(14) 0.8843(14) 0.076(5) Uani 0.49(2) 1 d D U P A 1
H2A H 1.0163 0.6408 0.9241 0.115 Uiso 0.49(2) 1 calc R U P A 1
H2B H 0.9110 0.6633 0.9043 0.115 Uiso 0.49(2) 1 calc R U P A 1
H2C H 0.9430 0.5830 0.9215 0.115 Uiso 0.49(2) 1 calc R U P A 1
O2 O 0.8848(5) 0.6214(6) 0.7450(6) 0.053(2) Uani 0.49(2) 1 d D U P A 1
C2' C 0.9381(15) 0.6142(14) 0.8931(13) 0.075(5) Uani 0.51(2) 1 d D U P A 2
H2'1 H 0.9881 0.6490 0.9584 0.113 Uiso 0.51(2) 1 calc R U P A 2
H2'2 H 0.9053 0.5897 0.9273 0.113 Uiso 0.51(2) 1 calc R U P A 2
H2'3 H 0.9760 0.5808 0.8778 0.113 Uiso 0.51(2) 1 calc R U P A 2
O2' O 0.8587(7) 0.6476(5) 0.7714(8) 0.065(3) Uani 0.51(2) 1 d D U P A 2
O3 O 0.72605(16) 0.54451(11) 0.6856(2) 0.0527(5) Uani 1 1 d . . . . .
O4 O 0.30536(17) 0.69239(11) 0.3350(2) 0.0558(6) Uani 1 1 d . . . . .
O5 O 0.47011(17) 0.72878(10) 0.5599(2) 0.0529(5) Uani 1 1 d . . . . .
O6 O 0.35195(19) 0.62938(12) 0.5455(2) 0.0618(6) Uani 1 1 d . . . . .
P2 P 0.40144(6) 0.66771(4) 0.48233(7) 0.0408(2) Uani 1 1 d . . . . .
P1 P 0.76237(6) 0.60082(4) 0.64137(8) 0.0494(2) Uani 1 1 d D . . . .
O7 O 0.5000 0.8336(2) 0.7500 0.0927(14) Uani 1 2 d S T P . .
H7 H 0.516(6) 0.808(3) 0.818(6) 0.17(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.399(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.513(4) . ?
C3 P1 1.784(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C10 1.332(3) . ?
C4 C5 1.486(3) . ?
C5 C9 1.323(3) . ?
C5 C6 1.521(3) . ?
C6 P2 1.786(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O6 1.409(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O4 1.437(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C9 1.474(5) 2_655 ?
C9 H9 0.9300 . ?
C10 C10 1.464(5) 2_655 ?
C10 H10 0.9300 . ?
O1 P1 1.562(3) . ?
C2 O2 1.379(13) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
O2 P1 1.568(5) . ?
C2' O2' 1.386(12) . ?
C2' H2'1 0.9600 . ?
C2' H2'2 0.9600 . ?
C2' H2'3 0.9600 . ?
O2' P1 1.635(7) . ?
O3 P1 1.460(2) . ?
O4 P2 1.566(2) . ?
O5 P2 1.463(2) . ?
O6 P2 1.574(2) . ?
O7 H7 0.86(5) . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 P1 116.54(19) . . ?
C4 C3 H3A 108.2 . . ?
P1 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
P1 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C10 C4 C5 121.9(2) . . ?
C10 C4 C3 120.7(2) . . ?
C5 C4 C3 117.4(2) . . ?
C9 C5 C4 122.2(2) . . ?
C9 C5 C6 120.5(2) . . ?
C4 C5 C6 117.2(2) . . ?
C5 C6 P2 116.77(18) . . ?
C5 C6 H6A 108.1 . . ?
P2 C6 H6A 108.1 . . ?
C5 C6 H6B 108.1 . . ?
P2 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 C9 126.3(2) . 2_655 ?
C5 C9 H9 116.8 . . ?
C9 C9 H9 116.8 2_655 . ?
C4 C10 C10 126.7(2) . 2_655 ?
C4 C10 H10 116.6 . . ?
C10 C10 H10 116.6 2_655 . ?
C1 O1 P1 124.2(2) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C2 O2 P1 126.0(13) . . ?
O2' C2' H2'1 109.5 . . ?
O2' C2' H2'2 109.5 . . ?
H2'1 C2' H2'2 109.5 . . ?
O2' C2' H2'3 109.5 . . ?
H2'1 C2' H2'3 109.5 . . ?
H2'2 C2' H2'3 109.5 . . ?
C2' O2' P1 120.0(13) . . ?
C8 O4 P2 122.1(2) . . ?
C7 O6 P2 124.0(2) . . ?
O5 P2 O4 109.11(12) . . ?
O5 P2 O6 114.91(12) . . ?
O4 P2 O6 107.69(13) . . ?
O5 P2 C6 115.98(13) . . ?
O4 P2 C6 109.27(12) . . ?
O6 P2 C6 99.28(12) . . ?
O3 P1 O1 115.30(15) . . ?
O3 P1 O2 115.7(2) . . ?
O1 P1 O2 89.7(5) . . ?
O3 P1 O2' 110.9(3) . . ?
O1 P1 O2' 116.3(6) . . ?
O3 P1 C3 116.07(13) . . ?
O1 P1 C3 103.17(13) . . ?
O2 P1 C3 113.3(5) . . ?
O2' P1 C3 92.9(4) . . ?

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
P1 C3 C4 C10 -132.2(2) . . . . ?
P1 C3 C4 C5 51.4(3) . . . . ?
C10 C4 C5 C9 59.9(4) . . . . ?
C3 C4 C5 C9 -123.8(3) . . . . ?
C10 C4 C5 C6 -123.4(3) . . . . ?
C3 C4 C5 C6 53.0(3) . . . . ?
C9 C5 C6 P2 -130.1(2) . . . . ?
C4 C5 C6 P2 53.1(3) . . . . ?
C4 C5 C9 C9 1.4(4) . . . 2_655 ?
C6 C5 C9 C9 -175.3(3) . . . 2_655 ?
C5 C4 C10 C10 0.1(4) . . . 2_655 ?
C3 C4 C10 C10 -176.1(3) . . . 2_655 ?
C8 O4 P2 O5 -179.1(2) . . . . ?
C8 O4 P2 O6 -53.7(3) . . . . ?
C8 O4 P2 C6 53.2(3) . . . . ?
C7 O6 P2 O5 41.1(3) . . . . ?
C7 O6 P2 O4 -80.7(3) . . . . ?
C7 O6 P2 C6 165.5(3) . . . . ?
C5 C6 P2 O5 -69.8(2) . . . . ?
C5 C6 P2 O4 54.0(2) . . . . ?
C5 C6 P2 O6 166.49(19) . . . . ?
C1 O1 P1 O3 -30.6(4) . . . . ?
C1 O1 P1 O2 87.9(5) . . . . ?
C1 O1 P1 O2' 101.7(5) . . . . ?
C1 O1 P1 C3 -158.2(3) . . . . ?
C2 O2 P1 O3 -41(2) . . . . ?
C2 O2 P1 O1 -158.9(18) . . . . ?
C2 O2 P1 C3 96.8(17) . . . . ?
C2' O2' P1 O3 39.8(18) . . . . ?
C2' O2' P1 O1 -94.6(16) . . . . ?
C2' O2' P1 C3 159.2(16) . . . . ?
C4 C3 P1 O3 -76.5(2) . . . . ?
C4 C3 P1 O1 50.6(2) . . . . ?
C4 C3 P1 O2 146.1(4) . . . . ?
C4 C3 P1 O2' 168.5(6) . . . . ?

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
C1 H1C O6 0.96 2.46 3.397(5) 166.7 5_666
C3 H3A O5 0.97 2.59 3.341(4) 134.6 .
C6 H6A O3 0.97 2.55 3.337(3) 137.8 .
C6 H6B O3 0.97 2.57 3.540(3) 173.6 5_666
O7 H7 O5 0.86(5) 2.05(5) 2.887(4) 165(6) 2_656

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2026058'
loop_
_audit_author_name
_audit_author_address
'sudhadevi Antharjanam'
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-29 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 O4'
_chemical_formula_sum            'C18 H24 O4'
_chemical_formula_weight         304.37

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'

_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                   6.9814(6)
_cell_length_b                   11.3970(10)
_cell_length_c                   11.8876(11)
_cell_angle_alpha                62.708(4)
_cell_angle_beta                 82.487(5)
_cell_angle_gamma                73.520(5)
_cell_volume                     806.04(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    1914
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      23.80
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11837
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11837
_reflns_number_gt                7615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
The crystal is found to be non-merohedrally twinned with 180 degrees 
rotation about (1 0 1) reciprocal lattice direction. 
The twin law (0.472 -0.522 0.573, 0 -1 0, 1.427 -0.522 -0.427)was
identified by TwinRotMat which is used for hklf5 generation. HKLF5
reflection format is used for refinement. The BASF factor is 0.118 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1346P)²+0.1698P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         11837
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.2275
_refine_ls_wR_factor_gt          0.1813
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.002
_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
C1 C 1.4013(6) 1.1064(5) 0.6219(4) 0.0527(12) Uani 1 1 d . . . . .
H1A H 1.439732 1.050351 0.709054 0.079 Uiso 1 1 calc R U . . .
H1B H 1.381224 1.200648 0.602219 0.079 Uiso 1 1 calc R U . . .
H1C H 1.504808 1.082506 0.568771 0.079 Uiso 1 1 calc R U . . .
C2 C 1.1516(7) 1.1599(4) 0.4608(4) 0.0490(12) Uani 1 1 d . . . . .
H2A H 1.256354 1.129850 0.411754 0.073 Uiso 1 1 calc R U . . .
H2B H 1.130764 1.256063 0.432800 0.073 Uiso 1 1 calc R U . . .
H2C H 1.030601 1.141885 0.450124 0.073 Uiso 1 1 calc R U . . .
C3 C 1.2101(5) 1.0837(4) 0.5994(4) 0.0354(10) Uani 1 1 d . . . . .
C4 C 1.2386(6) 0.8551(4) 0.7678(4) 0.0399(10) Uani 1 1 d . . . . .
H4A H 1.294533 0.892674 0.810609 0.048 Uiso 1 1 calc R U . . .
H4B H 1.326808 0.766667 0.782375 0.048 Uiso 1 1 calc R U . . .
C5 C 1.0349(6) 0.8378(4) 0.8221(3) 0.0338(10) Uani 1 1 d . . . . .
C6 C 0.9933(6) 0.7185(4) 0.8619(4) 0.0397(10) Uani 1 1 d . . . . .
H6 H 1.098773 0.648086 0.859852 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8033(6) 0.6833(4) 0.9086(4) 0.0425(11) Uani 1 1 d . . . . .
H7 H 0.751851 0.649033 0.864854 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6948(6) 0.6939(4) 1.0054(4) 0.0358(10) Uani 1 1 d . . . . .
C9 C 0.5115(6) 0.6386(4) 1.0466(4) 0.0403(10) Uani 1 1 d . . . . .
H9A H 0.400364 0.706490 1.057197 0.048 Uiso 1 1 calc R U . . .
H9B H 0.475822 0.619286 0.981739 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4915(6) 0.5317(4) 1.2762(4) 0.0393(10) Uani 1 1 d . . . . .
C11 C 0.5929(7) 0.3978(4) 1.3824(4) 0.0589(13) Uani 1 1 d . . . . .
H11A H 0.550111 0.325073 1.381820 0.088 Uiso 1 1 calc R U . . .
H11B H 0.557948 0.401096 1.461924 0.088 Uiso 1 1 calc R U . . .
H11C H 0.735047 0.381881 1.371054 0.088 Uiso 1 1 calc R U . . .
C12 C 0.2677(6) 0.5641(4) 1.2930(5) 0.0587(14) Uani 1 1 d . . . . .
H12A H 0.207670 0.649737 1.224339 0.088 Uiso 1 1 calc R U . . .
H12B H 0.234912 0.569842 1.371623 0.088 Uiso 1 1 calc R U . . .
H12C H 0.218191 0.493296 1.293772 0.088 Uiso 1 1 calc R U . . .
C13 C 0.7523(6) 0.6505(4) 1.2279(4) 0.0400(10) Uani 1 1 d . . . . .
H13A H 0.834487 0.559768 1.245040 0.048 Uiso 1 1 calc R U . . .
H13B H 0.808228 0.685122 1.273514 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7532(5) 0.7426(4) 1.0882(4) 0.0344(10) Uani 1 1 d . . . . .
C15 C 0.7905(6) 0.8645(4) 1.0462(4) 0.0416(11) Uani 1 1 d . . . . .
H15 H 0.824797 0.883917 1.107668 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7846(6) 0.9715(4) 0.9162(4) 0.0407(11) Uani 1 1 d . . . . .
H16 H 0.696691 1.055670 0.900818 0.049 Uiso 1 1 calc R U . . .
C17 C 0.8894(5) 0.9630(4) 0.8176(4) 0.0337(10) Uani 1 1 d . . . . .
C18 C 0.8790(5) 1.0896(4) 0.6944(4) 0.0370(10) Uani 1 1 d . . . . .
H18A H 0.858256 1.071850 0.625151 0.044 Uiso 1 1 calc R U . . .
H18B H 0.767672 1.162603 0.696138 0.044 Uiso 1 1 calc R U . . .
O1 O 1.2266(4) 0.9442(3) 0.6344(2) 0.0377(7) Uani 1 1 d . . . . .
O2 O 1.0631(4) 1.1300(3) 0.6755(2) 0.0378(7) Uani 1 1 d . . . . .
O3 O 0.5511(4) 0.6436(3) 1.2708(3) 0.0404(8) Uani 1 1 d . . . . .
O4 O 0.5491(4) 0.5153(3) 1.1643(2) 0.0393(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.508(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.516(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O1 1.420(4) . ?
C3 O2 1.427(4) . ?
C4 O1 1.437(4) . ?
C4 C5 1.510(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.325(5) . ?
C5 C17 1.480(5) . ?
C6 C7 1.461(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.327(5) . ?
C7 H7 0.9300 . ?
C8 C14 1.477(5) . ?
C8 C9 1.511(5) . ?
C9 O4 1.444(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O4 1.419(5) . ?
C10 O3 1.422(4) . ?
C10 C11 1.510(6) . ?
C10 C12 1.508(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O3 1.442(4) . ?
C13 C14 1.504(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.335(5) . ?
C15 C16 1.461(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.326(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.505(5) . ?
C18 O2 1.442(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 O2 110.3(3) . . ?
O1 C3 C1 112.2(3) . . ?
O2 C3 C1 105.5(3) . . ?
O1 C3 C2 105.6(3) . . ?
O2 C3 C2 111.5(3) . . ?
C1 C3 C2 111.9(3) . . ?
O1 C4 C5 111.0(3) . . ?
O1 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C17 124.6(4) . . ?
C6 C5 C4 119.8(4) . . ?
C17 C5 C4 115.5(3) . . ?
C5 C6 C7 128.4(4) . . ?
C5 C6 H6 115.8 . . ?
C7 C6 H6 115.8 . . ?
C8 C7 C6 128.2(4) . . ?
C8 C7 H7 115.9 . . ?
C6 C7 H7 115.9 . . ?
C7 C8 C14 124.1(4) . . ?
C7 C8 C9 119.9(3) . . ?
C14 C8 C9 115.6(3) . . ?
O4 C9 C8 110.4(3) . . ?
O4 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
O4 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O4 C10 O3 110.6(3) . . ?
O4 C10 C11 105.0(3) . . ?
O3 C10 C11 112.2(3) . . ?
O4 C10 C12 111.9(3) . . ?
O3 C10 C12 105.8(3) . . ?
C11 C10 C12 111.4(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 110.1(3) . . ?
O3 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O3 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C8 123.8(4) . . ?
C15 C14 C13 120.4(4) . . ?
C8 C14 C13 115.7(3) . . ?
C14 C15 C16 128.5(4) . . ?
C14 C15 H15 115.7 . . ?
C16 C15 H15 115.7 . . ?
C17 C16 C15 127.8(4) . . ?
C17 C16 H16 116.1 . . ?
C15 C16 H16 116.1 . . ?
C16 C17 C5 124.4(4) . . ?
C16 C17 C18 119.6(4) . . ?
C5 C17 C18 115.7(3) . . ?
O2 C18 C17 109.2(3) . . ?
O2 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O2 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C3 O1 C4 115.9(3) . . ?
C3 O2 C18 116.0(3) . . ?
C10 O3 C13 115.9(3) . . ?
C10 O4 C9 116.2(3) . . ?

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 C4 C5 C6 111.1(4) . . . . ?
O1 C4 C5 C17 -64.7(4) . . . . ?
C17 C5 C6 C7 0.1(7) . . . . ?
C4 C5 C6 C7 -175.2(4) . . . . ?
C5 C6 C7 C8 -57.9(7) . . . . ?
C6 C7 C8 C14 -1.5(7) . . . . ?
C6 C7 C8 C9 -173.9(4) . . . . ?
C7 C8 C9 O4 107.1(4) . . . . ?
C14 C8 C9 O4 -65.9(4) . . . . ?
C7 C8 C14 C15 57.8(6) . . . . ?
C9 C8 C14 C15 -129.5(4) . . . . ?
C7 C8 C14 C13 -127.3(4) . . . . ?
C9 C8 C14 C13 45.4(5) . . . . ?
O3 C13 C14 C15 108.8(4) . . . . ?
O3 C13 C14 C8 -66.3(4) . . . . ?
C8 C14 C15 C16 -0.6(7) . . . . ?
C13 C14 C15 C16 -175.3(4) . . . . ?
C14 C15 C16 C17 -58.9(6) . . . . ?
C15 C16 C17 C5 0.8(6) . . . . ?
C15 C16 C17 C18 -173.0(3) . . . . ?
C6 C5 C17 C16 55.6(6) . . . . ?
C4 C5 C17 C16 -128.8(4) . . . . ?
C6 C5 C17 C18 -130.4(4) . . . . ?
C4 C5 C17 C18 45.2(4) . . . . ?
C16 C17 C18 O2 106.7(4) . . . . ?
C5 C17 C18 O2 -67.6(4) . . . . ?
O2 C3 O1 C4 -46.5(4) . . . . ?
C1 C3 O1 C4 70.7(4) . . . . ?
C2 C3 O1 C4 -167.1(3) . . . . ?
C5 C4 O1 C3 94.5(4) . . . . ?
O1 C3 O2 C18 -44.4(4) . . . . ?
C1 C3 O2 C18 -165.7(3) . . . . ?
C2 C3 O2 C18 72.6(4) . . . . ?
C17 C18 O2 C3 95.6(4) . . . . ?
O4 C10 O3 C13 -45.7(4) . . . . ?
C11 C10 O3 C13 71.2(4) . . . . ?
C12 C10 O3 C13 -167.1(3) . . . . ?
C14 C13 O3 C10 95.1(4) . . . . ?
O3 C10 O4 C9 -44.6(4) . . . . ?
C11 C10 O4 C9 -165.9(3) . . . . ?
C12 C10 O4 C9 73.1(4) . . . . ?
C8 C9 O4 C10 94.2(4) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_31
_database_code_depnum_ccdc_archive 'CCDC 2026059'
loop_
_audit_author_name
_audit_author_address
'Sudhadevi Antharjanam'
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-29 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.6744(7)
_cell_length_b                   9.2737(6)
_cell_length_c                   11.2747(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.210(2)
_cell_angle_gamma                90
_cell_volume                     1113.29(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    969
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      23.3

_exptl_crystal_description       square
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4305
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.913
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             981
_reflns_number_gt                757
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0461P)²+1.1116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         981
_refine_ls_number_parameters     82
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.86228(19) 0.2053(2) 0.7097(2) 0.0328(5) Uani 1 1 d . . . . .
H1A H 0.9075 0.1299 0.7705 0.039 Uiso 1 1 calc R U . . .
H1B H 0.7820 0.2183 0.7148 0.039 Uiso 1 1 calc R U . . .
C2 C 0.93594(17) 0.3436(2) 0.74887(17) 0.0252(5) Uani 1 1 d . . . . .
C3 C 0.88654(18) 0.4522(2) 0.79019(19) 0.0288(5) Uani 1 1 d . . . . .
H3 H 0.8026 0.4411 0.7754 0.035 Uiso 1 1 calc R U . . .
C4 C 0.94541(18) 0.5862(2) 0.85532(19) 0.0274(5) Uani 1 1 d . . . . .
H4 H 0.9478 0.5987 0.9382 0.033 Uiso 1 1 calc R U . . .
C5 C 0.99599(17) 0.6928(2) 0.81388(18) 0.0253(5) Uani 1 1 d . . . . .
C6 C 1.03981(19) 0.8259(2) 0.8961(2) 0.0328(6) Uani 1 1 d . . . . .
H6A H 0.9866 0.9065 0.8515 0.039 Uiso 1 1 calc R U . . .
H6B H 1.0317 0.8114 0.9775 0.039 Uiso 1 1 calc R U . . .
O3 O 0.84108(14) 0.16085(17) 0.58133(14) 0.0423(5) Uani 1 1 d D . . . .
O4 O 1.16761(15) 0.86022(18) 0.92298(16) 0.0449(5) Uani 1 1 d D . . . .
H1O H 0.825(6) 0.0700(14) 0.571(6) 0.27(3) Uiso 1 1 d D . . . .
H2O H 1.226(4) 0.824(5) 0.991(3) 0.21(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.426(2) . ?
C1 C2 1.506(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.336(3) . ?
C2 C2 1.486(4) 2_756 ?
C3 C4 1.463(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.331(3) . ?
C4 H4 0.9300 . ?
C5 C5 1.481(4) 2_756 ?
C5 C6 1.502(3) . ?
C6 O4 1.431(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O3 H1O 0.860(2) . ?
O4 H2O 0.860(2) . ?

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
O3 C1 C2 112.62(16) . . ?
O3 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O3 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C2 124.73(14) . 2_756 ?
C3 C2 C1 117.92(18) . . ?
C2 C2 C1 117.05(12) 2_756 . ?
C2 C3 C4 129.35(18) . . ?
C2 C3 H3 115.3 . . ?
C4 C3 H3 115.3 . . ?
C5 C4 C3 129.74(18) . . ?
C5 C4 H4 115.1 . . ?
C3 C4 H4 115.1 . . ?
C4 C5 C5 123.74(14) . 2_756 ?
C4 C5 C6 118.79(17) . . ?
C5 C5 C6 117.33(13) 2_756 . ?
O4 C6 C5 112.00(16) . . ?
O4 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
O4 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C1 O3 H1O 111(4) . . ?
C6 O4 H2O 119(4) . . ?

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
O3 C1 C2 C3 125.36(19) . . . . ?
O3 C1 C2 C2 -60.6(3) . . . 2_756 ?
C2 C2 C3 C4 -5.8(3) 2_756 . . . ?
C1 C2 C3 C4 167.69(19) . . . . ?
C2 C3 C4 C5 61.4(3) . . . . ?
C3 C4 C5 C5 -1.3(4) . . . 2_756 ?
C3 C4 C5 C6 174.33(19) . . . . ?
C4 C5 C6 O4 126.62(19) . . . . ?
C5 C5 C6 O4 -57.5(3) 2_756 . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.043


# start Validation Reply Form
_vrf_PLAT417_31                  
;
PROBLEM: Short Inter D-H..H-D       H2O      ..H2O              1.47 Ang.  
RESPONSE: The positions of these H atoms were based on the most likely location 
for these atoms to be involved in O-H...O hydrogen bonding.
The H atom positions were idealized so that the O-H distances were 0.86\% 
and the O-H...O angle was close to 180\%; the exact O-H...O angles are 
probably less the 180\%. The idealized positions for the H atoms is 
reflected in the close intermolecular distances. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_323
_database_code_depnum_ccdc_archive 'CCDC 2023453'
loop_
_audit_author_name
_audit_author_address
Sudhadevi
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 N2'
_chemical_formula_weight         394.54

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8590(5)
_cell_length_b                   17.0662(11)
_cell_length_c                   19.6709(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2302.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1637
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      20.27

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9856
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.580
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4034
_reflns_number_gt                2584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0503P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 802 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration R
_refine_ls_number_reflns         4034
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
C1 C 0.3432(7) 0.8345(2) 0.32158(18) 0.0714(13) Uani 1 1 d . . . . .
H1 H 0.3791 0.8862 0.3131 0.086 Uiso 1 1 calc R U . . .
C2 C 0.2151(7) 0.7977(2) 0.27858(19) 0.0781(14) Uani 1 1 d . . . . .
H2 H 0.1669 0.8245 0.2410 0.094 Uiso 1 1 calc R U . . .
C3 C 0.1572(7) 0.7223(2) 0.29019(19) 0.0705(12) Uani 1 1 d . . . . .
H3 H 0.0684 0.6979 0.2615 0.085 Uiso 1 1 calc R U . . .
C4 C 0.2321(7) 0.6840(2) 0.3444(2) 0.0791(14) Uani 1 1 d . . . . .
H4 H 0.1953 0.6325 0.3529 0.095 Uiso 1 1 calc R U . . .
C5 C 0.3623(7) 0.7205(2) 0.38720(17) 0.0681(12) Uani 1 1 d . . . . .
H5 H 0.4126 0.6929 0.4240 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4194(6) 0.7962(2) 0.37701(16) 0.0525(10) Uani 1 1 d . . . . .
C7 C 0.5653(6) 0.8356(2) 0.42345(18) 0.0624(11) Uani 1 1 d . . . . .
H7 H 0.5911 0.8004 0.4617 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2990(6) 0.8997(2) 0.48533(16) 0.0585(10) Uani 1 1 d . . . . .
H8A H 0.2857 0.8475 0.5042 0.070 Uiso 1 1 calc R U . . .
H8B H 0.1919 0.9092 0.4542 0.070 Uiso 1 1 calc R U . . .
C9 C 0.3024(6) 0.96007(18) 0.54058(16) 0.0479(9) Uani 1 1 d . . . . .
C10 C 0.1220(6) 0.98473(19) 0.57421(18) 0.0553(10) Uani 1 1 d . . . . .
H10 H 0.0194 0.9985 0.5457 0.066 Uiso 1 1 calc R U . . .
C11 C 0.0877(6) 0.98974(19) 0.64039(17) 0.0536(10) Uani 1 1 d . . . . .
H11 H -0.0361 1.0061 0.6534 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2262(5) 0.97190(19) 0.69515(15) 0.0463(9) Uani 1 1 d . . . . .
C13 C 0.1614(6) 0.9257(2) 0.75663(15) 0.0545(10) Uani 1 1 d . . . . .
H13A H 0.0723 0.9560 0.7845 0.065 Uiso 1 1 calc R U . . .
H13B H 0.0983 0.8772 0.7433 0.065 Uiso 1 1 calc R U . . .
C14 C 0.4821(6) 0.9716(2) 0.77237(15) 0.0546(10) Uani 1 1 d . . . . .
H14A H 0.6135 0.9509 0.7690 0.066 Uiso 1 1 calc R U . . .
H14B H 0.4814 1.0147 0.8045 0.066 Uiso 1 1 calc R U . . .
C15 C 0.4085(6) 0.99735(18) 0.70422(15) 0.0470(9) Uani 1 1 d . . . . .
C16 C 0.5241(5) 1.05068(19) 0.66233(17) 0.0516(9) Uani 1 1 d . . . . .
H16 H 0.5830 1.0922 0.6850 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5554(5) 1.0470(2) 0.59551(16) 0.0526(10) Uani 1 1 d . . . . .
H17 H 0.6314 1.0866 0.5766 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4821(6) 0.98698(19) 0.54879(16) 0.0475(9) Uani 1 1 d . . . . .
C19 C 0.6169(6) 0.9487(2) 0.49872(16) 0.0554(10) Uani 1 1 d . . . . .
H19A H 0.6960 0.9876 0.4756 0.066 Uiso 1 1 calc R U . . .
H19B H 0.7022 0.9116 0.5213 0.066 Uiso 1 1 calc R U . . .
C20 C 0.3222(6) 0.8999(2) 0.86619(15) 0.0571(10) Uani 1 1 d . . . . .
H20 H 0.2684 0.9483 0.8854 0.069 Uiso 1 1 calc R U . . .
C21 C 0.1846(6) 0.83352(19) 0.88218(15) 0.0497(9) Uani 1 1 d . . . . .
C22 C 0.1816(7) 0.7652(2) 0.84507(17) 0.0624(11) Uani 1 1 d . . . . .
H22 H 0.2639 0.7600 0.8078 0.075 Uiso 1 1 calc R U . . .
C23 C 0.0593(7) 0.7044(2) 0.86207(18) 0.0658(12) Uani 1 1 d . . . . .
H23 H 0.0590 0.6590 0.8359 0.079 Uiso 1 1 calc R U . . .
C24 C -0.0618(7) 0.7099(2) 0.91707(18) 0.0678(12) Uani 1 1 d . . . . .
H24 H -0.1440 0.6687 0.9285 0.081 Uiso 1 1 calc R U . . .
C25 C -0.0599(7) 0.7774(3) 0.95507(18) 0.0725(13) Uani 1 1 d . . . . .
H25 H -0.1408 0.7819 0.9928 0.087 Uiso 1 1 calc R U . . .
C26 C 0.0614(6) 0.8384(2) 0.93747(16) 0.0602(11) Uani 1 1 d . . . . .
H26 H 0.0603 0.8839 0.9634 0.072 Uiso 1 1 calc R U . . .
C27 C 0.7579(7) 0.8504(3) 0.3865(2) 0.1098(18) Uani 1 1 d . . . . .
H27A H 0.7371 0.8869 0.3501 0.165 Uiso 1 1 calc R U . . .
H27B H 0.8063 0.8020 0.3683 0.165 Uiso 1 1 calc R U . . .
H27C H 0.8513 0.8717 0.4178 0.165 Uiso 1 1 calc R U . . .
C28 C 0.5205(7) 0.8847(3) 0.89873(17) 0.0862(15) Uani 1 1 d . . . . .
H28A H 0.5779 0.8388 0.8789 0.129 Uiso 1 1 calc R U . . .
H28B H 0.5043 0.8769 0.9467 0.129 Uiso 1 1 calc R U . . .
H28C H 0.6041 0.9290 0.8911 0.129 Uiso 1 1 calc R U . . .
N1 N 0.4874(4) 0.90856(16) 0.45059(13) 0.0528(8) Uani 1 1 d . . . . .
N2 N 0.3443(5) 0.91037(15) 0.79283(12) 0.0497(8) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.372(5) . ?
C1 C6 1.375(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(5) . ?
C7 N1 1.456(4) . ?
C7 C27 1.529(6) . ?
C7 H7 0.9800 . ?
C8 N1 1.469(4) . ?
C8 C9 1.498(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.325(5) . ?
C9 C10 1.465(5) . ?
C10 C11 1.326(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.468(5) . ?
C11 H11 0.9300 . ?
C12 C15 1.336(5) . ?
C12 C13 1.510(4) . ?
C13 N2 1.466(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.465(4) . ?
C14 C15 1.498(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.461(5) . ?
C16 C17 1.333(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.465(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.500(5) . ?
C19 N1 1.468(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N2 1.462(4) . ?
C20 C21 1.508(5) . ?
C20 C28 1.525(6) . ?
C20 H20 0.9800 . ?
C21 C22 1.376(4) . ?
C21 C26 1.380(5) . ?
C22 C23 1.375(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C2 C1 C6 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 117.2(4) . . ?
C5 C6 C7 121.5(3) . . ?
C1 C6 C7 121.3(3) . . ?
N1 C7 C6 111.0(3) . . ?
N1 C7 C27 110.5(3) . . ?
C6 C7 C27 111.0(3) . . ?
N1 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
C27 C7 H7 108.1 . . ?
N1 C8 C9 104.7(3) . . ?
N1 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
N1 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C18 C9 C10 129.1(3) . . ?
C18 C9 C8 110.0(3) . . ?
C10 C9 C8 120.8(3) . . ?
C11 C10 C9 127.7(3) . . ?
C11 C10 H10 116.1 . . ?
C9 C10 H10 116.1 . . ?
C10 C11 C12 126.3(4) . . ?
C10 C11 H11 116.8 . . ?
C12 C11 H11 116.8 . . ?
C15 C12 C11 129.5(3) . . ?
C15 C12 C13 109.8(3) . . ?
C11 C12 C13 120.3(3) . . ?
N2 C13 C12 103.3(3) . . ?
N2 C13 H13A 111.1 . . ?
C12 C13 H13A 111.1 . . ?
N2 C13 H13B 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
N2 C14 C15 103.7(3) . . ?
N2 C14 H14A 111.0 . . ?
C15 C14 H14A 111.0 . . ?
N2 C14 H14B 111.0 . . ?
C15 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
C12 C15 C16 129.4(3) . . ?
C12 C15 C14 109.9(3) . . ?
C16 C15 C14 120.3(3) . . ?
C17 C16 C15 127.9(3) . . ?
C17 C16 H16 116.1 . . ?
C15 C16 H16 116.1 . . ?
C16 C17 C18 126.6(3) . . ?
C16 C17 H17 116.7 . . ?
C18 C17 H17 116.7 . . ?
C9 C18 C17 129.6(3) . . ?
C9 C18 C19 110.0(3) . . ?
C17 C18 C19 120.3(3) . . ?
N1 C19 C18 104.7(3) . . ?
N1 C19 H19A 110.8 . . ?
C18 C19 H19A 110.8 . . ?
N1 C19 H19B 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
N2 C20 C21 111.2(3) . . ?
N2 C20 C28 110.1(3) . . ?
C21 C20 C28 110.1(3) . . ?
N2 C20 H20 108.5 . . ?
C21 C20 H20 108.5 . . ?
C28 C20 H20 108.5 . . ?
C22 C21 C26 117.4(4) . . ?
C22 C21 C20 122.4(3) . . ?
C26 C21 C20 120.2(3) . . ?
C21 C22 C23 121.3(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 118.9(4) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C26 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 121.5(4) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C7 C27 H27A 109.5 . . ?
C7 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C7 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C28 H28A 109.5 . . ?
C20 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C20 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C7 N1 C19 114.4(3) . . ?
C7 N1 C8 113.9(3) . . ?
C19 N1 C8 106.3(3) . . ?
C20 N2 C14 115.1(3) . . ?
C20 N2 C13 114.4(3) . . ?
C14 N2 C13 106.9(2) . . ?

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
C6 C1 C2 C3 1.0(7) . . . . ?
C1 C2 C3 C4 -1.3(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C4 C5 C6 C7 -178.9(4) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C1 C6 C7 178.2(4) . . . . ?
C5 C6 C7 N1 -125.5(4) . . . . ?
C1 C6 C7 N1 56.4(5) . . . . ?
C5 C6 C7 C27 111.1(5) . . . . ?
C1 C6 C7 C27 -66.9(5) . . . . ?
N1 C8 C9 C18 -13.8(4) . . . . ?
N1 C8 C9 C10 162.8(3) . . . . ?
C18 C9 C10 C11 -53.7(6) . . . . ?
C8 C9 C10 C11 130.5(4) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C15 51.0(6) . . . . ?
C10 C11 C12 C13 -136.7(4) . . . . ?
C15 C12 C13 N2 -14.7(4) . . . . ?
C11 C12 C13 N2 171.6(3) . . . . ?
C11 C12 C15 C16 0.1(6) . . . . ?
C13 C12 C15 C16 -172.8(3) . . . . ?
C11 C12 C15 C14 172.4(3) . . . . ?
C13 C12 C15 C14 -0.5(4) . . . . ?
N2 C14 C15 C12 15.7(4) . . . . ?
N2 C14 C15 C16 -171.3(3) . . . . ?
C12 C15 C16 C17 -50.7(6) . . . . ?
C14 C15 C16 C17 137.7(4) . . . . ?
C15 C16 C17 C18 -1.1(6) . . . . ?
C10 C9 C18 C17 2.6(6) . . . . ?
C8 C9 C18 C17 178.8(3) . . . . ?
C10 C9 C18 C19 -174.9(3) . . . . ?
C8 C9 C18 C19 1.3(4) . . . . ?
C16 C17 C18 C9 50.5(6) . . . . ?
C16 C17 C18 C19 -132.3(4) . . . . ?
C9 C18 C19 N1 11.7(4) . . . . ?
C17 C18 C19 N1 -166.1(3) . . . . ?
N2 C20 C21 C22 38.9(5) . . . . ?
C28 C20 C21 C22 -83.4(4) . . . . ?
N2 C20 C21 C26 -144.0(3) . . . . ?
C28 C20 C21 C26 93.7(4) . . . . ?
C26 C21 C22 C23 0.6(6) . . . . ?
C20 C21 C22 C23 177.7(4) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C22 C23 C24 C25 0.2(6) . . . . ?
C23 C24 C25 C26 0.4(6) . . . . ?
C24 C25 C26 C21 -0.6(6) . . . . ?
C22 C21 C26 C25 0.1(6) . . . . ?
C20 C21 C26 C25 -177.2(4) . . . . ?
C6 C7 N1 C19 177.4(3) . . . . ?
C27 C7 N1 C19 -59.1(4) . . . . ?
C6 C7 N1 C8 54.8(4) . . . . ?
C27 C7 N1 C8 178.4(3) . . . . ?
C18 C19 N1 C7 -146.4(3) . . . . ?
C18 C19 N1 C8 -19.8(3) . . . . ?
C9 C8 N1 C7 147.5(3) . . . . ?
C9 C8 N1 C19 20.6(3) . . . . ?
C21 C20 N2 C14 -177.5(3) . . . . ?
C28 C20 N2 C14 -55.2(4) . . . . ?
C21 C20 N2 C13 58.0(4) . . . . ?
C28 C20 N2 C13 -179.7(3) . . . . ?
C15 C14 N2 C20 -153.0(3) . . . . ?
C15 C14 N2 C13 -24.7(3) . . . . ?
C12 C13 N2 C20 153.0(3) . . . . ?
C12 C13 N2 C14 24.3(3) . . . . ?

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_COT
_database_code_depnum_ccdc_archive 'CCDC 2023452'
loop_
_audit_author_name
_audit_author_address
Sudhadevi
;SAIF, IIT MADRAS
India
;
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H36 N12'
_chemical_formula_sum            'C44 H36 N12'
_chemical_formula_weight         732.85

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.8429(11)
_cell_length_b                   14.4588(7)
_cell_length_c                   12.0020(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.4550(10)
_cell_angle_gamma                90
_cell_volume                     3704.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36006
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.191
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3632
_reflns_number_gt                2505
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0543P)²+2.8486P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0114(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3632
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C1 C 0.61678(10) 0.29550(16) 0.20347(18) 0.0599(6) Uani 1 1 d . . . . .
H1A H 0.6137 0.3592 0.1762 0.072 Uiso 1 1 calc R U . . .
H1B H 0.6586 0.2860 0.2701 0.072 Uiso 1 1 calc R U . . .
C2 C 0.56932(9) 0.27850(14) 0.25214(17) 0.0518(5) Uani 1 1 d . . . . .
C3 C 0.57683(10) 0.19354(15) 0.32765(18) 0.0553(5) Uani 1 1 d . . . . .
C4 C 0.63995(11) 0.17608(19) 0.4365(2) 0.0715(7) Uani 1 1 d . . . . .
H4A H 0.6410 0.1137 0.4672 0.086 Uiso 1 1 calc R U . . .
H4B H 0.6724 0.1810 0.4089 0.086 Uiso 1 1 calc R U . . .
C5 C 0.53154(10) 0.13206(16) 0.30266(19) 0.0621(6) Uani 1 1 d . . . . .
H5 H 0.5407 0.0831 0.3583 0.074 Uiso 1 1 calc R U . . .
C6 C 0.52444(9) 0.34077(15) 0.22878(17) 0.0538(5) Uani 1 1 d . . . . .
H6 H 0.5240 0.3906 0.1793 0.065 Uiso 1 1 calc R U . . .
C7 C 0.64899(9) 0.20362(15) 0.06272(17) 0.0544(5) Uani 1 1 d . . . . .
H7 H 0.6922 0.2114 0.1037 0.065 Uiso 1 1 calc R U . . .
C8 C 0.61552(9) 0.15904(14) -0.04692(17) 0.0502(5) Uani 1 1 d . . . . .
C9 C 0.63555(9) 0.11349(14) -0.13258(17) 0.0520(5) Uani 1 1 d . . . . .
C10 C 0.69820(11) 0.1084(2) -0.1062(2) 0.0872(9) Uani 1 1 d . . . . .
H10 H 0.7283 0.1347 -0.0334 0.105 Uiso 1 1 calc R U . . .
C11 C 0.71653(13) 0.0647(3) -0.1870(3) 0.1050(11) Uani 1 1 d . . . . .
H11 H 0.7588 0.0623 -0.1685 0.126 Uiso 1 1 calc R U . . .
C12 C 0.67289(13) 0.0248(2) -0.2944(2) 0.0834(8) Uani 1 1 d . . . . .
H12 H 0.6855 -0.0063 -0.3473 0.100 Uiso 1 1 calc R U . . .
C13 C 0.61109(12) 0.03110(17) -0.3230(2) 0.0708(6) Uani 1 1 d . . . . .
H13 H 0.5813 0.0052 -0.3965 0.085 Uiso 1 1 calc R U . . .
C14 C 0.59210(10) 0.07586(15) -0.24358(19) 0.0599(5) Uani 1 1 d . . . . .
H14 H 0.5496 0.0807 -0.2651 0.072 Uiso 1 1 calc R U . . .
C15 C 0.61467(9) 0.27201(14) 0.58458(18) 0.0540(5) Uani 1 1 d . . . . .
H15 H 0.5726 0.2575 0.5571 0.065 Uiso 1 1 calc R U . . .
C16 C 0.65063(9) 0.32847(15) 0.68154(18) 0.0553(5) Uani 1 1 d . . . . .
C17 C 0.63527(10) 0.38228(15) 0.76769(18) 0.0596(6) Uani 1 1 d . . . . .
C18 C 0.58678(11) 0.35771(16) 0.7947(2) 0.0656(6) Uani 1 1 d . . . . .
H18 H 0.5622 0.3066 0.7557 0.079 Uiso 1 1 calc R U . . .
C19 C 0.57422(14) 0.40835(19) 0.8796(2) 0.0830(8) Uani 1 1 d . . . . .
H19 H 0.5413 0.3909 0.8968 0.100 Uiso 1 1 calc R U . . .
C20 C 0.60978(17) 0.4834(2) 0.9378(2) 0.0969(10) Uani 1 1 d . . . . .
H20 H 0.6015 0.5167 0.9951 0.116 Uiso 1 1 calc R U . . .
C21 C 0.65765(17) 0.5097(2) 0.9116(3) 0.1022(11) Uani 1 1 d . . . . .
H21 H 0.6818 0.5611 0.9511 0.123 Uiso 1 1 calc R U . . .
C22 C 0.67057(13) 0.46060(18) 0.8271(2) 0.0846(8) Uani 1 1 d . . . . .
H22 H 0.7030 0.4797 0.8094 0.101 Uiso 1 1 calc R U . . .
N1 N 0.55426(8) 0.16376(15) -0.07170(16) 0.0709(6) Uani 1 1 d . . . . .
N2 N 0.54878(8) 0.21046(16) 0.01661(16) 0.0730(6) Uani 1 1 d . . . . .
N3 N 0.60709(7) 0.23386(12) 0.09944(14) 0.0537(4) Uani 1 1 d . . . . .
N4 N 0.65279(8) 0.24193(13) 0.53751(15) 0.0599(5) Uani 1 1 d . . . . .
N5 N 0.71077(8) 0.27657(18) 0.6022(2) 0.0814(7) Uani 1 1 d . . . . .
N6 N 0.70932(9) 0.32974(17) 0.68970(19) 0.0787(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.466(3) . ?
C1 C2 1.507(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C6 1.329(3) . ?
C2 C3 1.489(3) . ?
C3 C5 1.326(3) . ?
C3 C4 1.511(3) . ?
C4 N4 1.462(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C5 1.472(4) 2_655 ?
C5 H5 0.9300 . ?
C6 C6 1.465(4) 2_655 ?
C6 H6 0.9300 . ?
C7 N3 1.332(2) . ?
C7 C8 1.360(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.356(2) . ?
C8 C9 1.468(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N4 1.339(3) . ?
C15 C16 1.366(3) . ?
C15 H15 0.9300 . ?
C16 N6 1.359(3) . ?
C16 C17 1.465(3) . ?
C17 C18 1.379(3) . ?
C17 C22 1.402(3) . ?
C18 C19 1.391(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 N2 1.311(2) . ?
N2 N3 1.343(2) . ?
N4 N5 1.345(3) . ?
N5 N6 1.315(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 111.73(16) . . ?
N3 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N3 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C6 C2 C3 123.66(18) . . ?
C6 C2 C1 118.73(19) . . ?
C3 C2 C1 117.58(18) . . ?
C5 C3 C2 123.39(19) . . ?
C5 C3 C4 118.7(2) . . ?
C2 C3 C4 117.9(2) . . ?
N4 C4 C3 111.59(17) . . ?
N4 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N4 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C3 C5 C5 127.74(16) . 2_655 ?
C3 C5 H5 116.1 . . ?
C5 C5 H5 116.1 2_655 . ?
C2 C6 C6 128.09(15) . 2_655 ?
C2 C6 H6 116.0 . . ?
C6 C6 H6 116.0 2_655 . ?
N3 C7 C8 105.82(17) . . ?
N3 C7 H7 127.1 . . ?
C8 C7 H7 127.1 . . ?
N1 C8 C7 107.38(17) . . ?
N1 C8 C9 121.56(18) . . ?
C7 C8 C9 131.04(18) . . ?
C14 C9 C10 117.9(2) . . ?
C14 C9 C8 120.86(18) . . ?
C10 C9 C8 121.23(19) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 120.8(2) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N4 C15 C16 105.50(18) . . ?
N4 C15 H15 127.3 . . ?
C16 C15 H15 127.3 . . ?
N6 C16 C15 107.7(2) . . ?
N6 C16 C17 121.0(2) . . ?
C15 C16 C17 131.24(19) . . ?
C18 C17 C22 117.7(2) . . ?
C18 C17 C16 121.91(19) . . ?
C22 C17 C16 120.4(2) . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
N2 N1 C8 109.51(17) . . ?
N1 N2 N3 106.56(16) . . ?
C7 N3 N2 110.72(16) . . ?
C7 N3 C1 128.63(17) . . ?
N2 N3 C1 120.12(17) . . ?
C15 N4 N5 110.62(19) . . ?
C15 N4 C4 129.09(18) . . ?
N5 N4 C4 120.17(19) . . ?
N6 N5 N4 107.02(18) . . ?
N5 N6 C16 109.11(19) . . ?

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
N3 C1 C2 C6 -107.7(2) . . . . ?
N3 C1 C2 C3 74.2(2) . . . . ?
C6 C2 C3 C5 55.2(3) . . . . ?
C1 C2 C3 C5 -126.8(2) . . . . ?
C6 C2 C3 C4 -126.2(2) . . . . ?
C1 C2 C3 C4 51.8(2) . . . . ?
C5 C3 C4 N4 -111.3(2) . . . . ?
C2 C3 C4 N4 70.1(2) . . . . ?
C2 C3 C5 C5 3.0(4) . . . 2_655 ?
C4 C3 C5 C5 -175.6(2) . . . 2_655 ?
C3 C2 C6 C6 1.0(3) . . . 2_655 ?
C1 C2 C6 C6 -177.0(2) . . . 2_655 ?
N3 C7 C8 N1 -0.4(2) . . . . ?
N3 C7 C8 C9 178.3(2) . . . . ?
N1 C8 C9 C14 1.7(3) . . . . ?
C7 C8 C9 C14 -176.8(2) . . . . ?
N1 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C14 C9 C10 C11 -1.8(4) . . . . ?
C8 C9 C10 C11 179.4(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C11 C12 C13 2.1(5) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C10 C9 C14 C13 2.7(3) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
N4 C15 C16 N6 -0.4(2) . . . . ?
N4 C15 C16 C17 179.20(19) . . . . ?
N6 C16 C17 C18 -154.8(2) . . . . ?
C15 C16 C17 C18 25.6(3) . . . . ?
N6 C16 C17 C22 24.3(3) . . . . ?
C15 C16 C17 C22 -155.3(2) . . . . ?
C22 C17 C18 C19 -1.0(3) . . . . ?
C16 C17 C18 C19 178.1(2) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C17 -0.7(4) . . . . ?
C18 C17 C22 C21 1.4(3) . . . . ?
C16 C17 C22 C21 -177.8(2) . . . . ?
C7 C8 N1 N2 1.1(3) . . . . ?
C9 C8 N1 N2 -177.79(19) . . . . ?
C8 N1 N2 N3 -1.3(3) . . . . ?
C8 C7 N3 N2 -0.4(2) . . . . ?
C8 C7 N3 C1 -171.94(19) . . . . ?
N1 N2 N3 C7 1.1(3) . . . . ?
N1 N2 N3 C1 173.42(19) . . . . ?
C2 C1 N3 C7 -153.0(2) . . . . ?
C2 C1 N3 N2 36.2(3) . . . . ?
C16 C15 N4 N5 0.7(2) . . . . ?
C16 C15 N4 C4 176.65(19) . . . . ?
C3 C4 N4 C15 43.5(3) . . . . ?
C3 C4 N4 N5 -140.9(2) . . . . ?
C15 N4 N5 N6 -0.7(2) . . . . ?
C4 N4 N5 N6 -177.10(19) . . . . ?
N4 N5 N6 C16 0.5(3) . . . . ?
C15 C16 N6 N5 0.0(2) . . . . ?
C17 C16 N6 N5 -179.69(19) . . . . ?

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
C7 H7 N6 0.93 2.61 3.396(3) 142.1 7_656

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039

