# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_Biphen_2Cl
_database_code_depnum_ccdc_archive 'CCDC 2503994'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2025-11-19 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
Crystals diffracted well and refinement proceeded smoothly. NH and OH hydrogen
atoms were visible in the difference map and their positions were refined with
restraints. Otherwise it was not necessary to use any crystallographic 
restraints in the refinement.
;

_cell_length_a                   7.38710(10)
_cell_length_b                   17.4215(2)
_cell_length_c                   18.6866(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.1555(14)
_cell_angle_gamma                90
_cell_volume                     2367.18(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C22 H34 Cl2 N4 O'
_chemical_formula_moiety         'C22 H32 N4, 2(Cl), H2 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         441.44

_cell_measurement_reflns_used    10097
_cell_measurement_theta_min      4.80
_cell_measurement_theta_max      77.44
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_max          0.18

_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    2.615

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip, (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            26689
_diffrn_reflns_av_unetI/netI     3.410
_reflns_number_total             4286
_diffrn_reflns_av_R_equivalents  0.055

_diffrn_reflns_theta_min         3.494
_diffrn_reflns_theta_max         67.735
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        67.735
_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   1.52
_oxford_diffrn_Wilson_scale      2.47

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.31

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     20
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4285
_refine_ls_R_factor_ref          0.0456
_refine_ls_wR_factor_ref         0.0953
_refine_ls_goodness_of_fit_ref   1.0292
_refine_ls_shift/su_max          0.0008934
_refine_ls_shift/su_mean         0.0000356

# Computed with I/sigma = -10 
_reflns_number_all               4285
_refine_ls_R_factor_all          0.0456
_refine_ls_wR_factor_all         0.0953

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3766
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.0918


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.38P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C -0.5105(3) 0.13171(12) 0.72160(11) 0.0300 1.0000 Uani . . . . . .
C2 C -0.4841(3) 0.13946(10) 0.64348(11) 0.0237 1.0000 Uani D . . . . .
N3 N -0.3912(2) 0.07118(9) 0.62097(9) 0.0221 1.0000 Uani D . . . . .
C4 C -0.2394(4) -0.12218(13) 0.62952(14) 0.0460 1.0000 Uani . . . . . .
C5 C -0.2577(3) -0.06736(10) 0.56609(11) 0.0240 1.0000 Uani D . . . . .
N6 N -0.1551(2) 0.00398(8) 0.58498(9) 0.0212 1.0000 Uani D . . . . .
C7 C -0.2222(2) 0.06732(10) 0.60794(10) 0.0188 1.0000 Uani D . . . . .
C8 C -0.1013(2) 0.13646(10) 0.61433(10) 0.0191 1.0000 Uani . . . . . .
C9 C -0.0469(3) 0.17544(10) 0.67981(10) 0.0226 1.0000 Uani . . . . . .
C10 C 0.0619(3) 0.24057(10) 0.68105(10) 0.0223 1.0000 Uani . . . . . .
C11 C 0.1153(2) 0.26850(10) 0.61793(10) 0.0185 1.0000 Uani . . . . . .
C12 C 0.0591(2) 0.22861(10) 0.55294(10) 0.0195 1.0000 Uani . . . . . .
C13 C -0.0471(2) 0.16294(10) 0.55123(10) 0.0199 1.0000 Uani . . . . . .
C14 C 0.2278(2) 0.33947(10) 0.61879(10) 0.0183 1.0000 Uani . . . . . .
C15 C 0.1971(2) 0.39024(10) 0.56010(10) 0.0197 1.0000 Uani . . . . . .
C16 C 0.3002(2) 0.45673(10) 0.56064(10) 0.0198 1.0000 Uani . . . . . .
C17 C 0.4381(2) 0.47362(10) 0.61942(10) 0.0188 1.0000 Uani . . . . . .
C18 C 0.4700(2) 0.42334(10) 0.67890(10) 0.0207 1.0000 Uani . . . . . .
C19 C 0.3655(2) 0.35710(10) 0.67809(10) 0.0208 1.0000 Uani . . . . . .
C20 C 0.5499(2) 0.54426(10) 0.61673(9) 0.0181 1.0000 Uani D . . . . .
N21 N 0.7304(2) 0.54237(8) 0.63261(9) 0.0205 1.0000 Uani D . . . . .
C22 C 0.8496(3) 0.47427(10) 0.64184(11) 0.0243 1.0000 Uani D . . . . .
C23 C 0.9604(3) 0.46931(12) 0.71757(12) 0.0325 1.0000 Uani . . . . . .
N24 N 0.4587(2) 0.60782(8) 0.59523(9) 0.0212 1.0000 Uani D . . . . .
C25 C 0.5405(3) 0.68234(11) 0.58271(12) 0.0268 1.0000 Uani D . . . . .
C26 C 0.4335(3) 0.71915(13) 0.51561(13) 0.0375 1.0000 Uani . . . . . .
Cl1 Cl 0.94191(6) 0.15491(3) 0.87792(2) 0.0245 1.0000 Uani . . . . . .
Cl2 Cl 0.73051(6) 0.45941(3) 0.89533(3) 0.0274 1.0000 Uani . . . . . .
O101 O 0.6894(3) 0.29980(10) 0.80636(12) 0.0614 1.0000 Uani D . . . . .
H11 H -0.5712 0.1763 0.7364 0.0448 1.0000 Uiso R . . . . .
H12 H -0.5816 0.0863 0.7283 0.0451 1.0000 Uiso R . . . . .
H13 H -0.3922 0.1271 0.7519 0.0455 1.0000 Uiso R . . . . .
H21 H -0.6034 0.1441 0.6123 0.0277 1.0000 Uiso R . . . . .
H22 H -0.4064 0.1824 0.6377 0.0274 1.0000 Uiso R . . . . .
H42 H -0.3096 -0.1678 0.6145 0.0687 1.0000 Uiso R . . . . .
H41 H -0.2833 -0.0978 0.6698 0.0693 1.0000 Uiso R . . . . .
H43 H -0.1095 -0.1355 0.6450 0.0688 1.0000 Uiso R . . . . .
H51 H -0.3878 -0.0570 0.5497 0.0295 1.0000 Uiso R . . . . .
H52 H -0.2108 -0.0919 0.5263 0.0296 1.0000 Uiso R . . . . .
H91 H -0.0828 0.1578 0.7231 0.0273 1.0000 Uiso R . . . . .
H101 H 0.0982 0.2666 0.7250 0.0271 1.0000 Uiso R . . . . .
H121 H 0.0966 0.2476 0.5095 0.0238 1.0000 Uiso R . . . . .
H131 H -0.0845 0.1358 0.5074 0.0243 1.0000 Uiso R . . . . .
H151 H 0.1047 0.3797 0.5193 0.0240 1.0000 Uiso R . . . . .
H161 H 0.2758 0.4914 0.5206 0.0243 1.0000 Uiso R . . . . .
H181 H 0.5628 0.4352 0.7202 0.0243 1.0000 Uiso R . . . . .
H191 H 0.3882 0.3236 0.7186 0.0244 1.0000 Uiso R . . . . .
H222 H 0.9361 0.4766 0.6079 0.0301 1.0000 Uiso R . . . . .
H221 H 0.7719 0.4296 0.6322 0.0313 1.0000 Uiso R . . . . .
H232 H 1.0380 0.4245 0.7202 0.0506 1.0000 Uiso R . . . . .
H231 H 1.0367 0.5141 0.7268 0.0494 1.0000 Uiso R . . . . .
H233 H 0.8794 0.4645 0.7530 0.0504 1.0000 Uiso R . . . . .
H251 H 0.5405 0.7127 0.6250 0.0352 1.0000 Uiso R . . . . .
H252 H 0.6667 0.6765 0.5756 0.0332 1.0000 Uiso R . . . . .
H261 H 0.4782 0.7703 0.5109 0.0580 1.0000 Uiso R . . . . .
H262 H 0.3056 0.7200 0.5184 0.0584 1.0000 Uiso R . . . . .
H263 H 0.4474 0.6909 0.4722 0.0588 1.0000 Uiso R . . . . .
H31 H -0.458(2) 0.0308(9) 0.6143(12) 0.0259(19) 1.0000 Uiso D . . . . .
H241 H 0.344(2) 0.6086(9) 0.5989(12) 0.0253(19) 1.0000 Uiso D . . . . .
H211 H 0.788(2) 0.5849(9) 0.6319(12) 0.0236(19) 1.0000 Uiso D . . . . .
H61 H -0.038(2) 0.0015(9) 0.5848(12) 0.0255(19) 1.0000 Uiso D . . . . .
H1011 H 0.709(6) 0.3397(15) 0.8305(19) 0.087(2) 1.0000 Uiso D . . . . .
H1012 H 0.761(4) 0.2717(19) 0.8316(18) 0.087(2) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4439(6)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.512(3) yes
C1 . H11 . 0.962 no
C1 . H12 . 0.970 no
C1 . H13 . 0.957 no
C2 . N3 . 1.471(2) yes
C2 . H21 . 0.971 no
C2 . H22 . 0.960 no
N3 . C7 . 1.315(2) yes
N3 . H31 . 0.857(15) no
C4 . C5 . 1.510(3) yes
C4 . H42 . 0.963 no
C4 . H41 . 0.969 no
C4 . H43 . 0.980 no
C5 . N6 . 1.466(2) yes
C5 . H51 . 0.972 no
C5 . H52 . 0.973 no
N6 . C7 . 1.312(2) yes
N6 . H61 . 0.867(16) no
C7 . C8 . 1.492(2) yes
C8 . C9 . 1.395(3) yes
C8 . C13 . 1.389(3) yes
C9 . C10 . 1.388(3) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.395(3) yes
C10 . H101 . 0.935 no
C11 . C12 . 1.397(3) yes
C11 . C14 . 1.488(2) yes
C12 . C13 . 1.384(2) yes
C12 . H121 . 0.961 no
C13 . H131 . 0.945 no
C14 . C15 . 1.396(3) yes
C14 . C19 . 1.400(3) yes
C15 . C16 . 1.385(2) yes
C15 . H151 . 0.947 no
C16 . C17 . 1.392(3) yes
C16 . H161 . 0.953 no
C17 . C18 . 1.402(3) yes
C17 . C20 . 1.488(2) yes
C18 . C19 . 1.387(3) yes
C18 . H181 . 0.960 no
C19 . H191 . 0.947 no
C20 . N21 . 1.315(2) yes
C20 . N24 . 1.321(2) yes
N21 . C22 . 1.469(2) yes
N21 . H211 . 0.854(15) no
C22 . C23 . 1.507(3) yes
C22 . H222 . 0.977 no
C22 . H221 . 0.965 no
C23 . H232 . 0.964 no
C23 . H231 . 0.961 no
C23 . H233 . 0.972 no
N24 . C25 . 1.468(2) yes
N24 . H241 . 0.863(15) no
C25 . C26 . 1.503(3) yes
C25 . H251 . 0.951 no
C25 . H252 . 0.970 no
C26 . H261 . 0.959 no
C26 . H262 . 0.955 no
C26 . H263 . 0.970 no
O101 . H1011 . 0.827(18) no
O101 . H1012 . 0.810(18) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . H11 . 110.6 no
C2 . C1 . H12 . 111.3 no
H11 . C1 . H12 . 109.2 no
C2 . C1 . H13 . 108.6 no
H11 . C1 . H13 . 108.7 no
H12 . C1 . H13 . 108.3 no
C1 . C2 . N3 . 110.47(16) yes
C1 . C2 . H21 . 109.3 no
N3 . C2 . H21 . 108.4 no
C1 . C2 . H22 . 111.0 no
N3 . C2 . H22 . 106.2 no
H21 . C2 . H22 . 111.4 no
C2 . N3 . C7 . 126.88(16) yes
C2 . N3 . H31 . 114.8(10) no
C7 . N3 . H31 . 118.3(10) no
C5 . C4 . H42 . 108.9 no
C5 . C4 . H41 . 109.7 no
H42 . C4 . H41 . 110.5 no
C5 . C4 . H43 . 109.2 no
H42 . C4 . H43 . 109.8 no
H41 . C4 . H43 . 108.6 no
C4 . C5 . N6 . 112.09(16) yes
C4 . C5 . H51 . 108.1 no
N6 . C5 . H51 . 111.0 no
C4 . C5 . H52 . 109.1 no
N6 . C5 . H52 . 108.5 no
H51 . C5 . H52 . 107.9 no
C5 . N6 . C7 . 125.61(16) yes
C5 . N6 . H61 . 115.6(10) no
C7 . N6 . H61 . 118.5(10) no
N3 . C7 . N6 . 121.94(16) yes
N3 . C7 . C8 . 121.21(16) yes
N6 . C7 . C8 . 116.74(16) yes
C7 . C8 . C9 . 122.62(16) yes
C7 . C8 . C13 . 117.27(16) yes
C9 . C8 . C13 . 120.08(16) yes
C8 . C9 . C10 . 119.26(17) yes
C8 . C9 . H91 . 120.7 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . C11 . 121.32(17) yes
C9 . C10 . H101 . 119.1 no
C11 . C10 . H101 . 119.6 no
C10 . C11 . C12 . 118.45(16) yes
C10 . C11 . C14 . 121.39(16) yes
C12 . C11 . C14 . 120.15(16) yes
C11 . C12 . C13 . 120.75(17) yes
C11 . C12 . H121 . 118.5 no
C13 . C12 . H121 . 120.8 no
C8 . C13 . C12 . 120.12(17) yes
C8 . C13 . H131 . 119.1 no
C12 . C13 . H131 . 120.8 no
C11 . C14 . C15 . 120.30(16) yes
C11 . C14 . C19 . 121.17(16) yes
C15 . C14 . C19 . 118.53(16) yes
C14 . C15 . C16 . 120.72(16) yes
C14 . C15 . H151 . 120.3 no
C16 . C15 . H151 . 119.0 no
C15 . C16 . C17 . 120.51(17) yes
C15 . C16 . H161 . 119.8 no
C17 . C16 . H161 . 119.7 no
C16 . C17 . C18 . 119.39(16) yes
C16 . C17 . C20 . 118.79(16) yes
C18 . C17 . C20 . 121.81(16) yes
C17 . C18 . C19 . 119.74(17) yes
C17 . C18 . H181 . 119.9 no
C19 . C18 . H181 . 120.3 no
C14 . C19 . C18 . 121.10(17) yes
C14 . C19 . H191 . 120.0 no
C18 . C19 . H191 . 118.9 no
C17 . C20 . N21 . 121.24(16) yes
C17 . C20 . N24 . 116.57(16) yes
N21 . C20 . N24 . 122.15(16) yes
C20 . N21 . C22 . 127.58(15) yes
C20 . N21 . H211 . 117.4(10) no
C22 . N21 . H211 . 114.4(10) no
N21 . C22 . C23 . 111.81(16) yes
N21 . C22 . H222 . 109.7 no
C23 . C22 . H222 . 107.6 no
N21 . C22 . H221 . 107.7 no
C23 . C22 . H221 . 109.6 no
H222 . C22 . H221 . 110.4 no
C22 . C23 . H232 . 108.3 no
C22 . C23 . H231 . 109.1 no
H232 . C23 . H231 . 108.9 no
C22 . C23 . H233 . 110.3 no
H232 . C23 . H233 . 109.1 no
H231 . C23 . H233 . 111.1 no
C20 . N24 . C25 . 125.97(16) yes
C20 . N24 . H241 . 116.4(10) no
C25 . N24 . H241 . 115.9(10) no
N24 . C25 . C26 . 109.86(16) yes
N24 . C25 . H251 . 107.4 no
C26 . C25 . H251 . 112.2 no
N24 . C25 . H252 . 111.2 no
C26 . C25 . H252 . 107.9 no
H251 . C25 . H252 . 108.2 no
C25 . C26 . H261 . 109.5 no
C25 . C26 . H262 . 109.9 no
H261 . C26 . H262 . 110.4 no
C25 . C26 . H263 . 111.3 no
H261 . C26 . H263 . 107.8 no
H262 . C26 . H263 . 107.8 no
H1011 . O101 . H1012 . 99(4) no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C19 . H191 . O101 . 129 0.95 2.55 3.232(3) yes
C22 . H221 . C18 . 120 0.97 2.54 3.133(3) yes



# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 4 x .
# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Water/methanol/THF'
####################################################################### 
# 
# 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_Biphen_BPDC
_database_code_depnum_ccdc_archive 'CCDC 2503996'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2025-11-19 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_THETM01_Biphen_BPDC         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals were relatively small and weakly-diffracting. Even using 
lengthy exposure times, some high angle reflections were too weak to be 
observed.
;
_vrf_PLAT021_Biphen_BPDC         
;
PROBLEM: Ratio Unique / Expected Reflections too High ...      1.064       
RESPONSE: The fcf file contains all the merged data (   3818) 
but only   3574 of them are marked as "incl". 243 are flagged "h" i.e. 
rejected high angle reflections also marked "excl".

Checkcif/PLATON do not yet make use of the "incl" flag. 
;

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
Crystals diffracted relatively weakly and even with long exposure times, some 
reflections are quite weak.

N-H hydrogen atoms were inserted at calculated positions and then their 
positions were refined with restraints on N-H distances and C-N-H angles.

Otherwise it was not necessary to use any restraints in the refinement.

CheckCIF highlights possible additional symmetry, however this does not appear
to be genuine. There is a small amount of residual electron density, but 
this appears to be noise rather than missed solvent or disorder.
;

_cell_length_a                   10.9536(9)
_cell_length_b                   12.2674(12)
_cell_length_c                   12.3465(8)
_cell_angle_alpha                92.853(6)
_cell_angle_beta                 98.138(6)
_cell_angle_gamma                105.889(8)
_cell_volume                     1572.7(2)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C36 H40 N4 O4'
_chemical_formula_moiety         'C22 H32 N4, C14 H8 O4'
_chemical_compound_source        synthesized
_chemical_formula_weight         592.74


_cell_measurement_reflns_used    2332
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      30.64
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.14

_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             631.995
_exptl_absorpt_coefficient_mu    0.082

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip, (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13617
_diffrn_reflns_av_unetI/netI     10.183
_reflns_number_total             3818
_diffrn_reflns_av_R_equivalents  0.127

_diffrn_reflns_theta_min         2.217
# The actual theta max before filtering is 21.965 
_diffrn_reflns_theta_max         21.419
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        21.965
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   0.87
_oxford_diffrn_Wilson_scale      275.84

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.69
_refine_diff_density_max         0.73

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     16
_refine_ls_number_parameters     413
_refine_ls_number_reflns         3574
_refine_ls_R_factor_ref          0.1255
_refine_ls_wR_factor_ref         0.1489
_refine_ls_goodness_of_fit_ref   1.0221
_refine_ls_shift/su_max          0.0000930
_refine_ls_shift/su_mean         0.0000104

# Computed with I/sigma = -10 
_reflns_number_all               3574
_refine_ls_R_factor_all          0.1255
_refine_ls_wR_factor_all         0.1489

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2038
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_gt          0.1278


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.30P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.4148(5) 0.2730(5) 0.6406(4) 0.0437 1.0000 Uani . . . . . .
C2 C 0.4406(5) 0.2203(4) 0.5356(4) 0.0329 1.0000 Uani D . . . . .
N3 N 0.3371(4) 0.1189(4) 0.4875(4) 0.0315 1.0000 Uani D . . . . .
C4 C -0.0817(5) -0.0371(5) 0.3305(5) 0.0475 1.0000 Uani . . . . . .
C5 C 0.0419(5) 0.0067(5) 0.2878(4) 0.0355 1.0000 Uani D . . . . .
N6 N 0.1535(4) 0.0223(4) 0.3738(3) 0.0301 1.0000 Uani D . . . . .
C7 C 0.2413(5) 0.1181(4) 0.4103(4) 0.0240 1.0000 Uani D . . . . .
C8 C 0.2360(5) 0.2260(4) 0.3614(4) 0.0219 1.0000 Uani . . . . . .
C9 C 0.2863(5) 0.2511(4) 0.2662(4) 0.0267 1.0000 Uani . . . . . .
C10 C 0.2851(5) 0.3523(4) 0.2217(4) 0.0273 1.0000 Uani . . . . . .
C11 C 0.2347(4) 0.4311(4) 0.2708(4) 0.0252 1.0000 Uani . . . . . .
C12 C 0.1843(5) 0.4035(5) 0.3660(4) 0.0316 1.0000 Uani . . . . . .
C13 C 0.1843(5) 0.3025(4) 0.4110(4) 0.0319 1.0000 Uani . . . . . .
C14 C 0.2348(4) 0.5397(4) 0.2221(4) 0.0224 1.0000 Uani . . . . . .
C15 C 0.2539(5) 0.5553(4) 0.1137(4) 0.0299 1.0000 Uani . . . . . .
C16 C 0.2589(5) 0.6585(4) 0.0699(4) 0.0290 1.0000 Uani . . . . . .
C17 C 0.2419(4) 0.7481(4) 0.1331(4) 0.0248 1.0000 Uani . . . . . .
C18 C 0.2196(5) 0.7327(4) 0.2400(4) 0.0298 1.0000 Uani . . . . . .
C19 C 0.2172(5) 0.6307(4) 0.2830(4) 0.0272 1.0000 Uani . . . . . .
C20 C 0.2462(5) 0.8604(5) 0.0912(4) 0.0272 1.0000 Uani D . . . . .
N21 N 0.1582(4) 0.8717(3) 0.0119(3) 0.0272 1.0000 Uani D . . . . .
C22 C 0.0586(5) 0.7815(4) -0.0571(4) 0.0312 1.0000 Uani D . . . . .
C23 C 0.0968(5) 0.7605(5) -0.1679(4) 0.0397 1.0000 Uani . . . . . .
N24 N 0.3359(4) 0.9520(4) 0.1383(3) 0.0329 1.0000 Uani D . . . . .
C25 C 0.4498(5) 0.9549(5) 0.2172(4) 0.0386 1.0000 Uani D . . . . .
C26 C 0.5698(5) 0.9951(5) 0.1655(5) 0.0504 1.0000 Uani . . . . . .
O51 O 0.8376(3) 0.9154(3) 0.0289(3) 0.0403 1.0000 Uani . . . . . .
O52 O 0.6327(3) 0.8371(3) -0.0496(3) 0.0323 1.0000 Uani . . . . . .
C53 C 0.7341(6) 0.8357(5) 0.0129(4) 0.0279 1.0000 Uani . . . . . .
C54 C 0.7328(5) 0.7335(4) 0.0755(4) 0.0238 1.0000 Uani . . . . . .
C55 C 0.8473(5) 0.7203(4) 0.1289(4) 0.0296 1.0000 Uani . . . . . .
C56 C 0.8488(5) 0.6285(4) 0.1888(4) 0.0290 1.0000 Uani . . . . . .
C57 C 0.7350(5) 0.5469(4) 0.1983(4) 0.0221 1.0000 Uani . . . . . .
C58 C 0.6212(5) 0.5597(4) 0.1428(4) 0.0256 1.0000 Uani . . . . . .
C59 C 0.6207(5) 0.6502(4) 0.0811(4) 0.0257 1.0000 Uani . . . . . .
C60 C 0.7372(5) 0.4521(4) 0.2687(4) 0.0247 1.0000 Uani . . . . . .
C61 C 0.8412(5) 0.4599(4) 0.3513(4) 0.0279 1.0000 Uani . . . . . .
C62 C 0.8450(5) 0.3703(4) 0.4137(4) 0.0275 1.0000 Uani . . . . . .
C63 C 0.7450(5) 0.2702(4) 0.3979(4) 0.0232 1.0000 Uani . . . . . .
C64 C 0.6404(5) 0.2635(4) 0.3179(4) 0.0287 1.0000 Uani . . . . . .
C65 C 0.6367(5) 0.3511(4) 0.2531(4) 0.0284 1.0000 Uani . . . . . .
C66 C 0.7507(6) 0.1701(5) 0.4625(4) 0.0282 1.0000 Uani . . . . . .
O67 O 0.8516(3) 0.1787(3) 0.5295(3) 0.0343 1.0000 Uani . . . . . .
O68 O 0.6534(3) 0.0850(3) 0.4448(3) 0.0390 1.0000 Uani . . . . . .
H11 H 0.4895 0.3322 0.6760 0.0711 1.0000 Uiso R . . . . .
H12 H 0.3934 0.2159 0.6921 0.0710 1.0000 Uiso R . . . . .
H13 H 0.3433 0.3049 0.6241 0.0711 1.0000 Uiso R . . . . .
H21 H 0.5191 0.1971 0.5553 0.0496 1.0000 Uiso R . . . . .
H22 H 0.4541 0.2773 0.4819 0.0497 1.0000 Uiso R . . . . .
H41 H -0.1532 -0.0597 0.2705 0.0841 1.0000 Uiso R . . . . .
H42 H -0.0775 -0.1007 0.3715 0.0841 1.0000 Uiso R . . . . .
H43 H -0.0919 0.0242 0.3784 0.0843 1.0000 Uiso R . . . . .
H51 H 0.0454 -0.0472 0.2282 0.0463 1.0000 Uiso R . . . . .
H52 H 0.0445 0.0808 0.2592 0.0467 1.0000 Uiso R . . . . .
H91 H 0.3208 0.1992 0.2302 0.0422 1.0000 Uiso R . . . . .
H101 H 0.3175 0.3693 0.1549 0.0348 1.0000 Uiso R . . . . .
H121 H 0.1502 0.4553 0.4003 0.0449 1.0000 Uiso R . . . . .
H131 H 0.1500 0.2857 0.4773 0.0418 1.0000 Uiso R . . . . .
H151 H 0.2646 0.4940 0.0695 0.0386 1.0000 Uiso R . . . . .
H161 H 0.2757 0.6682 -0.0031 0.0377 1.0000 Uiso R . . . . .
H181 H 0.2039 0.7915 0.2837 0.0396 1.0000 Uiso R . . . . .
H191 H 0.2037 0.6211 0.3567 0.0356 1.0000 Uiso R . . . . .
H222 H -0.0213 0.8026 -0.0679 0.0455 1.0000 Uiso R . . . . .
H221 H 0.0469 0.7126 -0.0196 0.0454 1.0000 Uiso R . . . . .
H233 H 0.0249 0.7055 -0.2134 0.0690 1.0000 Uiso R . . . . .
H232 H 0.1169 0.8327 -0.2018 0.0694 1.0000 Uiso R . . . . .
H231 H 0.1708 0.7304 -0.1582 0.0693 1.0000 Uiso R . . . . .
H252 H 0.4568 1.0089 0.2817 0.0526 1.0000 Uiso R . . . . .
H251 H 0.4433 0.8782 0.2414 0.0528 1.0000 Uiso R . . . . .
H262 H 0.6447 1.0028 0.2211 0.0860 1.0000 Uiso R . . . . .
H261 H 0.5701 1.0679 0.1382 0.0863 1.0000 Uiso R . . . . .
H263 H 0.5662 0.9389 0.1065 0.0861 1.0000 Uiso R . . . . .
H551 H 0.9250 0.7758 0.1262 0.0373 1.0000 Uiso R . . . . .
H561 H 0.9281 0.6195 0.2246 0.0396 1.0000 Uiso R . . . . .
H581 H 0.5421 0.5049 0.1485 0.0358 1.0000 Uiso R . . . . .
H591 H 0.5428 0.6563 0.0423 0.0393 1.0000 Uiso R . . . . .
H611 H 0.9112 0.5293 0.3641 0.0367 1.0000 Uiso R . . . . .
H621 H 0.9178 0.3756 0.4676 0.0386 1.0000 Uiso R . . . . .
H641 H 0.5685 0.1970 0.3086 0.0387 1.0000 Uiso R . . . . .
H651 H 0.5654 0.3426 0.1983 0.0388 1.0000 Uiso R . . . . .
H61 H 0.161(3) -0.0394(18) 0.404(3) 0.040(2) 1.0000 Uiso D . . . . .
H31 H 0.338(3) 0.0535(18) 0.512(3) 0.042(2) 1.0000 Uiso D . . . . .
H211 H 0.163(3) 0.9438(17) -0.002(3) 0.039(2) 1.0000 Uiso D . . . . .
H241 H 0.339(3) 1.014(2) 0.106(3) 0.042(2) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.09064(4)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.516(7) yes
C1 . H11 . 0.964 no
C1 . H12 . 0.972 no
C1 . H13 . 0.969 no
C2 . N3 . 1.466(6) yes
C2 . H21 . 0.980 no
C2 . H22 . 0.983 no
N3 . C7 . 1.311(6) yes
N3 . H31 . 0.876(19) no
C4 . C5 . 1.494(7) yes
C4 . H41 . 0.967 no
C4 . H42 . 0.959 no
C4 . H43 . 0.974 no
C5 . N6 . 1.464(6) yes
C5 . H51 . 0.976 no
C5 . H52 . 0.985 no
N6 . C7 . 1.310(6) yes
N6 . H61 . 0.878(19) no
C7 . C8 . 1.494(7) yes
C8 . C9 . 1.380(7) yes
C8 . C13 . 1.382(7) yes
C9 . C10 . 1.385(7) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.391(7) yes
C10 . H101 . 0.953 no
C11 . C12 . 1.387(7) yes
C11 . C14 . 1.488(7) yes
C12 . C13 . 1.383(7) yes
C12 . H121 . 0.933 no
C13 . H131 . 0.956 no
C14 . C15 . 1.398(7) yes
C14 . C19 . 1.387(6) yes
C15 . C16 . 1.392(7) yes
C15 . H151 . 0.950 no
C16 . C17 . 1.385(7) yes
C16 . H161 . 0.952 no
C17 . C18 . 1.389(7) yes
C17 . C20 . 1.487(7) yes
C18 . C19 . 1.377(7) yes
C18 . H181 . 0.947 no
C19 . H191 . 0.951 no
C20 . N21 . 1.314(6) yes
C20 . N24 . 1.317(6) yes
N21 . C22 . 1.457(6) yes
N21 . H211 . 0.899(19) no
C22 . C23 . 1.515(7) yes
C22 . H222 . 0.973 no
C22 . H221 . 0.970 no
C23 . H233 . 0.968 no
C23 . H232 . 0.982 no
C23 . H231 . 0.974 no
N24 . C25 . 1.461(6) yes
N24 . H241 . 0.868(19) no
C25 . C26 . 1.515(7) yes
C25 . H252 . 0.990 no
C25 . H251 . 0.988 no
C26 . H262 . 0.972 no
C26 . H261 . 0.970 no
C26 . H263 . 0.966 no
O51 . C53 . 1.261(6) yes
O52 . C53 . 1.265(6) yes
C53 . C54 . 1.503(7) yes
C54 . C55 . 1.387(6) yes
C54 . C59 . 1.379(7) yes
C55 . C56 . 1.380(7) yes
C55 . H551 . 0.939 no
C56 . C57 . 1.393(7) yes
C56 . H561 . 0.955 no
C57 . C58 . 1.387(6) yes
C57 . C60 . 1.488(7) yes
C58 . C59 . 1.378(7) yes
C58 . H581 . 0.955 no
C59 . H591 . 0.942 no
C60 . C61 . 1.397(6) yes
C60 . C65 . 1.398(7) yes
C61 . C62 . 1.380(7) yes
C61 . H611 . 0.965 no
C62 . C63 . 1.386(7) yes
C62 . H621 . 0.950 no
C63 . C64 . 1.384(6) yes
C63 . C66 . 1.508(7) yes
C64 . C65 . 1.377(7) yes
C64 . H641 . 0.955 no
C65 . H651 . 0.937 no
C66 . O67 . 1.259(6) yes
C66 . O68 . 1.254(6) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . H11 . 111.0 no
C2 . C1 . H12 . 110.6 no
H11 . C1 . H12 . 107.8 no
C2 . C1 . H13 . 109.7 no
H11 . C1 . H13 . 109.1 no
H12 . C1 . H13 . 108.7 no
C1 . C2 . N3 . 112.9(4) yes
C1 . C2 . H21 . 106.5 no
N3 . C2 . H21 . 108.0 no
C1 . C2 . H22 . 109.5 no
N3 . C2 . H22 . 109.9 no
H21 . C2 . H22 . 109.9 no
C2 . N3 . C7 . 125.2(4) yes
C2 . N3 . H31 . 118.0(13) no
C7 . N3 . H31 . 116.8(13) no
C5 . C4 . H41 . 110.5 no
C5 . C4 . H42 . 109.2 no
H41 . C4 . H42 . 110.1 no
C5 . C4 . H43 . 107.6 no
H41 . C4 . H43 . 109.6 no
H42 . C4 . H43 . 109.9 no
C4 . C5 . N6 . 111.8(4) yes
C4 . C5 . H51 . 108.8 no
N6 . C5 . H51 . 109.6 no
C4 . C5 . H52 . 108.8 no
N6 . C5 . H52 . 108.6 no
H51 . C5 . H52 . 109.4 no
C5 . N6 . C7 . 126.7(4) yes
C5 . N6 . H61 . 115.8(13) no
C7 . N6 . H61 . 117.5(13) no
N3 . C7 . N6 . 119.9(5) yes
N3 . C7 . C8 . 119.6(5) yes
N6 . C7 . C8 . 120.4(5) yes
C7 . C8 . C9 . 119.5(5) yes
C7 . C8 . C13 . 121.2(5) yes
C9 . C8 . C13 . 119.3(5) yes
C8 . C9 . C10 . 120.0(5) yes
C8 . C9 . H91 . 120.6 no
C10 . C9 . H91 . 119.4 no
C9 . C10 . C11 . 121.7(5) yes
C9 . C10 . H101 . 120.5 no
C11 . C10 . H101 . 117.7 no
C10 . C11 . C12 . 117.0(5) yes
C10 . C11 . C14 . 121.0(4) yes
C12 . C11 . C14 . 122.0(5) yes
C11 . C12 . C13 . 121.8(5) yes
C11 . C12 . H121 . 118.4 no
C13 . C12 . H121 . 119.8 no
C12 . C13 . C8 . 120.1(5) yes
C12 . C13 . H131 . 120.3 no
C8 . C13 . H131 . 119.6 no
C11 . C14 . C15 . 121.8(4) yes
C11 . C14 . C19 . 121.3(4) yes
C15 . C14 . C19 . 116.9(5) yes
C14 . C15 . C16 . 121.5(5) yes
C14 . C15 . H151 . 118.9 no
C16 . C15 . H151 . 119.6 no
C15 . C16 . C17 . 120.1(5) yes
C15 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C18 . 118.9(5) yes
C16 . C17 . C20 . 122.7(5) yes
C18 . C17 . C20 . 118.4(5) yes
C17 . C18 . C19 . 120.4(5) yes
C17 . C18 . H181 . 120.4 no
C19 . C18 . H181 . 119.2 no
C14 . C19 . C18 . 122.1(5) yes
C14 . C19 . H191 . 117.7 no
C18 . C19 . H191 . 120.1 no
C17 . C20 . N21 . 121.5(5) yes
C17 . C20 . N24 . 119.5(5) yes
N21 . C20 . N24 . 118.8(5) yes
C20 . N21 . C22 . 127.5(4) yes
C20 . N21 . H211 . 115.3(13) no
C22 . N21 . H211 . 117.2(13) no
N21 . C22 . C23 . 111.2(4) yes
N21 . C22 . H222 . 109.4 no
C23 . C22 . H222 . 109.4 no
N21 . C22 . H221 . 107.9 no
C23 . C22 . H221 . 109.3 no
H222 . C22 . H221 . 109.7 no
C22 . C23 . H233 . 108.4 no
C22 . C23 . H232 . 108.5 no
H233 . C23 . H232 . 109.8 no
C22 . C23 . H231 . 109.7 no
H233 . C23 . H231 . 109.5 no
H232 . C23 . H231 . 110.9 no
C20 . N24 . C25 . 126.5(4) yes
C20 . N24 . H241 . 115.8(14) no
C25 . N24 . H241 . 115.2(14) no
N24 . C25 . C26 . 110.2(4) yes
N24 . C25 . H252 . 109.5 no
C26 . C25 . H252 . 108.2 no
N24 . C25 . H251 . 110.0 no
C26 . C25 . H251 . 109.4 no
H252 . C25 . H251 . 109.4 no
C25 . C26 . H262 . 108.8 no
C25 . C26 . H261 . 107.3 no
H262 . C26 . H261 . 110.9 no
C25 . C26 . H263 . 108.1 no
H262 . C26 . H263 . 110.4 no
H261 . C26 . H263 . 111.3 no
O52 . C53 . O51 . 124.8(5) yes
O52 . C53 . C54 . 118.7(5) yes
O51 . C53 . C54 . 116.5(5) yes
C53 . C54 . C55 . 119.8(5) yes
C53 . C54 . C59 . 122.2(5) yes
C55 . C54 . C59 . 117.9(5) yes
C54 . C55 . C56 . 121.1(5) yes
C54 . C55 . H551 . 119.6 no
C56 . C55 . H551 . 119.3 no
C55 . C56 . C57 . 121.0(5) yes
C55 . C56 . H561 . 120.6 no
C57 . C56 . H561 . 118.4 no
C56 . C57 . C58 . 117.5(4) yes
C56 . C57 . C60 . 120.4(4) yes
C58 . C57 . C60 . 122.1(4) yes
C57 . C58 . C59 . 121.3(5) yes
C57 . C58 . H581 . 118.8 no
C59 . C58 . H581 . 119.9 no
C54 . C59 . C58 . 121.2(5) yes
C54 . C59 . H591 . 118.7 no
C58 . C59 . H591 . 120.1 no
C57 . C60 . C61 . 121.2(5) yes
C57 . C60 . C65 . 121.4(4) yes
C61 . C60 . C65 . 117.4(5) yes
C60 . C61 . C62 . 121.0(5) yes
C60 . C61 . H611 . 118.8 no
C62 . C61 . H611 . 120.2 no
C61 . C62 . C63 . 121.4(5) yes
C61 . C62 . H621 . 120.1 no
C63 . C62 . H621 . 118.6 no
C62 . C63 . C64 . 117.7(5) yes
C62 . C63 . C66 . 121.7(5) yes
C64 . C63 . C66 . 120.5(5) yes
C63 . C64 . C65 . 121.6(5) yes
C63 . C64 . H641 . 119.0 no
C65 . C64 . H641 . 119.4 no
C60 . C65 . C64 . 120.9(5) yes
C60 . C65 . H651 . 119.9 no
C64 . C65 . H651 . 119.2 no
C63 . C66 . O67 . 117.7(5) yes
C63 . C66 . O68 . 116.7(5) yes
O67 . C66 . O68 . 125.6(5) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O52 2_665 137 0.95 2.40 3.166(7) yes
C18 . H181 . O67 2_666 138 0.95 2.50 3.266(7) yes
C26 . H263 . O52 . 160 0.97 2.54 3.466(7) yes
N6 . H61 . O67 2_656 171(4) 0.878(19) 1.91(2) 2.783(7) yes
N3 . H31 . O68 2_656 176(5) 0.876(19) 1.83(2) 2.701(7) yes
N21 . H211 . O51 2_675 176(4) 0.899(19) 1.78(2) 2.674(7) yes
N24 . H241 . O52 2_675 172.3(19) 0.868(19) 1.95(2) 2.814(7) yes



# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-2 1 2 x .
# end of ARCHIVE-HKL.CIF 

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_Biphen_TP
_database_code_depnum_ccdc_archive 'CCDC 2503995'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2025-11-19 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT082_Biphen_TP           
;
PROBLEM: High R1 Value ..................................       0.18 Report
RESPONSE: Data are of limited quality. While the molecular structure and 
packing can be determined unambigously, detailed inferences about bond lengths
and hydrogen bonding parameters should not be drawn.
;
_vrf_PLAT990_Biphen_TP           
;
PROBLEM: Deprecated .res/.hkl Input Style SQUEEZE Job ...          ! Note  
RESPONSE: PLATON-SQUEEZE was implemented within the CRYSTALS suite, which does
not use .ins/.res files.
;

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
;Crystals diffracted relatively weakly and even with long exposure times, some 
reflections are quite weak. The space group was quite ambiguous and it was 
initially difficult to solve the structure. Overall, the data are of limited
quality, so while the overall molecular structure and packing can be 
determined unambiguously, detailed inferences should not be drawn about bond
lengths or hydrogen bonding parameters.

The structure contains diffuse electron density, which appears to arise from
disordered solvent molecules. This could not be resolved and so PLATON-SQUEEZE
was used to include this electron density in the refinement. 

The ethyl groups of the diethylamidinium moities are disordered. This was 
modelled by having two positions for each terminal CH3 group (relative
occupancies: 0.75:0.25 for one group and 0.5:0.50 for the other), with 
restraints applied to the bond lengths and angles of the diethylamidinium 
groups. Thermal and vibrational ellipsoid restraints were used on all atoms of 
the diamidinium molecule, with CRYSTALS QISO restraints (similar to SHELX ISOR 
restraints) used on the atoms of the disordered ethyl groups. The terephthalate
anion was better-behaved, but it was necessary to use restraints on the C-C
bonds between the phenyl rings and the carboxylate groups.

C-H and N-H hydrogen atoms were inserted at calculated positions (N-H distances
= 0.86 A), and these positions used as the basis for a riding model.,SQUEEZE
;

_cell_length_a                   9.4959(13)
_cell_length_b                   17.181(2)
_cell_length_c                   23.879(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3895.8(8)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n n a '
_symmetry_space_group_name_Hall  '-P 2a 2bc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2
-x+1/2,-y,z
x+1/2,y,-z
x,-y+1/2,-z+1/2
-x,y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C30 H36 N4 O4'
_chemical_formula_moiety         'C22 H32 N, C8 H4 O4'
_chemical_compound_source        synthesized
_chemical_formula_weight         516.64


_cell_measurement_reflns_used    2431
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.83
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.50

_exptl_crystal_density_diffrn    0.881
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.059

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SHELXT, (Sheldrick, 2015)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            19786
_diffrn_reflns_av_unetI/netI     9.601
_reflns_number_total             3580
_diffrn_reflns_av_R_equivalents  0.150

_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         25.349
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.349
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              0
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   3.30
_oxford_diffrn_Wilson_scale      209.87

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.75
_refine_diff_density_max         0.79

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     223
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3580
_refine_ls_R_factor_ref          0.2583
_refine_ls_wR_factor_ref         0.2336
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0000915
_refine_ls_shift/su_mean         0.0000085

# Computed with I/sigma = -10 
_reflns_number_all               3580
_refine_ls_R_factor_all          0.2583
_refine_ls_wR_factor_all         0.2336

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1694
_refine_ls_R_factor_gt           0.1848
_refine_ls_wR_factor_gt          0.2268


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Quasi-Unit weights 
 W = 1.0 or 1./4Fsq 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.4795(14) 0.3613(9) 0.4578(7) 0.1447 0.7500 Uani D U . . 1 .
C2 C 0.6262(13) 0.3709(6) 0.4404(4) 0.1159 1.0000 Uani D U . . . .
N3 N 0.6852(9) 0.4431(4) 0.4649(3) 0.0977 1.0000 Uani D U . . . .
C4 C 0.7500 0.5000 0.4379(4) 0.0829 1.0000 Uani DS TU . . . .
C5 C 0.7500 0.5000 0.3750(3) 0.0729 1.0000 Uani DS TU . . . .
C6 C 0.6296(8) 0.5244(5) 0.3458(3) 0.0795 1.0000 Uani D U . . . .
C7 C 0.6294(7) 0.5239(5) 0.2866(2) 0.0607 1.0000 Uani D U . . . .
C8 C 0.7500 0.5000 0.2580(4) 0.0543 1.0000 Uani DS TU . . . .
C9 C 0.7500 0.5000 0.1958(4) 0.0575 1.0000 Uani DS TU . . . .
C10 C 0.6293(7) 0.4804(5) 0.1661(2) 0.0614 1.0000 Uani D U . . . .
C11 C 0.6286(8) 0.4797(5) 0.1076(3) 0.0723 1.0000 Uani D U . . . .
C12 C 0.7500 0.5000 0.0780(3) 0.0625 1.0000 Uani DS TU . . . .
C13 C 0.7500 0.5000 0.0159(3) 0.0637 1.0000 Uani DS TU . . . .
N14 N 0.7809(8) 0.4353(3) -0.0113(2) 0.0669 1.0000 Uani D U . . . .
C15 C 0.8192(11) 0.3595(4) 0.0135(4) 0.0868 1.0000 Uani D U . . . .
C16 C 0.9767(14) 0.3493(9) 0.0104(7) 0.0854 0.5000 Uani D U . . 3 .
O51 O 0.6947(9) 0.4429(4) 0.5823(2) 0.1098 1.0000 Uani . . . . . .
C52 C 0.7500 0.5000 0.6065(4) 0.0697 1.0000 Uani DS T . . . .
C53 C 0.7500 0.5000 0.6689(4) 0.0773 1.0000 Uani DS T . . . .
C54 C 0.7301(9) 0.5693(5) 0.6991(3) 0.0592 1.0000 Uani . . . . . .
C55 C 0.7262(10) 0.5699(5) 0.7573(3) 0.0559 1.0000 Uani . . . . . .
C56 C 0.7500 0.5000 0.7865(3) 0.0429 1.0000 Uani DS T . . . .
C57 C 0.7500 0.5000 0.8493(4) 0.0450 1.0000 Uani DS T . . . .
O58 O 0.7169(7) 0.5617(3) 0.8741(2) 0.0671 1.0000 Uani . . . . . .
C101 C 0.738(3) 0.3079(15) 0.437(2) 0.1911 0.2500 Uani D U . . 2 .
C116 C 0.889(2) 0.3035(9) -0.0272(7) 0.1096 0.5000 Uani D U . . 4 .
H11 H 0.4396 0.3151 0.4426 0.1828 0.7500 Uiso R . . . 1 .
H12 H 0.4735 0.3597 0.4975 0.1828 0.7500 Uiso R . . . 1 .
H13 H 0.4294 0.4052 0.4442 0.1828 0.7500 Uiso R . . . 1 .
H61 H 0.5477 0.5401 0.3657 0.0823 1.0000 Uiso R . . . . .
H71 H 0.5492 0.5425 0.2669 0.0759 1.0000 Uiso R . . . . .
H101 H 0.5464 0.4668 0.1860 0.0745 1.0000 Uiso R . . . . .
H111 H 0.5456 0.4656 0.0878 0.0761 1.0000 Uiso R . . . . .
H161 H 0.9996 0.3007 0.0271 0.1480 0.5000 Uiso R . . . 3 .
H162 H 1.0230 0.3900 0.0301 0.1480 0.5000 Uiso R . . . 3 .
H163 H 1.0064 0.3494 -0.0276 0.1480 0.5000 Uiso R . . . 3 .
H541 H 0.7140 0.6166 0.6794 0.0670 1.0000 Uiso R . . . . .
H551 H 0.7157 0.6173 0.7773 0.0661 1.0000 Uiso R . . . . .
H1011 H 0.8247 0.3298 0.4250 0.2110 0.2500 Uiso R . . . 2 .
H1012 H 0.7508 0.2845 0.4729 0.2110 0.2500 Uiso R . . . 2 .
H1013 H 0.7083 0.2695 0.4111 0.2110 0.2500 Uiso R . . . 2 .
H1161 H 0.9106 0.2555 -0.0096 0.1407 0.5000 Uiso R . . . 4 .
H1162 H 0.9731 0.3293 -0.0376 0.1407 0.5000 Uiso R . . . 4 .
H1163 H 0.8333 0.2939 -0.0597 0.1407 0.5000 Uiso R . . . 4 .
H21 H 0.6751 0.3268 0.4528 0.1304 0.7500 Uiso . . . . 1 .
H22 H 0.6296 0.3750 0.4009 0.1304 0.7500 Uiso . . . . 1 .
H23 H 0.5453 0.3562 0.4623 0.1304 0.2500 Uiso . . . . 2 .
H24 H 0.5951 0.3827 0.4034 0.1304 0.2500 Uiso . . . . 2 .
H151 H 0.7942 0.3592 0.0523 0.1075 0.5000 Uiso . . . . 3 .
H152 H 0.7663 0.3194 -0.0050 0.1075 0.5000 Uiso . . . . 3 .
H153 H 0.8852 0.3672 0.0423 0.1075 0.5000 Uiso . . . . 4 .
H154 H 0.7348 0.3371 0.0292 0.1075 0.5000 Uiso . . . . 4 .
H31 H 0.6814 0.4472 0.5008 0.1332 1.0000 Uiso R . . . . .
H141 H 0.7801 0.4378 -0.0472 0.0951 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.11205(8)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.463(9) yes
C1 . H11 . 0.950 no
C1 . H12 . 0.950 no
C1 . H13 . 0.950 no
C2 . N3 . 1.481(8) yes
N3 . C4 . 1.323(6) yes
N3 . H31 . 0.860 no
C4 . C5 . 1.502(8) yes
C5 . C6 5_665 1.403(7) yes
C5 . C6 . 1.403(7) yes
C6 . C7 . 1.416(7) yes
C6 . H61 . 0.950 no
C7 . C8 . 1.395(6) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.485(11) yes
C9 . C10 5_665 1.389(7) yes
C9 . C10 . 1.389(7) yes
C10 . C11 . 1.397(7) yes
C10 . H101 . 0.950 no
C11 . C12 . 1.396(7) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.483(8) yes
C13 . N14 5_665 1.321(6) yes
C13 . N14 . 1.321(6) yes
N14 . C15 . 1.475(7) yes
N14 . H141 . 0.860 no
C16 . H161 . 0.950 no
C16 . H162 . 0.950 no
C16 . H163 . 0.950 no
O51 . C52 . 1.253(7) yes
C52 . C53 . 1.490(8) yes
C53 . C54 5_665 1.404(9) yes
C53 . C54 . 1.404(9) yes
C54 . C55 . 1.391(8) yes
C54 . H541 . 0.950 no
C55 . C56 . 1.407(9) yes
C55 . H551 . 0.950 no
C56 . C57 . 1.502(8) yes
C57 . O58 5_665 1.254(6) yes
C57 . O58 . 1.254(6) yes
C101 . H1011 . 0.950 no
C101 . H1012 . 0.950 no
C101 . H1013 . 0.950 no
C116 . H1161 . 0.950 no
C116 . H1162 . 0.950 no
C116 . H1163 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . H11 . 111.4 no
C2 . C1 . H12 . 110.1 no
H11 . C1 . H12 . 109.5 no
C2 . C1 . H13 . 106.8 no
H11 . C1 . H13 . 109.5 no
H12 . C1 . H13 . 109.5 no
C2 . N3 . C4 . 127.0(7) yes
C2 . N3 . H31 . 116.5 no
C4 . N3 . H31 . 116.4 no
N3 . C4 . N3 5_665 121.7(9) yes
N3 . C4 . C5 . 119.1(5) yes
N3 5_665 C4 . C5 . 119.1(5) yes
C4 . C5 . C6 5_665 119.8(4) yes
C4 . C5 . C6 . 119.8(4) yes
C6 5_665 C5 . C6 . 120.4(7) yes
C5 . C6 . C7 . 119.7(6) yes
C5 . C6 . H61 . 120.2 no
C7 . C6 . H61 . 120.0 no
C6 . C7 . C8 . 119.3(6) yes
C6 . C7 . H71 . 119.6 no
C8 . C7 . H71 . 121.0 no
C7 . C8 . C7 5_665 121.4(8) yes
C7 . C8 . C9 . 119.3(4) yes
C7 5_665 C8 . C9 . 119.3(4) yes
C8 . C9 . C10 5_665 120.7(4) yes
C8 . C9 . C10 . 120.7(4) yes
C10 5_665 C9 . C10 . 118.5(8) yes
C9 . C10 . C11 . 121.1(6) yes
C9 . C10 . H101 . 119.1 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 120.0(6) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.8 no
C11 . C12 . C11 5_665 119.3(8) yes
C11 . C12 . C13 . 120.4(4) yes
C11 5_665 C12 . C13 . 120.4(4) yes
C12 . C13 . N14 5_665 119.4(4) yes
C12 . C13 . N14 . 119.4(4) yes
N14 5_665 C13 . N14 . 121.1(8) yes
C13 . N14 . C15 . 126.9(6) yes
C13 . N14 . H141 . 116.5 no
C15 . N14 . H141 . 116.6 no
C15 . C16 . H161 . 108.0 no
C15 . C16 . H162 . 110.5 no
H161 . C16 . H162 . 109.5 no
C15 . C16 . H163 . 109.9 no
H161 . C16 . H163 . 109.5 no
H162 . C16 . H163 . 109.5 no
O51 5_665 C52 . O51 . 125.2(10) yes
O51 5_665 C52 . C53 . 117.4(5) yes
O51 . C52 . C53 . 117.4(5) yes
C52 . C53 . C54 5_665 120.9(5) yes
C52 . C53 . C54 . 120.9(5) yes
C54 5_665 C53 . C54 . 118.3(9) yes
C53 . C54 . C55 . 121.5(9) yes
C53 . C54 . H541 . 119.6 no
C55 . C54 . H541 . 118.8 no
C54 . C55 . C56 . 119.0(9) yes
C54 . C55 . H551 . 120.9 no
C56 . C55 . H551 . 119.9 no
C55 . C56 . C55 5_665 120.6(8) yes
C55 . C56 . C57 . 119.7(4) yes
C55 5_665 C56 . C57 . 119.7(4) yes
C56 . C57 . O58 5_665 118.2(4) yes
C56 . C57 . O58 . 118.2(4) yes
O58 5_665 C57 . O58 . 123.6(9) yes
C2 . C101 . H1011 . 109.7 no
C2 . C101 . H1012 . 110.1 no
H1011 . C101 . H1012 . 109.5 no
C2 . C101 . H1013 . 108.6 no
H1011 . C101 . H1013 . 109.5 no
H1012 . C101 . H1013 . 109.5 no
C15 . C116 . H1161 . 111.2 no
C15 . C116 . H1162 . 103.8 no
H1161 . C116 . H1162 . 109.5 no
C15 . C116 . H1163 . 113.2 no
H1161 . C116 . H1163 . 109.5 no
H1162 . C116 . H1163 . 109.5 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C1 . H11 . C116 3_455 137 0.95 2.22 2.982(11) yes
C1 . H13 . O51 6_456 140 0.95 2.41 3.193(11) yes
C101 . H1012 . C15 7_555 123 0.95 2.58 3.202(11) yes
C101 . H1012 . C116 7_555 146 0.95 2.38 3.214(11) yes
C116 . H1161 . C1 3_554 133 0.95 2.25 2.982(11) yes
C101 . H21 . C1 . 153 0.78 1.95 2.668(11) yes
C101 . H21 . C2 . 125 0.78 0.94 1.520(11) yes
N3 . H31 . O51 . 171 0.86 1.95 2.806(11) yes
N14 . H141 . O58 5_664 177 0.86 1.88 2.737(11) yes

# end of ARCHIVE-HKL.CIF 
# looking for PLATON_SQD.SQF 

# SQUEEZE RESULTS (Version = 210723) 
# Note: Data are Listed for all Voids in the P1 Unit Cell 
# i.e. Centre of Gravity, Solvent Accessible Volume, 
# Recovered number of Electrons in the Void and 
# Details about the Squeezed Material 
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.099 0.250 0.250 306 97 ' '
2 -0.006 0.250 0.750 306 97 ' '
3 0.040 0.750 0.750 306 97 ' '
4 -0.091 0.750 0.250 306 97 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
# end of PLATON_SQD.SQF 

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_Tetra_tetra
_database_code_depnum_ccdc_archive 'CCDC 2503998'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2025-11-19 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_THETM01_Tetra_tetra         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals were large but appeared to lose solvent very rapidly. Even 
working as quickly as possible to minimise solvent loss, diffraction was of 
limited quality and no diffraction could be obtained beyond 0.95 A. This, and 
the presence of relatively large voids filled with diffuse electron density 
mean the structure is of relatively low quality. Nevertheless, the molecular 
structure and packing can be determined unambigiously.
;
_vrf_PLAT021_Tetra_tetra         
;
PROBLEM: Ratio Unique / Expected Reflections too High ...      1.209       
RESPONSE: The fcf file contains all the merged data (13143) 
but only  10868 of them are marked as "incl". 2271 are flagged "h" i.e. 
rejected high angle reflections also marked "excl".
This information is embedded as a #comment  at the end of the fcf file.  
Checkcif/PLATON do not yet make use of the "incl" flag 
;
_vrf_PLAT082_Tetra_tetra         
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals were large but appeared to lose solvent very rapidly. Even 
working as quickly as possible to minimise solvent loss, diffraction was of 
limited quality and no diffraction could be obtained beyond 0.95 A. This, and 
the presence of relatively large voids filled with diffuse electron density 
mean the structure is of relatively low quality. Nevertheless, the molecular 
structure and packing can be determined unambigiously.
;
_vrf_PLAT230_Tetra_tetra         
;
PROBLEM: Hirshfeld Test Diff for    C122     --C123     .        9.2 s.u.  
RESPONSE: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals were large but appeared to lose solvent very rapidly. Even 
working as quickly as possible to minimise solvent loss, diffraction was of 
limited quality and no diffraction could be obtained beyond 0.95 A. This, and 
the presence of relatively large voids filled with diffuse electron density 
mean the structure is of relatively low quality. Nevertheless, the molecular 
structure and packing can be determined unambigiously.
;
_vrf_PLAT234_Tetra_tetra         
;
PROBLEM: Large Hirshfeld Difference C24      --C25      .       0.26 Ang.  
RESPONSE: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals were large but appeared to lose solvent very rapidly. Even 
working as quickly as possible to minimise solvent loss, diffraction was of 
limited quality and no diffraction could be obtained beyond 0.95 A. This, and 
the presence of relatively large voids filled with diffuse electron density 
mean the structure is of relatively low quality. Nevertheless, the molecular 
structure and packing can be determined unambigiously.
;
_vrf_PLAT340_Tetra_tetra         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01782 Ang.  
RESPONSE: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals were large but appeared to lose solvent very rapidly. Even 
working as quickly as possible to minimise solvent loss, diffraction was of 
limited quality and no diffraction could be obtained beyond 0.95 A. This, and 
the presence of relatively large voids filled with diffuse electron density 
mean the structure is of relatively low quality. Nevertheless, the molecular 
structure and packing can be determined unambigiously.
;
_vrf_PLAT990_Tetra_tetra         
;
PROBLEM: Deprecated .res/.hkl Input Style SQUEEZE Job ...          ! Note  
RESPONSE: PLATON-SQUEEZE was implemented within the CRYSTALS suite, which does
not use .ins/.res files.
;

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
;Crystals were large but appeared to lose solvent very rapidly. Even working
as quickly as possible to minimise solvent loss, diffraction was of limited
quality and no diffraction could be obtained beyond 0.95 A. This, and the 
presence of relatively large voids filled with diffuse electron density mean
the structure is of relatively low quality. Nevertheless, the molecular 
structure and packing can be determined unambigiously.

The diffuse electron density was included in the solvent using PLATON-SQUEEZE.
It was necessary to add restraints to all C-C and C-N bond lengths as well as
some phenyl ring C-C-C angles in order to achieve a sensible refinement. 
Restraints were added to thermal and vibrational ellipsoid parameters. 

Due to the limited quality of the data, all hydrogen atoms were inserted at 
calculated positions and ride on the attached non-H atoms (C-H distances = 
0.95 A, N-H distances = 0.86 A).,SQUEEZE
;

_cell_length_a                   30.0803(5)
_cell_length_b                   26.6383(5)
_cell_length_c                   26.8475(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     21512.6(7)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n '
_symmetry_space_group_name_Hall  '-P 2n 2ab'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,-y+1/2,z+1/2
x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z
-x,y,-z+1/2
x,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

_chemical_formula_sum            'C74 H80 N8 O8'
_chemical_formula_moiety         'C45 H64 N8, C29 H16 O8'
_chemical_compound_source        synthesized
_chemical_formula_weight         1209.50


_cell_measurement_reflns_used    19703
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      47.26
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_max          0.60

_exptl_crystal_density_diffrn    0.747
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             5152
_exptl_absorpt_coefficient_mu    0.391

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'ShelXT, (Sheldrick, 2015)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            88872
_diffrn_reflns_av_unetI/netI     3.185
_reflns_number_total             13143
_diffrn_reflns_av_R_equivalents  0.0561

_diffrn_reflns_theta_min         2.215
# The actual theta max before filtering is 54.242 
_diffrn_reflns_theta_max         49.607
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        54.242
_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              0
_reflns_limit_h_max              31
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   7.55
_oxford_diffrn_Wilson_scale      205.03

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.56

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     374
_refine_ls_number_parameters     811
_refine_ls_number_reflns         10868
_refine_ls_R_factor_ref          0.1980
_refine_ls_wR_factor_ref         0.2157
_refine_ls_goodness_of_fit_ref   1.0112
_refine_ls_shift/su_max          0.0002102
_refine_ls_shift/su_mean         0.0000209

# Computed with I/sigma = -10 
_reflns_number_all               10868
_refine_ls_R_factor_all          0.1980
_refine_ls_wR_factor_all         0.2157

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6552
_refine_ls_R_factor_gt           0.1620
_refine_ls_wR_factor_gt          0.2120


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Quasi-Unit weights 
 W = 1.0 or 1./4Fsq 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.7473(4) 0.7819(4) 0.5023(5) 0.1351 1.0000 Uani D . . . . .
C2 C 0.7352(4) 0.7263(4) 0.5069(5) 0.1236 1.0000 Uani D . . . . .
C3 C 0.7543(4) 0.6885(5) 0.4785(4) 0.1475 1.0000 Uani D . . . . .
C4 C 0.7468(5) 0.6377(5) 0.4861(5) 0.1648 1.0000 Uani D . . . . .
C5 C 0.7155(4) 0.6256(4) 0.5222(6) 0.1508 1.0000 Uani D U . . . .
C6 C 0.6965(4) 0.6621(5) 0.5522(5) 0.1658 1.0000 Uani D . . . . .
C7 C 0.7060(4) 0.7127(5) 0.5446(5) 0.1649 1.0000 Uani D . . . . .
C8 C 0.7063(4) 0.5719(4) 0.5325(7) 0.2106 1.0000 Uani D U . . . .
N9 N 0.7411(3) 0.5465(3) 0.5479(4) 0.2021 1.0000 Uani D U . . . .
C10 C 0.7405(4) 0.4934(3) 0.5608(5) 0.2366 1.0000 Uani D U . . . .
C11 C 0.7785(5) 0.4845(5) 0.5972(6) 0.3378 1.0000 Uani D U . . . .
N12 N 0.6664(3) 0.5529(4) 0.5284(5) 0.2510 1.0000 Uani D U . . . .
C13 C 0.6266(4) 0.5815(6) 0.5145(6) 0.2999 1.0000 Uani D U . . . .
C14 C 0.5961(4) 0.5813(6) 0.5597(7) 0.3623 1.0000 Uani D U . . . .
C22 C 0.7836(4) 0.7904(4) 0.4633(6) 0.1302 1.0000 Uani D . . . . .
C23 C 0.8258(4) 0.8085(4) 0.4758(5) 0.1563 1.0000 Uani D . . . . .
C24 C 0.8543(4) 0.8140(5) 0.4350(6) 0.1550 1.0000 Uani D . . . . .
C25 C 0.8458(4) 0.8059(5) 0.3847(6) 0.1652 1.0000 Uani D U . . . .
C26 C 0.8024(5) 0.7906(5) 0.3733(5) 0.1625 1.0000 Uani D . . . . .
C27 C 0.7742(4) 0.7851(5) 0.4130(6) 0.1524 1.0000 Uani D . . . . .
C28 C 0.8799(5) 0.8197(5) 0.3461(7) 0.2267 1.0000 Uani D U . . . .
N29 N 0.8922(4) 0.8685(5) 0.3472(5) 0.2550 1.0000 Uani D U . . . .
C30 C 0.9248(5) 0.8849(6) 0.3095(5) 0.3065 1.0000 Uani D U . . . .
C31 C 0.9417(6) 0.9356(6) 0.3245(8) 0.4395 1.0000 Uani D U . . . .
N32 N 0.8915(4) 0.7793(5) 0.3185(5) 0.2431 1.0000 Uani D U . . . .
C33 C 0.8748(4) 0.7278(5) 0.3163(7) 0.2692 1.0000 Uani D U . . . .
C34 C 0.9111(5) 0.6929(5) 0.3299(7) 0.3228 1.0000 Uani D U . . . .
C42 C 0.7662(5) 0.7967(5) 0.5533(5) 0.1336 1.0000 Uani D . . . . .
C43 C 0.7523(4) 0.8397(6) 0.5773(6) 0.1730 1.0000 Uani D . . . . .
C44 C 0.7724(5) 0.8515(5) 0.6224(6) 0.1704 1.0000 Uani D . . . . .
C45 C 0.8054(4) 0.8240(6) 0.6467(5) 0.1514 1.0000 Uani D U . . . .
C46 C 0.8175(4) 0.7794(6) 0.6239(6) 0.1607 1.0000 Uani D . . . . .
C47 C 0.7991(4) 0.7699(5) 0.5776(6) 0.1557 1.0000 Uani D . . . . .
C48 C 0.8277(4) 0.8413(5) 0.6921(5) 0.1714 1.0000 Uani D U . . . .
N49 N 0.8244(3) 0.8211(5) 0.7343(4) 0.1903 1.0000 Uani D U . . . .
C50 C 0.7906(4) 0.7823(5) 0.7358(5) 0.2177 1.0000 Uani D U . . . .
C51 C 0.7623(5) 0.7929(6) 0.7810(5) 0.3144 1.0000 Uani D U . . . .
N52 N 0.8544(3) 0.8799(4) 0.6881(4) 0.1927 1.0000 Uani D U . . . .
C53 C 0.8779(5) 0.9003(5) 0.7307(4) 0.2405 1.0000 Uani D U . . . .
C54 C 0.8904(6) 0.9546(5) 0.7180(6) 0.3767 1.0000 Uani D U . . . .
C62 C 0.7081(3) 0.8144(4) 0.4876(4) 0.1187 1.0000 Uani D . . . . .
C63 C 0.6657(4) 0.7959(4) 0.4800(4) 0.1405 1.0000 Uani D . . . . .
C64 C 0.6321(3) 0.8280(4) 0.4647(5) 0.1536 1.0000 Uani D . . . . .
C65 C 0.6390(3) 0.8792(4) 0.4598(4) 0.1417 1.0000 Uani D U . . . .
C66 C 0.6815(4) 0.8984(4) 0.4676(5) 0.1648 1.0000 Uani D . . . . .
C67 C 0.7154(3) 0.8649(4) 0.4782(4) 0.1486 1.0000 Uani D . . . . .
C68 C 0.6026(4) 0.9153(4) 0.4466(5) 0.1813 1.0000 Uani D U . . . .
N69 N 0.5825(3) 0.9099(3) 0.4029(4) 0.1950 1.0000 Uani D U . . . .
C70 C 0.5441(4) 0.9413(4) 0.3886(6) 0.2463 1.0000 Uani D U . . . .
C71 C 0.5116(4) 0.9113(5) 0.3593(7) 0.3183 1.0000 Uani D U . . . .
N72 N 0.5928(3) 0.9518(4) 0.4784(4) 0.2117 1.0000 Uani D U . . . .
C73 C 0.6102(4) 0.9551(6) 0.5298(5) 0.2389 1.0000 Uani D U . . . .
C74 C 0.5745(4) 0.9777(6) 0.5624(5) 0.2806 1.0000 Uani D U . . . .
C101 C 0.5018(3) 0.2706(4) 0.4979(5) 0.1346 1.0000 Uani D . . . . .
C102 C 0.5327(3) 0.3149(4) 0.5066(5) 0.1198 1.0000 Uani D . . . . .
C103 C 0.5352(3) 0.3590(5) 0.4797(5) 0.1393 1.0000 Uani D . . . . .
C104 C 0.5641(5) 0.3984(4) 0.4942(6) 0.1736 1.0000 Uani D . . . . .
C105 C 0.5912(4) 0.3934(5) 0.5359(5) 0.1331 1.0000 Uani D U . . . .
C106 C 0.5883(3) 0.3499(5) 0.5644(5) 0.1544 1.0000 Uani D . . . . .
C107 C 0.5585(4) 0.3120(4) 0.5499(5) 0.1458 1.0000 Uani D . . . . .
C108 C 0.6215(5) 0.4360(6) 0.5489(5) 0.2071 1.0000 Uani D U . . . .
O109 O 0.6339(4) 0.4631(4) 0.5146(5) 0.2708 1.0000 Uani D U . . . .
O110 O 0.6355(3) 0.4362(3) 0.5934(4) 0.1959 1.0000 Uani D U . . . .
C112 C 0.5247(3) 0.2208(4) 0.4920(5) 0.1323 1.0000 Uani D . . . . .
C113 C 0.5705(3) 0.2151(4) 0.4909(5) 0.1598 1.0000 Uani D . . . . .
C114 C 0.5884(4) 0.1676(4) 0.4832(6) 0.2069 1.0000 Uani D . . . . .
C115 C 0.5625(4) 0.1259(4) 0.4730(6) 0.1673 1.0000 Uani D U . . . .
C116 C 0.5171(4) 0.1302(4) 0.4750(6) 0.1925 1.0000 Uani D . . . . .
C117 C 0.5005(3) 0.1778(5) 0.4836(5) 0.1552 1.0000 Uani D . . . . .
C118 C 0.5843(4) 0.0759(5) 0.4660(8) 0.2477 1.0000 Uani D U . . . .
O119 O 0.6248(3) 0.0699(3) 0.4789(5) 0.2550 1.0000 Uani D U . . . .
O120 O 0.5585(3) 0.0425(3) 0.4502(5) 0.2626 1.0000 Uani D U . . . .
C122 C 0.4710(4) 0.2676(5) 0.5425(4) 0.1281 1.0000 Uani D . . . . .
C123 C 0.4416(5) 0.3073(4) 0.5472(4) 0.1498 1.0000 Uani D . . . . .
C124 C 0.4135(4) 0.3116(4) 0.5890(6) 0.1573 1.0000 Uani D . . . . .
C125 C 0.4167(4) 0.2762(5) 0.6279(4) 0.1367 1.0000 Uani D U . . . .
C126 C 0.4471(4) 0.2360(4) 0.6212(5) 0.1467 1.0000 Uani D . . . . .
C127 C 0.4744(4) 0.2324(4) 0.5791(6) 0.1347 1.0000 Uani D . . . . .
C128 C 0.3877(5) 0.2830(4) 0.6730(5) 0.1610 1.0000 Uani D U . . . .
O129 O 0.3705(3) 0.3249(4) 0.6837(4) 0.2049 1.0000 Uani D U . . . .
O130 O 0.3849(3) 0.2441(3) 0.7006(4) 0.1877 1.0000 Uani D U . . . .
C132 C 0.4784(3) 0.2776(4) 0.4485(5) 0.1445 1.0000 Uani D . . . . .
C133 C 0.5017(3) 0.2815(5) 0.4050(5) 0.1532 1.0000 Uani D . . . . .
C134 C 0.4830(3) 0.2865(5) 0.3580(5) 0.1801 1.0000 Uani D . . . . .
C135 C 0.4366(4) 0.2876(5) 0.3509(5) 0.1646 1.0000 Uani D U . . . .
C136 C 0.4145(3) 0.2807(5) 0.3958(5) 0.1700 1.0000 Uani D . . . . .
C137 C 0.4321(4) 0.2782(5) 0.4439(5) 0.1659 1.0000 Uani D . . . . .
C138 C 0.4148(4) 0.2912(10) 0.3003(5) 0.2653 1.0000 Uani D U . . . .
O139 O 0.4389(3) 0.2898(7) 0.2608(4) 0.3015 1.0000 Uani D U . . . .
O140 O 0.3717(3) 0.2937(6) 0.3011(4) 0.2916 1.0000 Uani D U . . . .
H31 H 0.7735 0.6992 0.4525 0.1770 1.0000 Uiso R . . . . .
H41 H 0.7618 0.6130 0.4670 0.1967 1.0000 Uiso R . . . . .
H61 H 0.6770 0.6514 0.5780 0.1992 1.0000 Uiso R . . . . .
H71 H 0.6928 0.7375 0.5654 0.2115 1.0000 Uiso R . . . . .
H101 H 0.7127 0.4853 0.5756 0.2593 1.0000 Uiso R . . . . .
H102 H 0.7446 0.4735 0.5317 0.2593 1.0000 Uiso R . . . . .
H111 H 0.7788 0.4501 0.6066 0.3563 1.0000 Uiso R . . . . .
H112 H 0.7742 0.5047 0.6259 0.3563 1.0000 Uiso R . . . . .
H113 H 0.8060 0.4929 0.5821 0.3563 1.0000 Uiso R . . . . .
H131 H 0.6347 0.6148 0.5056 0.3346 1.0000 Uiso R . . . . .
H132 H 0.6119 0.5659 0.4872 0.3346 1.0000 Uiso R . . . . .
H141 H 0.5700 0.5998 0.5517 0.3883 1.0000 Uiso R . . . . .
H142 H 0.6109 0.5968 0.5869 0.3883 1.0000 Uiso R . . . . .
H143 H 0.5881 0.5480 0.5685 0.3883 1.0000 Uiso R . . . . .
H231 H 0.8342 0.8163 0.5090 0.1911 1.0000 Uiso R . . . . .
H241 H 0.8838 0.8244 0.4425 0.1896 1.0000 Uiso R . . . . .
H261 H 0.7931 0.7850 0.3400 0.1966 1.0000 Uiso R . . . . .
H271 H 0.7446 0.7749 0.4056 0.1830 1.0000 Uiso R . . . . .
H301 H 0.9491 0.8621 0.3097 0.3339 1.0000 Uiso R . . . . .
H302 H 0.9115 0.8851 0.2774 0.3339 1.0000 Uiso R . . . . .
H311 H 0.9630 0.9462 0.3007 0.4423 1.0000 Uiso R . . . . .
H312 H 0.9548 0.9352 0.3567 0.4423 1.0000 Uiso R . . . . .
H313 H 0.9172 0.9581 0.3244 0.4423 1.0000 Uiso R . . . . .
H331 H 0.8513 0.7243 0.3397 0.2987 1.0000 Uiso R . . . . .
H332 H 0.8641 0.7202 0.2838 0.2987 1.0000 Uiso R . . . . .
H341 H 0.9007 0.6592 0.3293 0.3366 1.0000 Uiso R . . . . .
H342 H 0.9218 0.7007 0.3623 0.3366 1.0000 Uiso R . . . . .
H343 H 0.9345 0.6967 0.3065 0.3366 1.0000 Uiso R . . . . .
H431 H 0.7305 0.8607 0.5624 0.2055 1.0000 Uiso R . . . . .
H441 H 0.7623 0.8806 0.6394 0.2019 1.0000 Uiso R . . . . .
H461 H 0.8362 0.7560 0.6404 0.1920 1.0000 Uiso R . . . . .
H471 H 0.8106 0.7422 0.5594 0.1917 1.0000 Uiso R . . . . .
H501 H 0.8037 0.7499 0.7375 0.2503 1.0000 Uiso R . . . . .
H502 H 0.7726 0.7845 0.7068 0.2503 1.0000 Uiso R . . . . .
H511 H 0.7393 0.7685 0.7832 0.3297 1.0000 Uiso R . . . . .
H512 H 0.7807 0.7908 0.8097 0.3297 1.0000 Uiso R . . . . .
H513 H 0.7496 0.8255 0.7791 0.3297 1.0000 Uiso R . . . . .
H531 H 0.9035 0.8803 0.7369 0.2830 1.0000 Uiso R . . . . .
H532 H 0.8591 0.8997 0.7591 0.2830 1.0000 Uiso R . . . . .
H541 H 0.9061 0.9682 0.7456 0.4059 1.0000 Uiso R . . . . .
H542 H 0.9090 0.9548 0.6895 0.4059 1.0000 Uiso R . . . . .
H543 H 0.8647 0.9742 0.7117 0.4059 1.0000 Uiso R . . . . .
H631 H 0.6596 0.7613 0.4855 0.1717 1.0000 Uiso R . . . . .
H641 H 0.6035 0.8146 0.4576 0.1854 1.0000 Uiso R . . . . .
H661 H 0.6870 0.9334 0.4654 0.1897 1.0000 Uiso R . . . . .
H671 H 0.7450 0.8772 0.4800 0.1794 1.0000 Uiso R . . . . .
H701 H 0.5545 0.9681 0.3683 0.2791 1.0000 Uiso R . . . . .
H702 H 0.5306 0.9546 0.4178 0.2791 1.0000 Uiso R . . . . .
H711 H 0.4873 0.9320 0.3502 0.3300 1.0000 Uiso R . . . . .
H712 H 0.5252 0.8980 0.3302 0.3300 1.0000 Uiso R . . . . .
H713 H 0.5013 0.8845 0.3796 0.3300 1.0000 Uiso R . . . . .
H731 H 0.6361 0.9754 0.5306 0.2723 1.0000 Uiso R . . . . .
H732 H 0.6173 0.9223 0.5413 0.2723 1.0000 Uiso R . . . . .
H741 H 0.5850 0.9798 0.5957 0.2977 1.0000 Uiso R . . . . .
H742 H 0.5675 1.0104 0.5506 0.2977 1.0000 Uiso R . . . . .
H743 H 0.5487 0.9573 0.5613 0.2977 1.0000 Uiso R . . . . .
H1031 H 0.5173 0.3618 0.4507 0.1690 1.0000 Uiso R . . . . .
H1041 H 0.5647 0.4289 0.4759 0.2022 1.0000 Uiso R . . . . .
H1061 H 0.6067 0.3469 0.5930 0.1791 1.0000 Uiso R . . . . .
H1071 H 0.5559 0.2828 0.5700 0.1712 1.0000 Uiso R . . . . .
H1131 H 0.5888 0.2436 0.4962 0.1924 1.0000 Uiso R . . . . .
H1141 H 0.6197 0.1637 0.4838 0.2271 1.0000 Uiso R . . . . .
H1161 H 0.4986 0.1016 0.4708 0.2130 1.0000 Uiso R . . . . .
H1171 H 0.4692 0.1821 0.4819 0.1807 1.0000 Uiso R . . . . .
H1231 H 0.4398 0.3317 0.5214 0.1724 1.0000 Uiso R . . . . .
H1241 H 0.3927 0.3383 0.5919 0.1856 1.0000 Uiso R . . . . .
H1261 H 0.4488 0.2107 0.6461 0.1901 1.0000 Uiso R . . . . .
H1271 H 0.4949 0.2055 0.5755 0.1639 1.0000 Uiso R . . . . .
H1331 H 0.5332 0.2806 0.4072 0.1773 1.0000 Uiso R . . . . .
H1341 H 0.5011 0.2888 0.3291 0.2093 1.0000 Uiso R . . . . .
H1361 H 0.3832 0.2769 0.3932 0.1989 1.0000 Uiso R . . . . .
H1371 H 0.4140 0.2777 0.4729 0.1975 1.0000 Uiso R . . . . .
H91 H 0.7660 0.5622 0.5505 0.2412 1.0000 Uiso R . . . . .
H121 H 0.6633 0.5213 0.5342 0.3000 1.0000 Uiso R . . . . .
H291 H 0.8814 0.8891 0.3687 0.3042 1.0000 Uiso R . . . . .
H321 H 0.9130 0.7851 0.2983 0.2887 1.0000 Uiso R . . . . .
H491 H 0.8404 0.8296 0.7596 0.2266 1.0000 Uiso R . . . . .
H521 H 0.8583 0.8935 0.6594 0.2298 1.0000 Uiso R . . . . .
H691 H 0.5918 0.8874 0.3825 0.2326 1.0000 Uiso R . . . . .
H721 H 0.5749 0.9748 0.4684 0.2525 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.14952(8)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.529(8) yes
C1 . C22 . 1.528(8) yes
C1 . C42 . 1.533(8) yes
C1 . C62 . 1.517(8) yes
C2 . C3 . 1.387(5) yes
C2 . C7 . 1.389(5) yes
C3 . C4 . 1.387(5) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.388(5) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.387(5) yes
C5 . C8 . 1.482(8) yes
C6 . C7 . 1.394(5) yes
C6 . H61 . 0.950 no
C7 . H71 . 0.950 no
C8 . N9 . 1.314(8) yes
C8 . N12 . 1.309(8) yes
N9 . C10 . 1.458(8) yes
N9 . H91 . 0.860 no
C10 . C11 . 1.524(9) yes
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
N12 . C13 . 1.468(8) yes
N12 . H121 . 0.860 no
C13 . C14 . 1.521(9) yes
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C14 . H143 . 0.950 no
C22 . C23 . 1.398(8) yes
C22 . C27 . 1.389(8) yes
C23 . C24 . 1.399(8) yes
C23 . H231 . 0.950 no
C24 . C25 . 1.391(8) yes
C24 . H241 . 0.950 no
C25 . C26 . 1.400(8) yes
C25 . C28 . 1.503(9) yes
C26 . C27 . 1.370(8) yes
C26 . H261 . 0.950 no
C27 . H271 . 0.950 no
C28 . N29 . 1.350(9) yes
C28 . N32 . 1.353(9) yes
N29 . C30 . 1.475(8) yes
N29 . H291 . 0.860 no
C30 . C31 . 1.498(9) yes
C30 . H301 . 0.950 no
C30 . H302 . 0.950 no
C31 . H311 . 0.950 no
C31 . H312 . 0.950 no
C31 . H313 . 0.950 no
N32 . C33 . 1.462(9) yes
N32 . H321 . 0.860 no
C33 . C34 . 1.480(9) yes
C33 . H331 . 0.950 no
C33 . H332 . 0.950 no
C34 . H341 . 0.950 no
C34 . H342 . 0.950 no
C34 . H343 . 0.950 no
C42 . C43 . 1.380(8) yes
C42 . C47 . 1.386(8) yes
C43 . C44 . 1.390(8) yes
C43 . H431 . 0.950 no
C44 . C45 . 1.395(8) yes
C44 . H441 . 0.950 no
C45 . C46 . 1.386(8) yes
C45 . C48 . 1.465(9) yes
C46 . C47 . 1.383(8) yes
C46 . H461 . 0.950 no
C47 . H471 . 0.950 no
C48 . N49 . 1.260(8) yes
C48 . N52 . 1.309(8) yes
N49 . C50 . 1.451(8) yes
N49 . H491 . 0.860 no
C50 . C51 . 1.509(8) yes
C50 . H501 . 0.950 no
C50 . H502 . 0.950 no
C51 . H511 . 0.950 no
C51 . H512 . 0.950 no
C51 . H513 . 0.950 no
N52 . C53 . 1.450(8) yes
N52 . H521 . 0.860 no
C53 . C54 . 1.532(9) yes
C53 . H531 . 0.950 no
C53 . H532 . 0.950 no
C54 . H541 . 0.950 no
C54 . H542 . 0.950 no
C54 . H543 . 0.950 no
C62 . C63 . 1.381(5) yes
C62 . C67 . 1.386(5) yes
C63 . C64 . 1.387(5) yes
C63 . H631 . 0.950 no
C64 . C65 . 1.385(5) yes
C64 . H641 . 0.950 no
C65 . C66 . 1.394(5) yes
C65 . C68 . 1.500(8) yes
C66 . C67 . 1.385(5) yes
C66 . H661 . 0.950 no
C67 . H671 . 0.950 no
C68 . N69 . 1.326(8) yes
C68 . N72 . 1.327(8) yes
N69 . C70 . 1.477(8) yes
N69 . H691 . 0.860 no
C70 . C71 . 1.487(8) yes
C70 . H701 . 0.950 no
C70 . H702 . 0.950 no
C71 . H711 . 0.950 no
C71 . H712 . 0.950 no
C71 . H713 . 0.950 no
N72 . C73 . 1.478(9) yes
N72 . H721 . 0.860 no
C73 . C74 . 1.510(9) yes
C73 . H731 . 0.950 no
C73 . H732 . 0.950 no
C74 . H741 . 0.950 no
C74 . H742 . 0.950 no
C74 . H743 . 0.950 no
C101 . C102 . 1.520(8) yes
C101 . C112 . 1.503(8) yes
C101 . C122 . 1.516(8) yes
C101 . C132 . 1.512(8) yes
C102 . C103 . 1.382(8) yes
C102 . C107 . 1.400(8) yes
C103 . C104 . 1.416(8) yes
C103 . H1031 . 0.950 no
C104 . C105 . 1.393(8) yes
C104 . H1041 . 0.950 no
C105 . C106 . 1.389(8) yes
C105 . C108 . 1.496(5) yes
C106 . C107 . 1.405(8) yes
C106 . H1061 . 0.950 no
C107 . H1071 . 0.950 no
C108 . O109 . 1.227(9) yes
C108 . O110 . 1.268(8) yes
C112 . C113 . 1.385(8) yes
C112 . C117 . 1.374(8) yes
C113 . C114 . 1.391(8) yes
C113 . H1131 . 0.950 no
C114 . C115 . 1.383(8) yes
C114 . H1141 . 0.950 no
C115 . C116 . 1.373(8) yes
C115 . C118 . 1.496(5) yes
C116 . C117 . 1.382(8) yes
C116 . H1161 . 0.950 no
C117 . H1171 . 0.950 no
C118 . O119 . 1.279(8) yes
C118 . O120 . 1.256(8) yes
C122 . C123 . 1.386(8) yes
C122 . C127 . 1.362(8) yes
C123 . C124 . 1.409(8) yes
C123 . H1231 . 0.950 no
C124 . C125 . 1.410(8) yes
C124 . H1241 . 0.950 no
C125 . C126 . 1.420(8) yes
C125 . C128 . 1.504(5) yes
C126 . C127 . 1.400(8) yes
C126 . H1261 . 0.950 no
C127 . H1271 . 0.950 no
C128 . O129 . 1.263(8) yes
C128 . O130 . 1.277(8) yes
C132 . C133 . 1.368(8) yes
C132 . C137 . 1.398(8) yes
C133 . C134 . 1.387(8) yes
C133 . H1331 . 0.950 no
C134 . C135 . 1.411(8) yes
C134 . H1341 . 0.950 no
C135 . C136 . 1.390(8) yes
C135 . C138 . 1.511(5) yes
C136 . C137 . 1.395(8) yes
C136 . H1361 . 0.950 no
C137 . H1371 . 0.950 no
C138 . O139 . 1.285(8) yes
C138 . O140 . 1.300(8) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C22 . 111.6(10) yes
C2 . C1 . C42 . 105.4(10) yes
C22 . C1 . C42 . 108.0(11) yes
C2 . C1 . C62 . 112.9(9) yes
C22 . C1 . C62 . 107.1(9) yes
C42 . C1 . C62 . 111.9(10) yes
C1 . C2 . C3 . 124.1(12) yes
C1 . C2 . C7 . 117.5(12) yes
C3 . C2 . C7 . 118.2(10) yes
C2 . C3 . C4 . 124.0(11) yes
C2 . C3 . H31 . 116.1 no
C4 . C3 . H31 . 119.9 no
C3 . C4 . C5 . 116.2(11) yes
C3 . C4 . H41 . 121.3 no
C5 . C4 . H41 . 122.5 no
C4 . C5 . C6 . 121.4(10) yes
C4 . C5 . C8 . 118.8(13) yes
C6 . C5 . C8 . 119.4(13) yes
C5 . C6 . C7 . 120.6(10) yes
C5 . C6 . H61 . 117.8 no
C7 . C6 . H61 . 121.6 no
C6 . C7 . C2 . 119.3(10) yes
C6 . C7 . H71 . 119.9 no
C2 . C7 . H71 . 120.8 no
C5 . C8 . N9 . 114.1(10) yes
C5 . C8 . N12 . 121.9(10) yes
N9 . C8 . N12 . 123.9(11) yes
C8 . N9 . C10 . 124.4(9) yes
C8 . N9 . H91 . 118.0 no
C10 . N9 . H91 . 117.6 no
N9 . C10 . C11 . 107.0(7) yes
N9 . C10 . H101 . 109.4 no
C11 . C10 . H101 . 110.8 no
N9 . C10 . H102 . 110.2 no
C11 . C10 . H102 . 110.0 no
H101 . C10 . H102 . 109.5 no
C10 . C11 . H111 . 109.2 no
C10 . C11 . H112 . 109.2 no
H111 . C11 . H112 . 109.5 no
C10 . C11 . H113 . 110.0 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C8 . N12 . C13 . 124.7(11) yes
C8 . N12 . H121 . 117.5 no
C13 . N12 . H121 . 117.8 no
N12 . C13 . C14 . 106.7(8) yes
N12 . C13 . H131 . 109.8 no
C14 . C13 . H131 . 110.9 no
N12 . C13 . H132 . 110.3 no
C14 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.5 no
C13 . C14 . H141 . 108.5 no
C13 . C14 . H142 . 109.3 no
H141 . C14 . H142 . 109.5 no
C13 . C14 . H143 . 110.7 no
H141 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no
C1 . C22 . C23 . 122.4(14) yes
C1 . C22 . C27 . 120.4(12) yes
C23 . C22 . C27 . 116.9(12) yes
C22 . C23 . C24 . 114.0(12) yes
C22 . C23 . H231 . 122.8 no
C24 . C23 . H231 . 123.3 no
C23 . C24 . C25 . 129.1(12) yes
C23 . C24 . H241 . 115.9 no
C25 . C24 . H241 . 115.0 no
C24 . C25 . C26 . 115.3(12) yes
C24 . C25 . C28 . 120.3(14) yes
C26 . C25 . C28 . 123.9(14) yes
C25 . C26 . C27 . 116.1(12) yes
C25 . C26 . H261 . 121.8 no
C27 . C26 . H261 . 122.1 no
C22 . C27 . C26 . 128.3(12) yes
C22 . C27 . H271 . 114.9 no
C26 . C27 . H271 . 116.8 no
C25 . C28 . N29 . 114.1(13) yes
C25 . C28 . N32 . 111.0(13) yes
N29 . C28 . N32 . 135.0(16) yes
C28 . N29 . C30 . 116.9(14) yes
C28 . N29 . H291 . 121.6 no
C30 . N29 . H291 . 121.5 no
N29 . C30 . C31 . 107.9(8) yes
N29 . C30 . H301 . 108.6 no
C31 . C30 . H301 . 108.3 no
N29 . C30 . H302 . 110.0 no
C31 . C30 . H302 . 112.5 no
H301 . C30 . H302 . 109.5 no
C30 . C31 . H311 . 108.5 no
C30 . C31 . H312 . 112.0 no
H311 . C31 . H312 . 109.5 no
C30 . C31 . H313 . 107.9 no
H311 . C31 . H313 . 109.5 no
H312 . C31 . H313 . 109.5 no
C28 . N32 . C33 . 133.0(15) yes
C28 . N32 . H321 . 113.4 no
C33 . N32 . H321 . 113.6 no
N32 . C33 . C34 . 109.0(8) yes
N32 . C33 . H331 . 108.7 no
C34 . C33 . H331 . 108.8 no
N32 . C33 . H332 . 110.7 no
C34 . C33 . H332 . 110.1 no
H331 . C33 . H332 . 109.5 no
C33 . C34 . H341 . 110.2 no
C33 . C34 . H342 . 109.8 no
H341 . C34 . H342 . 109.5 no
C33 . C34 . H343 . 108.5 no
H341 . C34 . H343 . 109.5 no
H342 . C34 . H343 . 109.5 no
C1 . C42 . C43 . 121.2(13) yes
C1 . C42 . C47 . 123.6(13) yes
C43 . C42 . C47 . 115.1(12) yes
C42 . C43 . C44 . 117.6(12) yes
C42 . C43 . H431 . 120.1 no
C44 . C43 . H431 . 122.3 no
C43 . C44 . C45 . 126.8(12) yes
C43 . C44 . H441 . 117.7 no
C45 . C44 . H441 . 115.5 no
C44 . C45 . C46 . 115.5(12) yes
C44 . C45 . C48 . 123.4(15) yes
C46 . C45 . C48 . 121.1(15) yes
C45 . C46 . C47 . 116.7(13) yes
C45 . C46 . H461 . 120.8 no
C47 . C46 . H461 . 122.4 no
C42 . C47 . C46 . 128.0(13) yes
C42 . C47 . H471 . 114.7 no
C46 . C47 . H471 . 117.3 no
C45 . C48 . N49 . 125.3(13) yes
C45 . C48 . N52 . 117.5(12) yes
N49 . C48 . N52 . 117.2(13) yes
C48 . N49 . C50 . 112.6(13) yes
C48 . N49 . H491 . 123.5 no
C50 . N49 . H491 . 123.9 no
N49 . C50 . C51 . 106.5(8) yes
N49 . C50 . H501 . 111.0 no
C51 . C50 . H501 . 111.5 no
N49 . C50 . H502 . 109.4 no
C51 . C50 . H502 . 109.0 no
H501 . C50 . H502 . 109.5 no
C50 . C51 . H511 . 109.4 no
C50 . C51 . H512 . 108.3 no
H511 . C51 . H512 . 109.5 no
C50 . C51 . H513 . 110.8 no
H511 . C51 . H513 . 109.5 no
H512 . C51 . H513 . 109.5 no
C48 . N52 . C53 . 122.0(11) yes
C48 . N52 . H521 . 119.1 no
C53 . N52 . H521 . 119.0 no
N52 . C53 . C54 . 107.3(8) yes
N52 . C53 . H531 . 108.8 no
C54 . C53 . H531 . 111.8 no
N52 . C53 . H532 . 109.6 no
C54 . C53 . H532 . 109.8 no
H531 . C53 . H532 . 109.5 no
C53 . C54 . H541 . 108.0 no
C53 . C54 . H542 . 109.2 no
H541 . C54 . H542 . 109.5 no
C53 . C54 . H543 . 111.1 no
H541 . C54 . H543 . 109.5 no
H542 . C54 . H543 . 109.5 no
C1 . C62 . C63 . 123.4(10) yes
C1 . C62 . C67 . 118.5(9) yes
C63 . C62 . C67 . 117.9(9) yes
C62 . C63 . C64 . 119.7(9) yes
C62 . C63 . H631 . 120.2 no
C64 . C63 . H631 . 120.2 no
C63 . C64 . C65 . 121.8(9) yes
C63 . C64 . H641 . 119.2 no
C65 . C64 . H641 . 119.0 no
C64 . C65 . C66 . 118.9(10) yes
C64 . C65 . C68 . 123.0(10) yes
C66 . C65 . C68 . 118.0(10) yes
C65 . C66 . C67 . 118.1(9) yes
C65 . C66 . H661 . 120.9 no
C67 . C66 . H661 . 121.0 no
C62 . C67 . C66 . 123.0(10) yes
C62 . C67 . H671 . 118.3 no
C66 . C67 . H671 . 118.7 no
C65 . C68 . N69 . 118.2(11) yes
C65 . C68 . N72 . 118.6(11) yes
N69 . C68 . N72 . 123.2(12) yes
C68 . N69 . C70 . 121.7(11) yes
C68 . N69 . H691 . 119.3 no
C70 . N69 . H691 . 119.0 no
N69 . C70 . C71 . 110.2(7) yes
N69 . C70 . H701 . 108.5 no
C71 . C70 . H701 . 108.6 no
N69 . C70 . H702 . 109.1 no
C71 . C70 . H702 . 110.9 no
H701 . C70 . H702 . 109.5 no
C70 . C71 . H711 . 109.2 no
C70 . C71 . H712 . 110.8 no
H711 . C71 . H712 . 109.5 no
C70 . C71 . H713 . 108.4 no
H711 . C71 . H713 . 109.5 no
H712 . C71 . H713 . 109.5 no
C68 . N72 . C73 . 124.5(12) yes
C68 . N72 . H721 . 117.4 no
C73 . N72 . H721 . 118.1 no
N72 . C73 . C74 . 108.3(8) yes
N72 . C73 . H731 . 110.2 no
C74 . C73 . H731 . 110.0 no
N72 . C73 . H732 . 109.1 no
C74 . C73 . H732 . 109.8 no
H731 . C73 . H732 . 109.5 no
C73 . C74 . H741 . 109.5 no
C73 . C74 . H742 . 109.4 no
H741 . C74 . H742 . 109.5 no
C73 . C74 . H743 . 109.5 no
H741 . C74 . H743 . 109.5 no
H742 . C74 . H743 . 109.5 no
C102 . C101 . C112 . 114.9(9) yes
C102 . C101 . C122 . 107.0(10) yes
C112 . C101 . C122 . 108.5(10) yes
C102 . C101 . C132 . 108.9(9) yes
C112 . C101 . C132 . 103.3(9) yes
C122 . C101 . C132 . 114.5(10) yes
C101 . C102 . C103 . 127.9(12) yes
C101 . C102 . C107 . 115.1(12) yes
C103 . C102 . C107 . 116.7(10) yes
C102 . C103 . C104 . 121.4(11) yes
C102 . C103 . H1031 . 117.6 no
C104 . C103 . H1031 . 121.0 no
C103 . C104 . C105 . 120.6(12) yes
C103 . C104 . H1041 . 120.4 no
C105 . C104 . H1041 . 119.0 no
C104 . C105 . C106 . 119.0(12) yes
C104 . C105 . C108 . 118.1(13) yes
C106 . C105 . C108 . 122.9(14) yes
C105 . C106 . C107 . 119.2(11) yes
C105 . C106 . H1061 . 118.5 no
C107 . C106 . H1061 . 122.3 no
C106 . C107 . C102 . 123.0(10) yes
C106 . C107 . H1071 . 119.0 no
C102 . C107 . H1071 . 118.0 no
C105 . C108 . O109 . 117.2(12) yes
C105 . C108 . O110 . 115.1(12) yes
O109 . C108 . O110 . 127.1(13) yes
C101 . C112 . C113 . 123.6(10) yes
C101 . C112 . C117 . 120.6(9) yes
C113 . C112 . C117 . 115.6(9) yes
C112 . C113 . C114 . 119.1(9) yes
C112 . C113 . H1131 . 119.2 no
C114 . C113 . H1131 . 121.6 no
C113 . C114 . C115 . 122.9(10) yes
C113 . C114 . H1141 . 118.9 no
C115 . C114 . H1141 . 118.2 no
C114 . C115 . C116 . 119.0(10) yes
C114 . C115 . C118 . 119.6(11) yes
C116 . C115 . C118 . 121.0(11) yes
C115 . C116 . C117 . 116.3(10) yes
C115 . C116 . H1161 . 120.8 no
C117 . C116 . H1161 . 123.0 no
C116 . C117 . C112 . 126.9(10) yes
C116 . C117 . H1171 . 117.4 no
C112 . C117 . H1171 . 115.7 no
C115 . C118 . O119 . 119.7(10) yes
C115 . C118 . O120 . 113.8(10) yes
O119 . C118 . O120 . 126.4(11) yes
C101 . C122 . C123 . 115.0(12) yes
C101 . C122 . C127 . 124.1(12) yes
C123 . C122 . C127 . 120.5(6) yes
C122 . C123 . C124 . 121.2(6) yes
C122 . C123 . H1231 . 119.4 no
C124 . C123 . H1231 . 119.4 no
C123 . C124 . C125 . 119.6(6) yes
C123 . C124 . H1241 . 121.3 no
C125 . C124 . H1241 . 119.0 no
C124 . C125 . C126 . 117.0(6) yes
C124 . C125 . C128 . 118.4(12) yes
C126 . C125 . C128 . 124.5(13) yes
C125 . C126 . C127 . 122.2(6) yes
C125 . C126 . H1261 . 118.6 no
C127 . C126 . H1261 . 119.2 no
C126 . C127 . C122 . 119.4(6) yes
C126 . C127 . H1271 . 121.0 no
C122 . C127 . H1271 . 119.6 no
C125 . C128 . O129 . 121.8(11) yes
C125 . C128 . O130 . 114.0(11) yes
O129 . C128 . O130 . 124.0(11) yes
C101 . C132 . C133 . 121.3(10) yes
C101 . C132 . C137 . 123.0(12) yes
C133 . C132 . C137 . 115.7(11) yes
C132 . C133 . C134 . 125.2(11) yes
C132 . C133 . H1331 . 117.1 no
C134 . C133 . H1331 . 117.7 no
C133 . C134 . C135 . 121.8(11) yes
C133 . C134 . H1341 . 121.1 no
C135 . C134 . H1341 . 117.1 no
C134 . C135 . C136 . 110.6(11) yes
C134 . C135 . C138 . 123.6(12) yes
C136 . C135 . C138 . 125.6(11) yes
C135 . C136 . C137 . 128.9(11) yes
C135 . C136 . H1361 . 115.0 no
C137 . C136 . H1361 . 116.1 no
C132 . C137 . C136 . 117.4(11) yes
C132 . C137 . H1371 . 119.7 no
C136 . C137 . H1371 . 122.9 no
C135 . C138 . O139 . 119.7(11) yes
C135 . C138 . O140 . 114.9(11) yes
O139 . C138 . O140 . 125.4(13) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . C27 . 126 0.95 2.52 3.172(18) yes
C13 . H131 . C6 . 121 0.95 2.57 3.171(18) yes
C33 . H331 . C26 . 128 0.95 2.47 3.145(18) yes
C43 . H431 . C67 . 125 0.95 2.31 2.959(18) yes
C137 . H1371 . C123 . 120 0.95 2.30 2.896(18) yes
N12 . H121 . O109 . 145 0.86 1.86 2.611(18) yes
N32 . H321 . O139 4_555 155 0.86 1.77 2.578(18) yes
N49 . H491 . O129 4_556 160 0.86 1.78 2.603(18) yes
N52 . H521 . O110 6_655 172 0.86 2.11 2.966(18) yes
N72 . H721 . O120 1_565 155 0.86 1.93 2.735(18) yes




# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 2 0 x .
0 4 1 x .
3 7 1 x .
6 2 0 x .
# end of ARCHIVE-HKL.CIF 
# looking for PLATON_SQD.SQF 

# SQUEEZE RESULTS (Version = 210723) 
# Note: Data are Listed for all Voids in the P1 Unit Cell 
# i.e. Centre of Gravity, Solvent Accessible Volume, 
# Recovered number of Electrons in the Void and 
# Details about the Squeezed Material 
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.008 0.000 0.000 10380 1852 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
# end of PLATON_SQD.SQF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_Tetra_BPDC
_database_code_depnum_ccdc_archive 'CCDC 2503997'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2025-11-19 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT601_Tetra_BPDC          
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS   <=         32 Ang**3
RESPONSE: This small void appears to be genuine and results from inefficient
packing. The max/min electron density are 0.29/-0.19 so it does not appear
that any solvent molecules have been missed.
;

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
The asymmetric unit contains one quarter of a tetra-amidinium molecule
and one dicarboxylate molecule, which has been spontaneously mono-protonated.
The structure is close-packed. 

One of the ethyl groups is disordered. This was modelled over two positions
(occupancies = 0.5:0.5). It was necessary to add restraints to the C-N and C-C
bond lengths and N-C-C angles of the disordered ethyl groups to achieve a 
sensible refinement.

Amidinium N-H groups and the carboxylic acid hydrogen atom were clearly visible
in the difference map and their positions were refined with restraints. C-H 
positions were initially refined with restraints and then these positions were
used as the basis for a riding model.
;

_cell_length_a                   22.70732(9)
_cell_length_b                   22.70732(9)
_cell_length_c                   17.56650(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9057.68(9)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a '
_symmetry_space_group_name_Hall  '-I 4ad'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
y+3/4,-x+3/4,z+3/4
-y+3/4,x+3/4,-z+3/4
y+5/4,-x+5/4,z+5/4
-y+5/4,x+5/4,-z+5/4
x+1/2,y,-z+1/2
-x+1/2,-y,z+1/2
x+1,y+1/2,-z+1
-x+1,-y+1/2,z+1
-y+3/4,x+1/4,z+1/4
y+3/4,-x+1/4,-z+1/4
-y+5/4,x+3/4,z+3/4
y+5/4,-x+3/4,-z+3/4

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C101 H100 N8 O16'
_chemical_formula_moiety         'C45 H64 N8, 4(C14 H9 O4)'
_chemical_compound_source        synthesized
_chemical_formula_weight         1681.96

_cell_measurement_reflns_used    40910
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      77.5
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_max          0.46

_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             3560
_exptl_absorpt_coefficient_mu    0.680

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            67557
_diffrn_reflns_av_unetI/netI     1.574
_reflns_number_total             4625
_diffrn_reflns_av_R_equivalents  0.0375

_diffrn_reflns_theta_min         3.181
_diffrn_reflns_theta_max         74.412
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        74.412
_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -19
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   2.97
_oxford_diffrn_Wilson_scale      0.54

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.19
_refine_diff_density_max         0.29

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     15
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4625
_refine_ls_R_factor_ref          0.0449
_refine_ls_wR_factor_ref         0.1287
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_shift/su_max          0.0006320
_refine_ls_shift/su_mean         0.0000874

# Computed with I/sigma = -10 
_reflns_number_all               4625
_refine_ls_R_factor_all          0.0449
_refine_ls_wR_factor_all         0.1287

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4222
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_gt          0.1253


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 5.01P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.5000 0.7500 0.1250 0.0302 1.0000 Uani S T . . . .
C2 C 0.54860(6) 0.76962(6) 0.06905(6) 0.0318 1.0000 Uani . . . . . .
C3 C 0.54154(6) 0.82283(6) 0.03024(7) 0.0371 1.0000 Uani . . . . . .
C4 C 0.57635(7) 0.83647(6) -0.03187(7) 0.0404 1.0000 Uani . . . . . .
C5 C 0.61983(6) 0.79747(6) -0.05619(7) 0.0386 1.0000 Uani . . . . . .
C6 C 0.62953(7) 0.74590(6) -0.01580(7) 0.0408 1.0000 Uani . . . . . .
C7 C 0.59373(6) 0.73197(6) 0.04629(7) 0.0377 1.0000 Uani . . . . . .
C8 C 0.65438(7) 0.81026(6) -0.12639(7) 0.0390 1.0000 Uani D . . . . .
N9 N 0.71180(5) 0.81236(5) -0.12111(6) 0.0378 1.0000 Uani D . . . . .
C10 C 0.75058(6) 0.82213(6) -0.18667(7) 0.0387 1.0000 Uani D . . . . .
C11 C 0.81234(7) 0.80191(7) -0.16917(9) 0.0455 1.0000 Uani . . . . . .
N12 N 0.62697(6) 0.81833(6) -0.19187(6) 0.0471 1.0000 Uani D . . . . .
C13 C 0.56857(19) 0.79417(16) -0.2081(2) 0.0393 0.5000 Uani D . . . 1 .
C14 C 0.52819(17) 0.84707(16) -0.2246(2) 0.0569 0.5000 Uani D . . . 1 .
C23 C 0.56086(19) 0.8222(3) -0.2077(2) 0.0562 0.5000 Uani D . . . 2 .
C24 C 0.54855(19) 0.7969(2) -0.2848(2) 0.0724 0.5000 Uani D . . . 2 .
O51 O 0.82673(5) 0.65472(5) -0.16281(5) 0.0498 1.0000 Uani . . . . . .
O52 O 0.81633(4) 0.55793(4) -0.15014(5) 0.0386 1.0000 Uani D . . . . .
C53 C 0.81429(6) 0.61117(6) -0.12495(7) 0.0355 1.0000 Uani . . . . . .
C54 C 0.79701(6) 0.61708(6) -0.04287(7) 0.0358 1.0000 Uani . . . . . .
C55 C 0.79365(8) 0.67223(6) -0.00917(7) 0.0459 1.0000 Uani . . . . . .
C56 C 0.78045(8) 0.67787(6) 0.06778(7) 0.0480 1.0000 Uani . . . . . .
C57 C 0.77074(6) 0.62817(6) 0.11257(7) 0.0371 1.0000 Uani . . . . . .
C58 C 0.77305(6) 0.57310(6) 0.07783(7) 0.0374 1.0000 Uani . . . . . .
C59 C 0.78580(6) 0.56743(6) 0.00092(7) 0.0365 1.0000 Uani . . . . . .
C60 C 0.75845(6) 0.63225(6) 0.19569(7) 0.0360 1.0000 Uani . . . . . .
C61 C 0.78309(8) 0.67602(6) 0.24101(8) 0.0476 1.0000 Uani . . . . . .
C62 C 0.77324(7) 0.67719(6) 0.31921(7) 0.0439 1.0000 Uani . . . . . .
C63 C 0.73833(6) 0.63433(6) 0.35345(6) 0.0329 1.0000 Uani . . . . . .
C64 C 0.71347(6) 0.59075(6) 0.30854(7) 0.0362 1.0000 Uani . . . . . .
C65 C 0.72286(6) 0.59019(6) 0.23050(7) 0.0372 1.0000 Uani . . . . . .
C66 C 0.72816(6) 0.63500(6) 0.43829(6) 0.0331 1.0000 Uani . . . . . .
O67 O 0.74432(5) 0.67783(5) 0.47571(5) 0.0456 1.0000 Uani . . . . . .
O68 O 0.70249(5) 0.58918(4) 0.46442(5) 0.0427 1.0000 Uani . . . . . .
H31 H 0.5096 0.8488 0.0428 0.0482 1.0000 Uiso R . . . . .
H41 H 0.5706 0.8726 -0.0610 0.0492 1.0000 Uiso R . . . . .
H61 H 0.6600 0.7175 -0.0349 0.0488 1.0000 Uiso R . . . . .
H71 H 0.6000 0.6958 0.0712 0.0489 1.0000 Uiso R . . . . .
H101 H 0.7532 0.8617 -0.1954 0.0466 1.0000 Uiso R . . . . .
H102 H 0.7346 0.8013 -0.2313 0.0473 1.0000 Uiso R . . . . .
H111 H 0.8365 0.8106 -0.2174 0.0669 1.0000 Uiso R . . . . .
H112 H 0.8280 0.8226 -0.1237 0.0653 1.0000 Uiso R . . . . .
H113 H 0.8141 0.7593 -0.1617 0.0659 1.0000 Uiso R . . . . .
H132 H 0.5685 0.7663 -0.2446 0.0475 0.5000 Uiso R . . . 1 .
H131 H 0.5553 0.7709 -0.1629 0.0470 0.5000 Uiso R . . . 1 .
H141 H 0.4921 0.8361 -0.2464 0.0853 0.5000 Uiso R . . . 1 .
H142 H 0.5489 0.8764 -0.2507 0.0870 0.5000 Uiso R . . . 1 .
H143 H 0.5182 0.8647 -0.1742 0.0862 0.5000 Uiso R . . . 1 .
H232 H 0.5490 0.8637 -0.2028 0.0706 0.5000 Uiso R . . . 2 .
H231 H 0.5370 0.7985 -0.1686 0.0702 0.5000 Uiso R . . . 2 .
H241 H 0.5051 0.7993 -0.2806 0.1049 0.5000 Uiso R . . . 2 .
H243 H 0.5670 0.8239 -0.3201 0.1035 0.5000 Uiso R . . . 2 .
H242 H 0.5652 0.7573 -0.2762 0.1042 0.5000 Uiso R . . . 2 .
H551 H 0.8001 0.7059 -0.0384 0.0560 1.0000 Uiso R . . . . .
H561 H 0.7798 0.7162 0.0895 0.0606 1.0000 Uiso R . . . . .
H581 H 0.7674 0.5396 0.1080 0.0476 1.0000 Uiso R . . . . .
H591 H 0.7884 0.5276 -0.0229 0.0454 1.0000 Uiso R . . . . .
H611 H 0.8080 0.7034 0.2166 0.0573 1.0000 Uiso R . . . . .
H621 H 0.7891 0.7068 0.3472 0.0542 1.0000 Uiso R . . . . .
H641 H 0.6903 0.5615 0.3320 0.0443 1.0000 Uiso R . . . . .
H651 H 0.7067 0.5602 0.1997 0.0477 1.0000 Uiso R . . . . .
H91 H 0.7270(6) 0.8151(7) -0.0758(8) 0.0467(18) 1.0000 Uiso D . . . . .
H121 H 0.6474(7) 0.8308(8) -0.2318(9) 0.0568(19) 1.0000 Uiso D . . . . .
H521 H 0.8264(8) 0.5556(9) -0.2014(9) 0.0595(19) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.340(8)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 8_544 1.5435(12) yes
C1 . C2 14_465 1.5435(12) yes
C1 . C2 12_564 1.5435(12) yes
C1 . C2 . 1.5435(12) yes
C2 . C3 . 1.3965(18) yes
C2 . C7 . 1.3931(19) yes
C3 . C4 . 1.3823(18) yes
C3 . H31 . 0.960 no
C4 . C5 . 1.394(2) yes
C4 . H41 . 0.976 no
C5 . C6 . 1.387(2) yes
C5 . C8 . 1.4901(16) yes
C6 . C7 . 1.3966(17) yes
C6 . H61 . 1.003 no
C7 . H71 . 0.941 no
C8 . N9 . 1.3081(19) yes
C8 . N12 . 1.3206(18) yes
N9 . C10 . 1.4667(16) yes
N9 . H91 . 0.870(14) no
C10 . C11 . 1.507(2) yes
C10 . H101 . 0.914 no
C10 . H102 . 0.984 no
C11 . H111 . 1.028 no
C11 . H112 . 0.993 no
C11 . H113 . 0.977 no
N12 . H121 . 0.886(14) no
C13 . C14 . 1.539(4) yes
C13 . H132 . 0.900 no
C13 . H131 . 1.000 no
C14 . H141 . 0.939 no
C14 . H142 . 0.936 no
C14 . H143 . 0.997 no
C23 . C24 . 1.498(5) yes
C23 . H232 . 0.984 no
C23 . H231 . 1.027 no
C24 . H241 . 0.990 no
C24 . H243 . 0.968 no
C24 . H242 . 0.987 no
O51 . C53 . 1.2247(17) yes
O52 . C53 . 1.2883(16) yes
O52 . H521 . 0.930(15) no
C53 . C54 . 1.5002(16) yes
C54 . C55 . 1.3874(19) yes
C54 . C59 . 1.3885(19) yes
C55 . C56 . 1.3905(17) yes
C55 . H551 . 0.931 no
C56 . C57 . 1.3932(19) yes
C56 . H561 . 0.950 no
C57 . C58 . 1.3924(19) yes
C57 . C60 . 1.4895(16) yes
C58 . C59 . 1.3876(17) yes
C58 . H581 . 0.935 no
C59 . H591 . 0.999 no
C60 . C61 . 1.391(2) yes
C60 . C65 . 1.3927(19) yes
C61 . C62 . 1.3921(18) yes
C61 . H611 . 0.944 no
C62 . C63 . 1.3918(19) yes
C62 . H621 . 0.908 no
C63 . C64 . 1.3857(18) yes
C63 . C66 . 1.5083(15) yes
C64 . C65 . 1.3873(17) yes
C64 . H641 . 0.943 no
C65 . H651 . 0.944 no
C66 . O67 . 1.2300(16) yes
C66 . O68 . 1.2779(16) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 8_544 C1 . C2 14_465 100.90(9) yes
C2 8_544 C1 . C2 12_564 113.92(5) yes
C2 14_465 C1 . C2 12_564 113.92(5) yes
C2 8_544 C1 . C2 . 113.92(5) yes
C2 14_465 C1 . C2 . 113.92(5) yes
C2 12_564 C1 . C2 . 100.90(9) yes
C1 . C2 . C3 . 118.59(10) yes
C1 . C2 . C7 . 122.10(10) yes
C3 . C2 . C7 . 118.38(11) yes
C2 . C3 . C4 . 120.90(13) yes
C2 . C3 . H31 . 120.3 no
C4 . C3 . H31 . 118.4 no
C3 . C4 . C5 . 120.31(13) yes
C3 . C4 . H41 . 121.7 no
C5 . C4 . H41 . 117.9 no
C4 . C5 . C6 . 119.50(12) yes
C4 . C5 . C8 . 120.19(12) yes
C6 . C5 . C8 . 120.29(13) yes
C5 . C6 . C7 . 119.88(13) yes
C5 . C6 . H61 . 118.8 no
C7 . C6 . H61 . 121.1 no
C6 . C7 . C2 . 120.89(12) yes
C6 . C7 . H71 . 118.2 no
C2 . C7 . H71 . 120.9 no
C5 . C8 . N9 . 118.24(12) yes
C5 . C8 . N12 . 119.98(13) yes
N9 . C8 . N12 . 121.77(12) yes
C8 . N9 . C10 . 123.25(11) yes
C8 . N9 . H91 . 117.5(9) no
C10 . N9 . H91 . 118.1(9) no
N9 . C10 . C11 . 110.63(11) yes
N9 . C10 . H101 . 108.7 no
C11 . C10 . H101 . 105.8 no
N9 . C10 . H102 . 109.3 no
C11 . C10 . H102 . 111.1 no
H101 . C10 . H102 . 111.2 no
C10 . C11 . H111 . 105.7 no
C10 . C11 . H112 . 110.7 no
H111 . C11 . H112 . 112.4 no
C10 . C11 . H113 . 111.5 no
H111 . C11 . H113 . 106.1 no
H112 . C11 . H113 . 110.2 no
C8 . N12 . H121 . 119.1(11) no
N12 . C13 . C14 . 106.5(3) yes
N12 . C13 . H132 . 113.8 no
C14 . C13 . H132 . 114.5 no
N12 . C13 . H131 . 108.5 no
C14 . C13 . H131 . 112.4 no
H132 . C13 . H131 . 101.1 no
C13 . C14 . H141 . 113.0 no
C13 . C14 . H142 . 110.4 no
H141 . C14 . H142 . 115.2 no
C13 . C14 . H143 . 106.3 no
H141 . C14 . H143 . 105.7 no
H142 . C14 . H143 . 105.3 no
N12 . C23 . C24 . 109.0(3) yes
N12 . C23 . H232 . 107.9 no
C24 . C23 . H232 . 113.2 no
N12 . C23 . H231 . 111.5 no
C24 . C23 . H231 . 107.8 no
H232 . C23 . H231 . 107.5 no
C23 . C24 . H241 . 95.5 no
C23 . C24 . H243 . 104.8 no
H241 . C24 . H243 . 116.4 no
C23 . C24 . H242 . 98.0 no
H241 . C24 . H242 . 114.8 no
H243 . C24 . H242 . 120.7 no
C53 . O52 . H521 . 113.2(12) no
O52 . C53 . O51 . 124.25(11) yes
O52 . C53 . C54 . 115.05(11) yes
O51 . C53 . C54 . 120.67(12) yes
C53 . C54 . C55 . 120.35(12) yes
C53 . C54 . C59 . 120.52(12) yes
C55 . C54 . C59 . 119.11(11) yes
C54 . C55 . C56 . 120.65(13) yes
C54 . C55 . H551 . 119.8 no
C56 . C55 . H551 . 119.6 no
C55 . C56 . C57 . 120.56(13) yes
C55 . C56 . H561 . 118.5 no
C57 . C56 . H561 . 120.9 no
C56 . C57 . C58 . 118.30(11) yes
C56 . C57 . C60 . 122.20(12) yes
C58 . C57 . C60 . 119.50(11) yes
C57 . C58 . C59 . 121.19(12) yes
C57 . C58 . H581 . 118.4 no
C59 . C58 . H581 . 120.3 no
C54 . C59 . C58 . 120.15(12) yes
C54 . C59 . H591 . 119.5 no
C58 . C59 . H591 . 120.3 no
C57 . C60 . C61 . 122.02(12) yes
C57 . C60 . C65 . 119.77(12) yes
C61 . C60 . C65 . 118.18(11) yes
C60 . C61 . C62 . 120.92(13) yes
C60 . C61 . H611 . 116.9 no
C62 . C61 . H611 . 122.1 no
C61 . C62 . C63 . 120.30(13) yes
C61 . C62 . H621 . 119.0 no
C63 . C62 . H621 . 120.7 no
C62 . C63 . C64 . 119.03(11) yes
C62 . C63 . C66 . 120.48(11) yes
C64 . C63 . C66 . 120.48(11) yes
C63 . C64 . C65 . 120.43(12) yes
C63 . C64 . H641 . 118.9 no
C65 . C64 . H641 . 120.7 no
C60 . C65 . C64 . 121.11(12) yes
C60 . C65 . H651 . 117.9 no
C64 . C65 . H651 . 120.9 no
C63 . C66 . O67 . 119.36(11) yes
C63 . C66 . O68 . 114.62(11) yes
O67 . C66 . O68 . 126.02(11) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C10 . H102 . O51 4_664 127 0.98 2.53 3.217(2) yes
C11 . H112 . O52 16_464 122 0.99 2.60 3.232(2) yes
C11 . H113 . O51 . 171 0.98 2.39 3.360(2) yes
C24 . H243 . O51 4_664 129 0.97 2.48 3.174(2) yes
C58 . H581 . O52 7_454 133 0.94 2.58 3.287(2) yes
N9 . H91 . O67 4_665 176.9(14) 0.870(14) 1.882(14) 2.751(2) yes
N12 . H121 . O51 4_664 162.2(16) 0.886(14) 1.971(15) 2.828(2) yes
O52 . H521 . C66 7_453 155.3(17) 0.930(15) 2.472(16) 3.340(2) yes
O52 . H521 . O68 7_453 175.1(19) 0.930(15) 1.518(15) 2.447(2) yes


# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
