# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_P480
_database_code_depnum_ccdc_archive 'CCDC 2222212'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Br2 O3'
_chemical_formula_sum            'C26 H18 Br2 O3'
_chemical_formula_weight         538.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   37.4948(7)
_cell_length_b                   5.55660(10)
_cell_length_c                   27.3597(5)
_cell_angle_alpha                90
_cell_angle_beta                 130.3290(10)
_cell_angle_gamma                90
_cell_volume                     4345.51(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9828
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      30.24
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    3.757
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5443
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31

_diffrn_reflns_number            101028
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.175
_diffrn_reflns_theta_max         33.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8288
_reflns_number_gt                5602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²+9.9543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8288
_refine_ls_number_parameters     289
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54214(2) 1.01383(5) 0.33882(2) 0.03542(7) Uani 1 1 d . . . . .
Br2 Br 0.50502(2) -0.35886(7) 0.57377(2) 0.05202(9) Uani 1 1 d . . . . .
O1 O 0.78413(6) -0.5044(3) 0.69962(8) 0.0321(3) Uani 1 1 d . . . . .
O2 O 0.81094(5) 0.2786(3) 0.61364(8) 0.0311(3) Uani 1 1 d . . . . .
O3A O 0.73723(8) -0.1449(5) 0.72402(10) 0.0309(5) Uani 0.687(3) 1 d D . P A 1
H3A H 0.739395 -0.046557 0.749146 0.046 Uiso 0.687(3) 1 calc R U P A 1
C20A C 0.69813(13) -0.0833(12) 0.6596(3) 0.0252(6) Uani 0.687(3) 1 d D . P A 1
H20A H 0.698566 0.093598 0.653213 0.030 Uiso 0.687(3) 1 calc R U P A 1
O3B O 0.70273(17) 0.1529(10) 0.6655(2) 0.0309(5) Uani 0.313(3) 1 d D . P A 2
H3B H 0.720817 0.199625 0.703773 0.046 Uiso 0.313(3) 1 calc R U P A 2
C20B C 0.7001(2) -0.103(2) 0.6637(5) 0.0252(6) Uani 0.313(3) 1 d D . P A 2
H20B H 0.724250 -0.169450 0.707872 0.030 Uiso 0.313(3) 1 calc R U P A 2
C1 C 0.87566(8) -0.4096(4) 0.74953(11) 0.0303(5) Uani 1 1 d . . . . .
H1 H 0.870919 -0.551207 0.764134 0.036 Uiso 1 1 calc R U . . .
C2 C 0.91991(8) -0.3512(4) 0.77233(11) 0.0330(5) Uani 1 1 d . . . . .
H2 H 0.945614 -0.452939 0.802714 0.040 Uiso 1 1 calc R U . . .
C3 C 0.92705(8) -0.1440(4) 0.75103(11) 0.0328(5) Uani 1 1 d . . . . .
H3 H 0.957612 -0.104389 0.767140 0.039 Uiso 1 1 calc R U . . .
C4 C 0.88968(7) 0.0045(4) 0.70638(10) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.894563 0.145362 0.691695 0.034 Uiso 1 1 calc R U . . .
C5 C 0.84471(7) -0.0538(4) 0.68301(10) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.83796(7) -0.2599(4) 0.70502(10) 0.0250(4) Uani 1 1 d . . . . .
C7 C 0.79053(7) -0.3206(4) 0.68123(10) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.75082(7) -0.1563(4) 0.63453(10) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.75674(7) 0.0403(4) 0.61042(10) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.80457(7) 0.1020(4) 0.63380(10) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.71705(7) 0.1958(4) 0.56312(10) 0.0254(4) Uani 1 1 d . . . . .
H11 H 0.689547 0.167659 0.557367 0.031 Uiso 1 1 calc R U . . .
C12 C 0.71355(7) 0.3703(4) 0.52694(10) 0.0242(4) Uani 1 1 d . . . . .
H12 H 0.740218 0.402734 0.530953 0.029 Uiso 1 1 calc R U . . .
C13 C 0.67152(7) 0.5166(4) 0.48125(9) 0.0229(4) Uani 1 1 d . . . . .
C14 C 0.67502(7) 0.7222(4) 0.45555(10) 0.0247(4) Uani 1 1 d . . . . .
H14 H 0.704207 0.760045 0.466721 0.030 Uiso 1 1 calc R U . . .
C15 C 0.63717(7) 0.8737(4) 0.41410(10) 0.0259(4) Uani 1 1 d . . . . .
H15 H 0.640361 1.014385 0.397491 0.031 Uiso 1 1 calc R U . . .
C16 C 0.59485(7) 0.8152(4) 0.39757(10) 0.0253(4) Uani 1 1 d . . . . .
C17 C 0.58960(7) 0.6103(5) 0.42131(11) 0.0318(5) Uani 1 1 d . . . . .
H17 H 0.560080 0.571807 0.409056 0.038 Uiso 1 1 calc R U . . .
C18 C 0.62774(7) 0.4628(4) 0.46297(11) 0.0308(5) Uani 1 1 d . . . . .
H18 H 0.624318 0.322719 0.479517 0.037 Uiso 1 1 calc R U . . .
C19 C 0.70503(7) -0.2212(4) 0.61773(10) 0.0235(4) Uani 1 1 d D . . . .
H19A H 0.704350 -0.396317 0.623765 0.028 Uiso 1 1 calc R U . A 1
H19B H 0.679011 -0.183308 0.572041 0.028 Uiso 1 1 calc R U . A 1
C21 C 0.65166(7) -0.1513(4) 0.64115(10) 0.0260(4) Uani 1 1 d D . . . .
C22 C 0.61327(8) -0.0047(5) 0.59937(12) 0.0346(5) Uani 1 1 d . . . . .
H22 H 0.616898 0.139020 0.584155 0.041 Uiso 1 1 calc R U . . .
C23 C 0.56945(8) -0.0632(5) 0.57917(12) 0.0394(6) Uani 1 1 d . . . . .
H23 H 0.543397 0.039827 0.550902 0.047 Uiso 1 1 calc R U . . .
C24 C 0.56462(8) -0.2740(5) 0.60101(11) 0.0335(5) Uani 1 1 d . . . . .
C25 C 0.60238(9) -0.4226(5) 0.64313(12) 0.0352(5) Uani 1 1 d . . . . .
H25 H 0.598623 -0.566098 0.658256 0.042 Uiso 1 1 calc R U . . .
C26 C 0.64600(8) -0.3602(5) 0.66321(12) 0.0329(5) Uani 1 1 d . . . . .
H26 H 0.672153 -0.461555 0.692314 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.896(2) . ?
Br2 C24 1.902(2) . ?
O1 C7 1.228(3) . ?
O2 C10 1.223(3) . ?
O3A C20A 1.425(7) . ?
O3A H3A 0.8400 . ?
C20A C21 1.515(3) . ?
C20A C19 1.533(3) . ?
C20A H20A 1.0000 . ?
O3B C20B 1.425(9) . ?
O3B H3B 0.8400 . ?
C20B C21 1.515(4) . ?
C20B C19 1.533(4) . ?
C20B H20B 1.0000 . ?
C1 C2 1.381(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 C10 1.485(3) . ?
C6 C7 1.484(3) . ?
C7 C8 1.490(3) . ?
C8 C9 1.367(3) . ?
C8 C19 1.506(3) . ?
C9 C11 1.464(3) . ?
C9 C10 1.503(3) . ?
C11 C12 1.330(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.469(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 C18 1.404(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C22 1.383(3) . ?
C21 C26 1.387(3) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C25 C26 1.391(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20A O3A H3A 109.5 . . ?
O3A C20A C21 113.1(4) . . ?
O3A C20A C19 105.6(4) . . ?
C21 C20A C19 109.92(19) . . ?
O3A C20A H20A 109.4 . . ?
C21 C20A H20A 109.4 . . ?
C19 C20A H20A 109.4 . . ?
C20B O3B H3B 109.5 . . ?
O3B C20B C21 103.2(6) . . ?
O3B C20B C19 114.3(8) . . ?
C21 C20B C19 109.9(3) . . ?
O3B C20B H20B 109.7 . . ?
C21 C20B H20B 109.7 . . ?
C19 C20B H20B 109.7 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 C10 120.72(19) . . ?
C4 C5 C10 119.6(2) . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 C7 119.96(19) . . ?
C1 C6 C7 119.8(2) . . ?
O1 C7 C6 120.4(2) . . ?
O1 C7 C8 120.59(19) . . ?
C6 C7 C8 119.04(19) . . ?
C9 C8 C7 121.31(18) . . ?
C9 C8 C19 123.58(18) . . ?
C7 C8 C19 115.09(18) . . ?
C8 C9 C11 120.59(18) . . ?
C8 C9 C10 119.92(18) . . ?
C11 C9 C10 119.47(18) . . ?
O2 C10 C5 119.85(18) . . ?
O2 C10 C9 121.27(19) . . ?
C5 C10 C9 118.88(19) . . ?
C12 C11 C9 129.98(19) . . ?
C12 C11 H11 115.0 . . ?
C9 C11 H11 115.0 . . ?
C11 C12 C13 124.88(19) . . ?
C11 C12 H12 117.6 . . ?
C13 C12 H12 117.6 . . ?
C14 C13 C18 117.75(19) . . ?
C14 C13 C12 118.99(18) . . ?
C18 C13 C12 123.2(2) . . ?
C15 C14 C13 122.01(19) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 Br1 119.22(17) . . ?
C17 C16 Br1 119.26(15) . . ?
C18 C17 C16 119.25(19) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C13 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C8 C19 C20A 111.27(18) . . ?
C8 C19 C20B 111.54(19) . . ?
C8 C19 H19A 109.4 . . ?
C20A C19 H19A 109.4 . . ?
C8 C19 H19B 109.4 . . ?
C20A C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C22 C21 C26 118.8(2) . . ?
C22 C21 C20A 119.1(4) . . ?
C26 C21 C20A 122.1(4) . . ?
C22 C21 C20B 124.4(6) . . ?
C26 C21 C20B 116.8(6) . . ?
C21 C22 C23 121.4(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 118.6(2) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 121.3(2) . . ?
C23 C24 Br2 119.44(18) . . ?
C25 C24 Br2 119.29(19) . . ?
C24 C25 C26 119.3(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C21 C26 C25 120.6(2) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C5 C10 -178.3(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C10 C5 C6 C1 177.69(19) . . . . ?
C4 C5 C6 C7 179.02(19) . . . . ?
C10 C5 C6 C7 -2.5(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -179.1(2) . . . . ?
C5 C6 C7 O1 178.8(2) . . . . ?
C1 C6 C7 O1 -1.4(3) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C1 C6 C7 C8 178.96(19) . . . . ?
O1 C7 C8 C9 -175.7(2) . . . . ?
C6 C7 C8 C9 4.0(3) . . . . ?
O1 C7 C8 C19 5.5(3) . . . . ?
C6 C7 C8 C19 -174.80(18) . . . . ?
C7 C8 C9 C11 178.16(19) . . . . ?
C19 C8 C9 C11 -3.2(3) . . . . ?
C7 C8 C9 C10 -3.5(3) . . . . ?
C19 C8 C9 C10 175.20(18) . . . . ?
C6 C5 C10 O2 -177.9(2) . . . . ?
C4 C5 C10 O2 0.6(3) . . . . ?
C6 C5 C10 C9 3.0(3) . . . . ?
C4 C5 C10 C9 -178.51(19) . . . . ?
C8 C9 C10 O2 -179.1(2) . . . . ?
C11 C9 C10 O2 -0.7(3) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
C11 C9 C10 C5 178.47(18) . . . . ?
C8 C9 C11 C12 -168.5(2) . . . . ?
C10 C9 C11 C12 13.1(3) . . . . ?
C9 C11 C12 C13 -179.3(2) . . . . ?
C11 C12 C13 C14 167.8(2) . . . . ?
C11 C12 C13 C18 -10.7(3) . . . . ?
C18 C13 C14 C15 1.2(3) . . . . ?
C12 C13 C14 C15 -177.4(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C14 C15 C16 Br1 -177.98(16) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
Br1 C16 C17 C18 178.56(18) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C12 C13 C18 C17 178.0(2) . . . . ?
C9 C8 C19 C20A -84.0(4) . . . . ?
C7 C8 C19 C20A 94.8(4) . . . . ?
C9 C8 C19 C20B -89.6(7) . . . . ?
C7 C8 C19 C20B 89.1(7) . . . . ?
O3A C20A C19 C8 -58.1(4) . . . . ?
C21 C20A C19 C8 179.6(4) . . . . ?
O3B C20B C19 C8 58.6(8) . . . . ?
C21 C20B C19 C8 174.1(6) . . . . ?
O3A C20A C21 C22 145.3(3) . . . . ?
C19 C20A C21 C22 -97.0(5) . . . . ?
O3A C20A C21 C26 -36.9(4) . . . . ?
C19 C20A C21 C26 80.8(5) . . . . ?
O3B C20B C21 C22 32.7(6) . . . . ?
C19 C20B C21 C22 -89.7(8) . . . . ?
O3B C20B C21 C26 -149.0(5) . . . . ?
C19 C20B C21 C26 88.6(9) . . . . ?
C26 C21 C22 C23 -0.2(4) . . . . ?
C20A C21 C22 C23 177.7(2) . . . . ?
C20B C21 C22 C23 178.1(3) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C25 1.4(4) . . . . ?
C22 C23 C24 Br2 -179.7(2) . . . . ?
C23 C24 C25 C26 -0.9(4) . . . . ?
Br2 C24 C25 C26 -179.80(19) . . . . ?
C22 C21 C26 C25 0.7(4) . . . . ?
C20A C21 C26 C25 -177.1(2) . . . . ?
C20B C21 C26 C25 -177.7(2) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3A^a H3A^a O1 0.84 2.10 2.790(3) 139.5 4_656 yes
O3A^a H3A^a O3A^a 0.84 2.34 2.9824(16) 134.2 4_656 yes

_refine_diff_density_max         0.574
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_p435
_database_code_depnum_ccdc_archive 'CCDC 2222217'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-09-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 N'
_chemical_formula_sum            'C27 H27 N'
_chemical_formula_weight         365.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H27 N'
_chemical_oxdiff_usercomment     P435
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.22731(8)
_cell_length_b                   21.32536(13)
_cell_length_c                   8.10901(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.5065(7)
_cell_angle_gamma                90
_cell_volume                     2037.47(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19162
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4710
_cell_measurement_theta_min      3.7470
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 5 0.3149
2 -1 -5 0.3140
0 1 0 0.2133
0 -1 0 0.2133
-1 0 0 0.0210
1 0 0 0.0267

_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9953 -0.0098 5.0041 0.1760 0.1848 0.9159
1.9948 -0.9906 -5.0043 -0.1342 -0.1291 -0.9352
-0.0002 0.9989 0.0008 -0.0416 -0.0557 0.0193
0.0002 -0.9989 -0.0008 0.0416 0.0557 -0.0193
-1.0004 0.0010 0.0000 0.1039 -0.0793 -0.0044
1.0004 -0.0012 -0.0002 -0.1039 0.0793 0.0043

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.742
_diffrn_reflns_theta_min         3.752
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -16.00   0.50    0.50    --  -48.70 105.00 103.00   94
  2  ω     27.00  70.00   0.50    0.50    --   48.70-105.00   2.00   86
  3  ω    -72.00 -47.00   0.50    2.00    --  -86.25 105.00 103.00   50
  4  ω   -145.00-120.00   0.50    2.00    --  -86.25-105.00   2.00   50
  5  ω    109.00 142.00   0.50    2.00    --  107.75 105.00 103.00   66
  6  ω     54.00 107.00   0.50    2.00    --  107.75-105.00   2.00  106
  7  ω   -108.00 -78.00   0.50    0.50    --  -48.70-125.00  60.00   60
  8  ω   -119.00 -80.00   0.50    0.50    --  -48.70-125.00-150.00   78
  9  ω    -26.00  23.00   0.50    0.50    --  -48.70  19.00-150.00   98
 10  ω    -62.00  23.00   0.50    0.50    --  -48.70  57.00 -90.00  170
 11  ω    -50.00 -16.00   0.50    2.00    --  -86.25  45.00 -30.00   68
 12  ω     37.00  68.00   0.50    2.00    --  107.75 -86.00   7.42   62
 13  ω     97.00 126.00   0.50    2.00    --  107.75  30.00-120.00   58
 14  ω     37.00  68.00   0.50    2.00    --  107.75 -61.00  90.00   62
 15  ω     40.00  90.00   0.50    2.00    --  107.75 -77.00  30.00  100
 16  ω     36.00 105.00   0.50    2.00    --  107.75-110.00 106.00  138
 17  ω    127.00 153.00   0.50    2.00    --  107.75  30.00-120.00   52
 18  ω     60.00 100.00   0.50    2.00    --  107.75-114.00-145.59   80
 19  ω     99.00 125.00   0.50    2.00    --  107.75  15.00  30.00   52
 20  ω    150.00 175.00   0.50    2.00    --  107.75  15.00  30.00   50
 21  ω    100.00 167.00   0.50    2.00    --  107.75  30.00-150.00  134
 22  ω    117.00 154.00   0.50    2.00    --  107.75  45.00  60.00   74
 23  ω     37.00 105.00   0.50    2.00    --  107.75 -95.00  30.00  136
 24  ω     97.00 166.00   0.50    2.00    --  107.75  45.00 150.00  138
 25  ω     84.00 110.00   0.50    2.00    --  107.75 -85.00 -27.22   52
 26  ω     38.00  65.00   0.50    2.00    --  107.75 -61.00 -30.00   54
 27  ω     37.00  63.00   0.50    2.00    --  107.75-125.00  60.00   52
 28  ω     84.00 111.00   0.50    2.00    --  107.75-125.00  60.00   54
 29  ω     67.00  99.00   0.50    2.00    --  107.75-125.00-180.00   64
 30  ω     80.00 105.00   0.50    2.00    --  107.75 -77.00  90.00   50
 31  ω     62.00  94.00   0.50    2.00    --  107.75 -95.00  43.13   64
 32  ω     41.00  70.00   0.50    2.00    --  107.75 -77.00 -90.00   58
 33  ω     97.00 167.00   0.50    2.00    --  107.75  45.00 -30.00  140
 34  ω     47.00 117.00   0.50    2.00    --  107.75-147.00-111.96  140
 35  ω     37.00 111.00   0.50    2.00    --  107.75 -86.00 -94.14  148
 36  ω     68.00  94.00   0.50    2.00    --  107.75 -77.00  60.00   52
 37  ω     36.00  62.00   0.50    2.00    --  107.75-125.00-180.00   52
 38  ω     96.00 128.00   0.50    2.00    --  107.75 -86.00   7.42   64
 39  ω     75.00 108.00   0.50    2.00    --  107.75-125.00 120.00   66
 40  ω     98.00 167.00   0.50    2.00    --  107.75  45.00-120.00  138
 41  ω    118.00 144.00   0.50    2.00    --  107.75  15.00 -30.00   52
 42  ω    119.00 154.00   0.50    2.00    --  107.75  15.00  60.00   70
 43  ω    151.00 177.00   0.50    2.00    --  107.75 125.00 -90.00   52
 44  ω     36.00  68.00   0.50    2.00    --  107.75 -61.00  60.00   64
 45  ω     37.00  69.00   0.50    2.00    --  107.75 -61.00  30.00   64
 46  ω     36.00  61.00   0.50    2.00    --  107.75 -61.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1039161000
_diffrn_orient_matrix_UB_12      -0.0416925000
_diffrn_orient_matrix_UB_13      -0.0063445000
_diffrn_orient_matrix_UB_21      0.0792197000
_diffrn_orient_matrix_UB_22      -0.0557782000
_diffrn_orient_matrix_UB_23      0.0684107000
_diffrn_orient_matrix_UB_31      0.0043907000
_diffrn_orient_matrix_UB_32      0.0192024000
_diffrn_orient_matrix_UB_33      0.1848230000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4145
_reflns_number_total             4338
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.7280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11181(7) 0.68509(4) 0.62133(10) 0.02027(18) Uani 1 1 d . . . . .
H1 H 0.0823(12) 0.7195(7) 0.6565(17) 0.030(3) Uiso 1 1 d . . . . .
C1 C 0.13969(8) 0.55759(5) 0.76772(13) 0.0214(2) Uani 1 1 d . . . . .
H1A H 0.082781 0.551789 0.656263 0.026 Uiso 1 1 calc R U . . .
H1B H 0.102229 0.576756 0.849584 0.026 Uiso 1 1 calc R U . . .
C2 C 0.19591(9) 0.49483(5) 0.83637(15) 0.0291(2) Uani 1 1 d . . . . .
H2A H 0.149375 0.459198 0.778191 0.035 Uiso 1 1 calc R U . . .
H2B H 0.204734 0.491336 0.960990 0.035 Uiso 1 1 calc R U . . .
C3 C 0.31278(8) 0.49489(5) 0.79829(13) 0.0220(2) Uani 1 1 d . . . . .
H3A H 0.372711 0.480043 0.898592 0.026 Uiso 1 1 calc R U . . .
H3B H 0.312199 0.467814 0.698887 0.026 Uiso 1 1 calc R U . . .
C4 C 0.33141(8) 0.56281(4) 0.75945(12) 0.01837(19) Uani 1 1 d . . . . .
C5 C 0.23739(8) 0.59748(4) 0.74835(11) 0.01794(19) Uani 1 1 d . . . . .
C6 C 0.43742(8) 0.58492(4) 0.73180(12) 0.01952(19) Uani 1 1 d . . . . .
H6 H 0.443879 0.628351 0.710142 0.023 Uiso 1 1 calc R U . . .
C7 C 0.52697(8) 0.54801(5) 0.73482(12) 0.0204(2) Uani 1 1 d . . . . .
H7 H 0.520030 0.504737 0.757924 0.024 Uiso 1 1 calc R U . . .
C9 C 0.70988(9) 0.52462(5) 0.67097(13) 0.0245(2) Uani 1 1 d . . . . .
H9 H 0.691090 0.481354 0.669094 0.029 Uiso 1 1 calc R U . . .
C8 C 0.63467(8) 0.56886(5) 0.70546(12) 0.0195(2) Uani 1 1 d . . . . .
C10 C 0.81173(9) 0.54263(5) 0.63930(14) 0.0269(2) Uani 1 1 d . . . . .
H10 H 0.861690 0.511755 0.616295 0.032 Uiso 1 1 calc R U . . .
C11 C 0.84036(8) 0.60539(5) 0.64127(13) 0.0251(2) Uani 1 1 d . . . . .
H11 H 0.909293 0.617954 0.618062 0.030 Uiso 1 1 calc R U . . .
C12 C 0.76716(9) 0.64982(5) 0.67756(15) 0.0284(2) Uani 1 1 d . . . . .
H12 H 0.786729 0.692985 0.680113 0.034 Uiso 1 1 calc R U . . .
C13 C 0.66591(8) 0.63207(5) 0.71012(14) 0.0256(2) Uani 1 1 d . . . . .
H13 H 0.617251 0.663130 0.735856 0.031 Uiso 1 1 calc R U . . .
C14 C 0.22571(8) 0.66747(4) 0.72240(12) 0.01840(19) Uani 1 1 d . . . . .
H14 H 0.282476 0.682204 0.662204 0.022 Uiso 1 1 calc R U . . .
C15 C 0.24723(8) 0.70166(5) 0.89669(13) 0.0217(2) Uani 1 1 d . . . . .
H15A H 0.235636 0.747235 0.876038 0.026 Uiso 1 1 calc R U . . .
H15B H 0.191071 0.687009 0.956286 0.026 Uiso 1 1 calc R U . . .
C16 C 0.36520(8) 0.69069(4) 1.01073(12) 0.0205(2) Uani 1 1 d . . . . .
C17 C 0.38542(9) 0.64820(5) 1.14594(13) 0.0239(2) Uani 1 1 d . . . . .
H17 H 0.323481 0.626572 1.169858 0.029 Uiso 1 1 calc R U . . .
C18 C 0.49515(10) 0.63698(5) 1.24652(14) 0.0284(2) Uani 1 1 d . . . . .
H18 H 0.507542 0.608188 1.339072 0.034 Uiso 1 1 calc R U . . .
C19 C 0.58643(9) 0.66778(5) 1.21182(15) 0.0301(2) Uani 1 1 d . . . . .
H19 H 0.661495 0.659801 1.279357 0.036 Uiso 1 1 calc R U . . .
C20 C 0.56725(9) 0.71024(5) 1.07794(15) 0.0296(2) Uani 1 1 d . . . . .
H20 H 0.629457 0.731468 1.053623 0.036 Uiso 1 1 calc R U . . .
C21 C 0.45746(9) 0.72199(5) 0.97889(14) 0.0255(2) Uani 1 1 d . . . . .
H21 H 0.445231 0.751703 0.888485 0.031 Uiso 1 1 calc R U . . .
C22 C 0.07157(8) 0.67103(4) 0.44885(12) 0.01817(19) Uani 1 1 d . . . . .
C23 C 0.12889(8) 0.63015(5) 0.36548(12) 0.0202(2) Uani 1 1 d . . . . .
H23 H 0.199825 0.612806 0.426049 0.024 Uiso 1 1 calc R U . . .
C24 C 0.08231(9) 0.61484(5) 0.19427(13) 0.0232(2) Uani 1 1 d . . . . .
H24 H 0.121561 0.586528 0.139880 0.028 Uiso 1 1 calc R U . . .
C25 C -0.02019(9) 0.64004(5) 0.10135(13) 0.0243(2) Uani 1 1 d . . . . .
H25 H -0.051157 0.629434 -0.015638 0.029 Uiso 1 1 calc R U . . .
C26 C -0.07663(8) 0.68120(5) 0.18332(13) 0.0234(2) Uani 1 1 d . . . . .
H26 H -0.146930 0.698868 0.121320 0.028 Uiso 1 1 calc R U . . .
C27 C -0.03205(8) 0.69686(5) 0.35384(13) 0.0213(2) Uani 1 1 d . . . . .
H27 H -0.071764 0.725292 0.407148 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.897(14) . ?
N1 C14 1.4636(12) . ?
N1 C22 1.3857(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5393(14) . ?
C1 C5 1.5084(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5405(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5125(13) . ?
C4 C5 1.3494(13) . ?
C4 C6 1.4518(13) . ?
C5 C14 1.5088(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.3433(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.4684(13) . ?
C9 H9 0.9500 . ?
C9 C8 1.3969(14) . ?
C9 C10 1.3912(14) . ?
C8 C13 1.3989(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3823(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3879(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3858(14) . ?
C13 H13 0.9500 . ?
C14 H14 1.0000 . ?
C14 C15 1.5490(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5090(13) . ?
C16 C17 1.3926(14) . ?
C16 C21 1.3932(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.3919(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3871(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3848(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3905(15) . ?
C21 H21 0.9500 . ?
C22 C23 1.4006(13) . ?
C22 C27 1.4073(13) . ?
C23 H23 0.9500 . ?
C23 C24 1.3913(14) . ?
C24 H24 0.9500 . ?
C24 C25 1.3865(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.3906(15) . ?
C26 H26 0.9500 . ?
C26 C27 1.3847(14) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N1 H1 115.8(9) . . ?
C22 N1 H1 115.7(9) . . ?
C22 N1 C14 122.51(8) . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
C5 C1 H1A 111.0 . . ?
C5 C1 H1B 111.0 . . ?
C5 C1 C2 103.80(8) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C1 C2 C3 105.98(8) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 104.00(8) . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C5 C4 C3 111.43(8) . . ?
C5 C4 C6 126.28(9) . . ?
C6 C4 C3 122.24(8) . . ?
C1 C5 C14 121.62(8) . . ?
C4 C5 C1 111.62(8) . . ?
C4 C5 C14 126.76(9) . . ?
C4 C6 H6 117.8 . . ?
C7 C6 C4 124.33(9) . . ?
C7 C6 H6 117.8 . . ?
C6 C7 H7 117.2 . . ?
C6 C7 C8 125.57(9) . . ?
C8 C7 H7 117.2 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C10 C9 C8 121.35(10) . . ?
C9 C8 C7 119.67(9) . . ?
C9 C8 C13 117.82(9) . . ?
C13 C8 C7 122.52(9) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.10(10) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.19(9) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.91(10) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.62(10) . . ?
C12 C13 H13 119.7 . . ?
N1 C14 C5 111.87(8) . . ?
N1 C14 H14 109.1 . . ?
N1 C14 C15 107.11(7) . . ?
C5 C14 H14 109.1 . . ?
C5 C14 C15 110.60(8) . . ?
C15 C14 H14 109.1 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.80(8) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C17 C16 C15 121.52(9) . . ?
C17 C16 C21 118.40(9) . . ?
C21 C16 C15 120.06(9) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.91(10) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.11(10) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.46(10) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.38(10) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.74(10) . . ?
C20 C21 H21 119.6 . . ?
N1 C22 C23 122.24(9) . . ?
N1 C22 C27 119.51(9) . . ?
C23 C22 C27 118.22(9) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.24(9) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.38(9) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 120.8 . . ?
C24 C25 C26 118.49(9) . . ?
C26 C25 H25 120.8 . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.09(9) . . ?
C27 C26 H26 119.5 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.58(9) . . ?
C26 C27 H27 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C14 C15 C16 -176.56(8) . . . . ?
N1 C22 C23 C24 176.63(9) . . . . ?
N1 C22 C27 C26 -176.97(9) . . . . ?
C1 C2 C3 C4 15.90(11) . . . . ?
C1 C5 C14 N1 -34.19(12) . . . . ?
C1 C5 C14 C15 85.11(10) . . . . ?
C2 C1 C5 C4 13.34(11) . . . . ?
C2 C1 C5 C14 -165.91(9) . . . . ?
C2 C3 C4 C5 -8.18(11) . . . . ?
C2 C3 C4 C6 174.14(9) . . . . ?
C3 C4 C5 C1 -3.31(11) . . . . ?
C3 C4 C5 C14 175.89(9) . . . . ?
C3 C4 C6 C7 1.20(15) . . . . ?
C4 C5 C14 N1 146.68(9) . . . . ?
C4 C5 C14 C15 -94.02(11) . . . . ?
C4 C6 C7 C8 179.27(9) . . . . ?
C5 C1 C2 C3 -17.63(11) . . . . ?
C5 C4 C6 C7 -176.12(10) . . . . ?
C5 C14 C15 C16 61.30(11) . . . . ?
C6 C4 C5 C1 174.25(9) . . . . ?
C6 C4 C5 C14 -6.54(16) . . . . ?
C6 C7 C8 C9 -164.50(10) . . . . ?
C6 C7 C8 C13 15.35(16) . . . . ?
C7 C8 C13 C12 -178.42(10) . . . . ?
C9 C8 C13 C12 1.43(15) . . . . ?
C9 C10 C11 C12 0.93(16) . . . . ?
C8 C9 C10 C11 -0.10(16) . . . . ?
C10 C9 C8 C7 178.78(9) . . . . ?
C10 C9 C8 C13 -1.08(15) . . . . ?
C10 C11 C12 C13 -0.57(16) . . . . ?
C11 C12 C13 C8 -0.63(17) . . . . ?
C14 N1 C22 C23 10.93(14) . . . . ?
C14 N1 C22 C27 -171.06(9) . . . . ?
C14 C15 C16 C17 -101.79(11) . . . . ?
C14 C15 C16 C21 76.28(11) . . . . ?
C15 C16 C17 C18 177.81(9) . . . . ?
C15 C16 C21 C20 -177.03(9) . . . . ?
C16 C17 C18 C19 -0.66(16) . . . . ?
C17 C16 C21 C20 1.10(15) . . . . ?
C17 C18 C19 C20 0.81(16) . . . . ?
C18 C19 C20 C21 -0.01(17) . . . . ?
C19 C20 C21 C16 -0.97(16) . . . . ?
C21 C16 C17 C18 -0.29(15) . . . . ?
C22 N1 C14 C5 -69.13(11) . . . . ?
C22 N1 C14 C15 169.53(8) . . . . ?
C22 C23 C24 C25 0.99(15) . . . . ?
C23 C22 C27 C26 1.12(14) . . . . ?
C23 C24 C25 C26 -0.26(15) . . . . ?
C24 C25 C26 C27 -0.03(15) . . . . ?
C25 C26 C27 C22 -0.41(15) . . . . ?
C27 C22 C23 C24 -1.40(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.847
####################################################################### 
# 
# 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_p481
_database_code_depnum_ccdc_archive 'CCDC 2222213'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O7'
_chemical_formula_sum            'C18 H16 O7'
_chemical_formula_weight         344.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     P481
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.94730(10)
_cell_length_b                   13.4572(2)
_cell_length_c                   23.6162(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.7680(10)
_cell_angle_gamma                90
_cell_volume                     1570.46(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24448
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.8860
_cell_measurement_theta_min      3.7280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0054
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5674
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.779
_diffrn_reflns_theta_min         3.748
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -6.00   0.40    0.60    --  -48.68 114.00-150.00  190
  2  ω     27.00  89.00   0.40    0.60    --   48.68-114.00 118.00  155
  3  ω    -83.00 -15.00   0.40    2.40    --  -86.25 114.00-150.00  170
  4  ω   -158.00 -80.00   0.40    2.40    --  -86.25-114.00 118.00  195
  5  ω    102.00 178.00   0.40    2.40    --  107.75 114.00-150.00  190
  6  ω     72.00 100.00   0.40    2.40    --  107.75-114.00 118.00   70
  7  ω    -45.00 -19.80   0.40    0.60    --  -48.68 125.00-180.00   63
  8  ω    -84.00 -56.00   0.40    0.60    --  -48.68 125.00-180.00   70
  9  ω    -22.00   9.20   0.40    0.60    --  -48.68  19.00  60.00   78
 10  ω    -26.00  26.00   0.40    0.60    --  -48.68  19.00-120.00  130
 11  ω    -22.00  16.00   0.40    0.60    --  -48.68  19.00  90.00   95
 12  ω    -69.00 -43.80   0.40    0.60    --  -48.68  77.00 -60.00   63
 13  ω   -120.00 -74.80   0.40    0.60    --  -48.68-125.00 -60.00  113
 14  ω    -42.00  23.20   0.40    0.60    --  -48.68  38.00 -90.00  163
 15  ω    -26.00  25.20   0.40    0.60    --  -48.68  19.00 120.00  128
 16  ω    -15.00  12.20   0.40    0.60    --  -48.68  77.00 -60.00   68
 17  ω   -147.00-113.80   0.40    2.40    --  -86.25 -15.00   0.00   83
 18  ω    -50.00 -16.80   0.40    2.40    --  -86.25  45.00  60.00   83
 19  ω     55.00  80.20   0.40    2.40    --  107.75-147.00-107.69   63
 20  ω     99.00 135.00   0.40    2.40    --  107.75  61.00-180.00   90
 21  ω     99.00 130.20   0.40    2.40    --  107.75-156.00  91.67   78
 22  ω     41.00  68.20   0.40    2.40    --  107.75-125.00-120.00   68
 23  ω     97.00 134.20   0.40    2.40    --  107.75  45.00-150.00   93
 24  ω     50.00  76.00   0.40    2.40    --  107.75-156.00  91.67   65
 25  ω     40.00  66.00   0.40    2.40    --  107.75 -61.00 -90.00   65
 26  ω     48.00  94.00   0.40    2.40    --  107.75 -95.00 120.00  115
 27  ω    103.00 177.00   0.40    2.40    --  107.75  61.00   0.00  185
 28  ω     37.00  63.00   0.40    2.40    --  107.75 -61.00  30.00   65
 29  ω     85.00 110.20   0.40    2.40    --  107.75-125.00  60.00   63
 30  ω    147.00 172.20   0.40    2.40    --  107.75  45.00-150.00   63
 31  ω     36.00  73.20   0.40    2.40    --  107.75-125.00  30.00   93
 32  ω     82.00 108.00   0.40    2.40    --  107.75-125.00  30.00   65
 33  ω     48.00  74.00   0.40    2.40    --  107.75 -77.00-150.00   65
 34  ω     82.00 107.20   0.40    2.40    --  107.75-110.00 -90.37   63
 35  ω     94.00 130.00   0.40    2.40    --  107.75  61.00 120.00   90
 36  ω     92.00 128.00   0.40    2.40    --  107.75-147.00-107.69   90
 37  ω     97.00 127.80   0.40    2.40    --  107.75  61.00  60.00   77
 38  ω     76.80 106.00   0.40    2.40    --  107.75 -94.00 176.47   73
 39  ω     41.00  99.00   0.40    2.40    --  107.75 -95.00-110.85  145
 40  ω     45.00  77.00   0.40    2.40    --  107.75 -77.00-180.00   80
 41  ω     53.00 103.00   0.40    2.40    --  107.75 -77.00 -90.00  125
 42  ω     36.00  75.20   0.40    2.40    --  107.75 -77.00-120.00   98
 43  ω    129.00 155.00   0.40    2.40    --  107.75  30.00   0.00   65
 44  ω     36.00  61.20   0.40    2.40    --  107.75 -94.00 176.47   63
 45  ω    101.00 157.00   0.40    2.40    --  107.75 125.00 -30.00  140
 46  ω    140.00 166.00   0.40    2.40    --  107.75  30.00  60.00   65
 47  ω    142.00 174.00   0.40    2.40    --  107.75  61.00  60.00   80
 48  ω     98.00 174.00   0.40    2.40    --  107.75  45.00   0.00  190
 49  ω     73.00  99.00   0.40    2.40    --  107.75 -95.00  30.00   65
 50  ω     36.00  62.00   0.40    2.40    --  107.75 -77.00  60.00   65
 51  ω     94.00 177.20   0.40    2.40    --  107.75  61.00  30.00  208
 52  ω     37.00  76.20   0.40    2.40    --  107.75-125.00  60.00   98
 53  ω    105.00 152.20   0.40    2.40    --  107.75  45.00 150.00  118
 54  ω    116.00 142.00   0.40    2.40    --  107.75  30.00 -60.00   65
 55  ω     42.00  83.20   0.40    2.40    --  107.75 -77.00 120.00  103
 56  ω     60.00 103.20   0.40    2.40    --  107.75 -95.00  60.00  108
 57  ω    115.00 173.00   0.40    2.40    --  107.75  77.00-180.00  145
 58  ω     37.00  63.00   0.40    2.40    --  107.75-125.00-150.00   65
 59  ω     82.00 110.00   0.40    2.40    --  107.75-125.00-150.00   70
 60  ω     42.00  67.20   0.40    2.40    --  107.75 -61.00 150.00   63
 61  ω     72.00 101.20   0.40    2.40    --  107.75 -96.00 157.13   73
 62  ω     60.00  86.00   0.40    2.40    --  107.75 -95.00   0.00   65
 63  ω     36.00  67.20   0.40    2.40    --  107.75 -95.00  90.00   78
 64  ω     56.00  82.00   0.40    2.40    --  107.75-108.00 -54.27   65
 65  ω     75.00 100.20   0.40    2.40    --  107.75 -95.00-150.00   63
 66  ω    140.00 171.20   0.40    2.40    --  107.75  61.00 120.00   78
 67  ω     40.00  66.00   0.40    2.40    --  107.75 -84.00  15.97   65
 68  ω     92.00 130.00   0.40    2.40    --  107.75 -84.00  15.97   95
 69  ω     45.00  70.20   0.40    2.40    --  107.75 -96.00 157.13   63
 70  ω     37.00  63.00   0.40    2.40    --  107.75 -61.00 120.00   65
 71  ω     42.00  68.00   0.40    2.40    --  107.75-125.00 150.00   65
 72  ω     67.00 107.00   0.40    2.40    --  107.75 -78.00-112.01  100
 73  ω    122.00 148.00   0.40    2.40    --  107.75  45.00-180.00   65
 74  ω    114.00 139.20   0.40    2.40    --  107.75  45.00-120.00   63
 75  ω     98.00 145.20   0.40    2.40    --  107.75  45.00 -30.00  118
 76  ω     98.00 134.00   0.40    2.40    --  107.75  45.00  30.00   90
 77  ω     36.00  68.00   0.40    2.40    --  107.75 -61.00 -30.00   80
 78  ω    108.00 134.00   0.40    2.40    --  107.75 125.00   0.00   65
 79  ω    122.00 148.00   0.40    2.40    --  107.75 125.00 150.00   65
 80  ω     96.00 128.00   0.40    2.40    --  107.75  77.00-120.00   80
 81  ω    134.00 174.00   0.40    2.40    --  107.75  77.00-120.00  100
 82  ω     48.00  74.00   0.40    2.40    --  107.75 -80.00 167.75   65
 83  ω     82.00 108.00   0.40    2.40    --  107.75 -80.00 167.75   65
 84  ω     84.00 110.00   0.40    2.40    --  107.75 -84.00-178.01   65
 85  ω    103.00 129.00   0.40    2.40    --  107.75  48.00 -71.59   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0724339000
_diffrn_orient_matrix_UB_12      -0.1083641000
_diffrn_orient_matrix_UB_13      -0.0152572000
_diffrn_orient_matrix_UB_21      -0.0583119000
_diffrn_orient_matrix_UB_22      0.0307702000
_diffrn_orient_matrix_UB_23      -0.0622206000
_diffrn_orient_matrix_UB_31      0.2976055000
_diffrn_orient_matrix_UB_32      -0.0203268000
_diffrn_orient_matrix_UB_33      -0.0126979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5497
_reflns_number_total             5674
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.3701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1038
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5889(11)
 0.4111(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C11(H11), C12(H12)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0966(2) 0.14427(7) 0.56553(4) 0.0294(2) Uani 1 1 d . . . . .
C1 C 0.1909(3) 0.00888(10) 0.63570(6) 0.0244(3) Uani 1 1 d . . . . .
H1 H 0.045422 -0.017318 0.612579 0.029 Uiso 1 1 calc R U . . .
O2 O 0.7276(2) 0.28710(8) 0.69367(5) 0.0399(3) Uani 1 1 d . . . . .
C2 C 0.3430(3) -0.05319(10) 0.67160(6) 0.0266(3) Uani 1 1 d . . . . .
H2 H 0.301715 -0.122062 0.673020 0.032 Uiso 1 1 calc R U . . .
O3 O -0.0847(2) 0.41241(7) 0.45824(4) 0.0302(3) Uani 1 1 d . . . . .
H3 H -0.182(5) 0.3711(19) 0.4403(11) 0.059(7) Uiso 1 1 d . . . . .
C3 C 0.5553(3) -0.01514(10) 0.70545(6) 0.0251(3) Uani 1 1 d . . . . .
H3A H 0.658581 -0.058084 0.729996 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6178(3) 0.08555(10) 0.70368(5) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.763453 0.111408 0.726894 0.027 Uiso 1 1 calc R U . . .
O4 O -0.00324(19) 0.21878(7) 0.43146(4) 0.0238(2) Uani 1 1 d . . . . .
O5 O 0.37292(18) 0.21510(7) 0.48903(4) 0.0214(2) Uani 1 1 d . . . . .
C5 C 0.4657(3) 0.14825(9) 0.66766(5) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.2520(3) 0.10980(9) 0.63366(5) 0.0196(3) Uani 1 1 d . . . . .
O6 O 0.4874(2) 0.64395(7) 0.62461(5) 0.0331(3) Uani 1 1 d . . . . .
C7 C 0.0913(3) 0.17663(9) 0.59541(5) 0.0207(3) Uani 1 1 d . . . . .
O7 O 0.81377(19) 0.62426(6) 0.69276(4) 0.0236(2) Uani 1 1 d . . . . .
C9 C 0.3640(3) 0.32362(9) 0.62788(5) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.1579(3) 0.28533(9) 0.59404(5) 0.0186(2) Uani 1 1 d . . . . .
C10 C 0.5330(3) 0.25581(10) 0.66544(5) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.4190(3) 0.43083(9) 0.62797(5) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.299441 0.470120 0.604601 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6160(3) 0.48029(9) 0.65673(5) 0.0212(3) Uani 1 1 d . . . . .
H12 H 0.749554 0.444655 0.678686 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6272(3) 0.58996(9) 0.65458(5) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.8226(3) 0.73115(10) 0.69855(6) 0.0288(3) Uani 1 1 d . . . . .
H14A H 0.955509 0.749284 0.728912 0.043 Uiso 1 1 calc R U . . .
H14B H 0.643654 0.755713 0.707853 0.043 Uiso 1 1 calc R U . . .
H14C H 0.874739 0.760913 0.662808 0.043 Uiso 1 1 calc R U . . .
C15 C -0.0185(3) 0.34478(9) 0.55274(5) 0.0208(3) Uani 1 1 d . . . . .
H15A H -0.047254 0.411508 0.569041 0.025 Uiso 1 1 calc R U . . .
H15B H -0.197276 0.311960 0.548203 0.025 Uiso 1 1 calc R U . . .
C16 C 0.0981(3) 0.35736(9) 0.49326(5) 0.0204(3) Uani 1 1 d . . . . .
H16 H 0.273544 0.394158 0.497316 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1474(3) 0.25664(9) 0.46693(5) 0.0191(3) Uani 1 1 d . . . . .
C18 C 0.4274(3) 0.11648(11) 0.46831(7) 0.0312(3) Uani 1 1 d . . . . .
H18A H 0.601262 0.093128 0.484955 0.047 Uiso 1 1 calc R U . . .
H18B H 0.434756 0.118152 0.426925 0.047 Uiso 1 1 calc R U . . .
H18C H 0.283205 0.071256 0.478985 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2201(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C6 1.3926(18) . ?
O2 C10 1.2191(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
O3 H3 0.84(3) . ?
O3 C16 1.4064(14) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3910(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3930(18) . ?
O4 C17 1.2069(16) . ?
O5 C17 1.3316(15) . ?
O5 C18 1.4443(15) . ?
C5 C6 1.3956(17) . ?
C5 C10 1.4869(17) . ?
C6 C7 1.4791(18) . ?
O6 C13 1.2083(16) . ?
C7 C8 1.5001(17) . ?
O7 C13 1.3406(15) . ?
O7 C14 1.4453(15) . ?
C9 C8 1.3657(17) . ?
C9 C10 1.4991(17) . ?
C9 C11 1.4682(17) . ?
C8 C15 1.5067(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3379(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.4778(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5531(18) . ?
C16 H16 1.0000 . ?
C16 C17 1.5159(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.76(12) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.25(12) . . ?
C3 C2 H2 119.9 . . ?
C16 O3 H3 106.6(17) . . ?
C2 C3 H3A 119.8 . . ?
C2 C3 C4 120.38(12) . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.60(12) . . ?
C5 C4 H4 120.2 . . ?
C17 O5 C18 114.81(10) . . ?
C4 C5 C6 119.92(12) . . ?
C4 C5 C10 119.72(12) . . ?
C6 C5 C10 120.36(11) . . ?
C1 C6 C5 120.09(12) . . ?
C1 C6 C7 120.19(11) . . ?
C5 C6 C7 119.72(11) . . ?
O1 C7 C6 120.55(11) . . ?
O1 C7 C8 119.83(12) . . ?
C6 C7 C8 119.61(11) . . ?
C13 O7 C14 115.03(10) . . ?
C8 C9 C10 119.74(11) . . ?
C8 C9 C11 120.31(11) . . ?
C11 C9 C10 119.94(11) . . ?
C7 C8 C15 114.26(11) . . ?
C9 C8 C7 120.91(11) . . ?
C9 C8 C15 124.82(11) . . ?
O2 C10 C5 119.30(12) . . ?
O2 C10 C9 121.10(12) . . ?
C5 C10 C9 119.59(11) . . ?
C9 C11 H11 115.8 . . ?
C12 C11 C9 128.32(12) . . ?
C12 C11 H11 115.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.47(11) . . ?
C13 C12 H12 119.8 . . ?
O6 C13 O7 122.88(12) . . ?
O6 C13 C12 126.81(12) . . ?
O7 C13 C12 110.29(10) . . ?
O7 C14 H14A 109.5 . . ?
O7 C14 H14B 109.5 . . ?
O7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 108.6 . . ?
C8 C15 H15B 108.6 . . ?
C8 C15 C16 114.50(10) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
O3 C16 C15 109.45(11) . . ?
O3 C16 H16 109.0 . . ?
O3 C16 C17 109.96(10) . . ?
C15 C16 H16 109.0 . . ?
C17 C16 C15 110.35(10) . . ?
C17 C16 H16 109.0 . . ?
O4 C17 O5 124.92(12) . . ?
O4 C17 C16 123.77(11) . . ?
O5 C17 C16 111.29(10) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O4 0.84(3) 2.25(3) 2.7159(13) 116(2) . yes
O3 H3 O6 0.84(3) 2.11(3) 2.8281(14) 144(2) 3_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 178.74(13) . . . . ?
O1 C7 C8 C15 -1.68(17) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C6 C7 O1 0.32(19) . . . . ?
C1 C6 C7 C8 179.44(12) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 C7 179.87(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
O3 C16 C17 O4 -20.14(18) . . . . ?
O3 C16 C17 O5 161.44(11) . . . . ?
C3 C4 C5 C6 -0.01(19) . . . . ?
C3 C4 C5 C10 -179.66(12) . . . . ?
C4 C5 C6 C1 0.00(19) . . . . ?
C4 C5 C6 C7 -179.90(11) . . . . ?
C4 C5 C10 O2 2.8(2) . . . . ?
C4 C5 C10 C9 -178.25(12) . . . . ?
C5 C6 C7 O1 -179.78(12) . . . . ?
C5 C6 C7 C8 -0.66(17) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C6 C5 C10 O2 -176.88(13) . . . . ?
C6 C5 C10 C9 2.10(18) . . . . ?
C6 C7 C8 C9 -0.39(18) . . . . ?
C6 C7 C8 C15 179.20(11) . . . . ?
C7 C8 C15 C16 -93.23(13) . . . . ?
C9 C8 C15 C16 86.33(15) . . . . ?
C9 C11 C12 C13 -175.51(12) . . . . ?
C8 C9 C10 O2 175.84(14) . . . . ?
C8 C9 C10 C5 -3.13(18) . . . . ?
C8 C9 C11 C12 -177.63(13) . . . . ?
C8 C15 C16 O3 179.07(10) . . . . ?
C8 C15 C16 C17 57.92(14) . . . . ?
C10 C5 C6 C1 179.65(12) . . . . ?
C10 C5 C6 C7 -0.25(18) . . . . ?
C10 C9 C8 C7 2.25(18) . . . . ?
C10 C9 C8 C15 -177.29(11) . . . . ?
C10 C9 C11 C12 2.9(2) . . . . ?
C11 C9 C8 C7 -177.25(11) . . . . ?
C11 C9 C8 C15 3.21(19) . . . . ?
C11 C9 C10 O2 -4.7(2) . . . . ?
C11 C9 C10 C5 176.38(11) . . . . ?
C11 C12 C13 O6 -7.4(2) . . . . ?
C11 C12 C13 O7 170.69(12) . . . . ?
C14 O7 C13 O6 4.3(2) . . . . ?
C14 O7 C13 C12 -173.81(11) . . . . ?
C15 C16 C17 O4 100.70(14) . . . . ?
C15 C16 C17 O5 -77.72(13) . . . . ?
C18 O5 C17 O4 -1.47(19) . . . . ?
C18 O5 C17 C16 176.93(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.464
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5889(11) 13654 20063 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4111(11) 13689 20063 nmt 0.9995 0.0000 0.0000 0.0009 -1.0000 0.0003 -0.4475
-0.0017 -1.0002

_twin_special_details            
;
Component 2 rotated by -179.9426° 
around [0.98 0.00 -0.22] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
####################################################################### 
# 
# 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_p491
_database_code_depnum_ccdc_archive 'CCDC 2222215'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-09-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 N'
_chemical_formula_sum            'C24 H25 N'
_chemical_formula_weight         327.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H25N
_chemical_oxdiff_usercomment     P491
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.58245(2)
_cell_length_b                   19.16935(9)
_cell_length_c                   34.33220(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3673.95(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    30517
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.5900
_cell_measurement_theta_min      2.5860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            47670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.701
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   1.00   0.50    4.20    --  -48.68  18.00 102.00   50
  2  ω    -95.00 -56.00   0.50    4.20    --  -48.68 155.00  98.00   78
  3  ω   -123.00 -55.00   0.50    4.20    --  -48.68 -18.00 -65.00  136
  4  ω    -24.00   1.00   0.50    4.20    --   48.68 -18.00 -65.00   50
  5  ω    -64.00 -39.00   0.50    4.20    --  -48.70 -18.00 -65.00   50
  6  ω     69.00  94.00   0.50    4.20    --   48.70  18.00 102.00   50
  7  ω    -72.00 -47.00   0.50   16.80    --  -86.25 111.00-145.00   50
  8  ω    -92.00 -67.00   0.50   16.80    --  -86.25 155.00  98.00   50
  9  ω   -142.00-117.00   0.50   16.80    --  -86.25 -18.00 -65.00   50
 10  ω     99.00 138.00   0.50   16.80    --  107.75  18.00 102.00   78
 11  ω     79.00 105.00   0.50   16.80    --  107.75-120.00-142.00   52
 12  ω     46.00  72.00   0.50   16.80    --  107.75-120.00-142.00   52
 13  ω     81.00 120.00   0.50   16.80    --  107.75 155.00  98.00   78
 14  ω     72.00  98.00   0.50   16.80    --  107.75-111.00 120.00   52
 15  ω    138.00 174.00   0.50   16.80    --  107.75 120.00 -58.00   72
 16  ω    121.00 147.00   0.50   16.80    --  107.75 111.00-145.00   52
 17  ω    -15.00  12.00   0.50    4.20    --  -48.70  19.00-120.00   54
 18  ω    -20.00  25.00   0.50    4.20    --   48.70 -19.00-180.00   90
 19  ω   -144.00-119.00   0.50   16.80    --  -86.25-111.00 120.00   50
 20  ω     41.00  66.00   0.50   16.80    --  107.75 -77.00-120.00   50
 21  ω    153.00 178.00   0.50   16.80    --  107.75  77.00   0.00   50
 22  ω     74.00 109.00   0.50   16.80    --  107.75-123.00 -12.80   70
 23  ω     87.00 112.00   0.50   16.80    --  107.75  77.00   0.00   50
 24  ω     42.00  67.00   0.50   16.80    --  107.75 -61.00  90.00   50
 25  ω     36.00  77.00   0.50   16.80    --  107.75 -95.00  30.00   82
 26  ω     99.00 176.00   0.50   16.80    --  107.75  45.00  30.00  154
 27  ω     53.00  87.00   0.50   16.80    --  107.75-125.00 -30.00   68
 28  ω     37.00 109.00   0.50   16.80    --  107.75 -81.00 -48.65  144
 29  ω     38.00  64.00   0.50   16.80    --  107.75 -61.00-120.00   52
 30  ω     79.00 104.00   0.50   16.80    --  107.75 -77.00  30.00   50
 31  ω     36.00 107.00   0.50   16.80    --  107.75-111.00  23.51  142
 32  ω    125.00 174.00   0.50   16.80    --  107.75 125.00 -90.00   98
 33  ω    105.00 130.00   0.50   16.80    --  107.75  30.00 -90.00   50
 34  ω    131.00 178.00   0.50   16.80    --  107.75  30.00 -90.00   94
 35  ω     77.00 104.00   0.50   16.80    --  107.75 -77.00-150.00   54
 36  ω     47.00  72.00   0.50   16.80    --  107.75-125.00   0.00   50
 37  ω     81.00 111.00   0.50   16.80    --  107.75-125.00   0.00   60
 38  ω    132.00 175.00   0.50   16.80    --  107.75 125.00-120.00   86
 39  ω     98.00 140.00   0.50   16.80    --  107.75  45.00 -60.00   84
 40  ω    145.00 178.00   0.50   16.80    --  107.75  45.00 -60.00   66
 41  ω    128.00 178.00   0.50   16.80    --  107.75  61.00-120.00  100
 42  ω     60.00 109.00   0.50   16.80    --  107.75-115.00  79.59   98
 43  ω     94.00 164.00   0.50   16.80    --  107.75  61.00-150.00  140
 44  ω     38.00  70.00   0.50   16.80    --  107.75 -61.00 -30.00   64
 45  ω     41.00  66.00   0.50   16.80    --  107.75 -61.00  60.00   50
 46  ω     72.00 110.00   0.50   16.80    --  107.75-125.00 120.00   76
 47  ω     62.00  88.00   0.50   16.80    --  107.75 -77.00-180.00   52
 48  ω     73.00  99.00   0.50   16.80    --  107.75 -77.00-120.00   52
 49  ω    120.00 168.00   0.50   16.80    --  107.75  77.00 -90.00   96
 50  ω     65.00  91.00   0.50   16.80    --  107.75 -95.00  60.00   52
 51  ω     55.00  98.00   0.50   16.80    --  107.75-120.00  65.50   86
 52  ω    114.00 140.00   0.50   16.80    --  107.75  45.00 150.00   52
 53  ω    126.00 152.00   0.50   16.80    --  107.75  15.00-150.00   52
 54  ω    142.00 167.00   0.50   16.80    --  107.75 144.00-163.04   50
 55  ω     36.00  71.00   0.50   16.80    --  107.75 -61.00   0.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0620516000
_diffrn_orient_matrix_UB_12      -0.0768387000
_diffrn_orient_matrix_UB_13      0.0083414000
_diffrn_orient_matrix_UB_21      0.0204894000
_diffrn_orient_matrix_UB_22      0.0166503000
_diffrn_orient_matrix_UB_23      0.0437719000
_diffrn_orient_matrix_UB_31      -0.2682132000
_diffrn_orient_matrix_UB_32      -0.0165211000
_diffrn_orient_matrix_UB_33      0.0052860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3665
_reflns_number_total             3877
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.2405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0946
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.89635(15) 0.45731(4) 0.45091(2) 0.02133(18) Uani 1 1 d . . . . .
C1 C 0.96558(17) 0.38546(5) 0.34723(3) 0.0199(2) Uani 1 1 d . . . . .
C2 C 1.09989(18) 0.32578(5) 0.33909(3) 0.0231(2) Uani 1 1 d . . . . .
H2 H 1.232619 0.314622 0.355250 0.028 Uiso 1 1 calc R U . . .
C3 C 1.04486(19) 0.28237(5) 0.30809(3) 0.0247(2) Uani 1 1 d . . . . .
H3 H 1.138079 0.241839 0.303220 0.030 Uiso 1 1 calc R U . . .
C4 C 0.85219(19) 0.29870(5) 0.28421(3) 0.0245(2) Uani 1 1 d . . . . .
H4 H 0.812224 0.269100 0.262992 0.029 Uiso 1 1 calc R U . . .
C6 C 0.77037(17) 0.40256(5) 0.32274(3) 0.0202(2) Uani 1 1 d . . . . .
C5 C 0.71839(18) 0.35809(5) 0.29134(3) 0.0233(2) Uani 1 1 d . . . . .
H5 H 0.588245 0.369063 0.274596 0.028 Uiso 1 1 calc R U . . .
C7 C 0.62477(17) 0.46535(5) 0.32981(3) 0.0216(2) Uani 1 1 d . . . . .
H7 H 0.674741 0.494949 0.350463 0.026 Uiso 1 1 calc R U . . .
C8 C 0.42930(17) 0.48494(5) 0.31012(3) 0.0215(2) Uani 1 1 d . . . . .
H8 H 0.380557 0.455944 0.289124 0.026 Uiso 1 1 calc R U . . .
C9 C 0.28293(17) 0.54706(5) 0.31789(3) 0.0204(2) Uani 1 1 d . . . . .
C10 C 0.08863(18) 0.56183(5) 0.29345(3) 0.0246(2) Uani 1 1 d . . . . .
H10 H 0.059820 0.533004 0.271437 0.029 Uiso 1 1 calc R U . . .
C11 C -0.06299(19) 0.61786(6) 0.30077(3) 0.0278(2) Uani 1 1 d . . . . .
H11 H -0.193281 0.627072 0.283733 0.033 Uiso 1 1 calc R U . . .
C12 C -0.02467(18) 0.66034(5) 0.33286(3) 0.0263(2) Uani 1 1 d . . . . .
H12 H -0.129874 0.698107 0.338191 0.032 Uiso 1 1 calc R U . . .
C13 C 0.16982(18) 0.64706(5) 0.35720(3) 0.0244(2) Uani 1 1 d . . . . .
H13 H 0.198101 0.676247 0.379087 0.029 Uiso 1 1 calc R U . . .
C14 C 0.32228(18) 0.59160(5) 0.34973(3) 0.0225(2) Uani 1 1 d . . . . .
H14 H 0.455338 0.583589 0.366392 0.027 Uiso 1 1 calc R U . . .
C15 C 1.02619(17) 0.42815(5) 0.38297(3) 0.0205(2) Uani 1 1 d . . . . .
H15A H 1.009088 0.478352 0.376800 0.025 Uiso 1 1 calc R U . . .
H15B H 1.195052 0.419553 0.390356 0.025 Uiso 1 1 calc R U . . .
C16 C 0.86129(16) 0.40960(5) 0.41769(3) 0.01841(19) Uani 1 1 d . . . . .
H16 H 0.691163 0.413591 0.408850 0.022 Uiso 1 1 calc R U . . .
C17 C 0.90668(16) 0.33449(5) 0.42969(3) 0.01717(18) Uani 1 1 d . . . . .
C18 C 0.74909(17) 0.28191(5) 0.41880(3) 0.0212(2) Uani 1 1 d . . . . .
H18 H 0.607839 0.293417 0.404765 0.025 Uiso 1 1 calc R U . . .
C19 C 0.79549(19) 0.21261(5) 0.42818(3) 0.0248(2) Uani 1 1 d . . . . .
H19 H 0.686754 0.177141 0.420372 0.030 Uiso 1 1 calc R U . . .
C20 C 0.99999(18) 0.19522(5) 0.44888(3) 0.0231(2) Uani 1 1 d . . . . .
H20 H 1.031816 0.147893 0.455250 0.028 Uiso 1 1 calc R U . . .
C21 C 1.15848(17) 0.24733(5) 0.46029(3) 0.0224(2) Uani 1 1 d . . . . .
H21 H 1.298032 0.235713 0.474737 0.027 Uiso 1 1 calc R U . . .
C22 C 1.11254(17) 0.31636(5) 0.45054(3) 0.0206(2) Uani 1 1 d . . . . .
H22 H 1.222366 0.351682 0.458143 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7352(2) 0.43799(5) 0.48266(3) 0.0282(2) Uani 1 1 d . . . . .
H23A H 0.756002 0.470564 0.504391 0.042 Uiso 1 1 calc R U . . .
H23B H 0.772290 0.390533 0.491392 0.042 Uiso 1 1 calc R U . . .
H23C H 0.569061 0.439902 0.473476 0.042 Uiso 1 1 calc R U . . .
C24 C 0.8468(2) 0.52975(5) 0.44029(3) 0.0315(2) Uani 1 1 d . . . . .
H24A H 0.849101 0.558857 0.463753 0.047 Uiso 1 1 calc R U . . .
H24B H 0.688764 0.532730 0.427972 0.047 Uiso 1 1 calc R U . . .
H24C H 0.969302 0.546212 0.422029 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.4748(12) . ?
N1 C23 1.4611(13) . ?
N1 C24 1.4621(12) . ?
C1 C2 1.3962(14) . ?
C1 C6 1.4148(13) . ?
C1 C15 1.5132(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3854(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3880(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3835(14) . ?
C6 C5 1.4047(14) . ?
C6 C7 1.4725(13) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.3375(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.4685(13) . ?
C9 C10 1.4002(13) . ?
C9 C14 1.4045(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3904(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3864(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3936(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3858(14) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5477(12) . ?
C16 H16 1.0000 . ?
C16 C17 1.5188(12) . ?
C17 C18 1.3892(13) . ?
C17 C22 1.3979(13) . ?
C18 H18 0.9500 . ?
C18 C19 1.3913(13) . ?
C19 H19 0.9500 . ?
C19 C20 1.3854(14) . ?
C20 H20 0.9500 . ?
C20 C21 1.3907(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.3887(13) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 N1 C16 109.74(7) . . ?
C23 N1 C24 108.07(8) . . ?
C24 N1 C16 111.78(8) . . ?
C2 C1 C6 118.99(9) . . ?
C2 C1 C15 119.03(8) . . ?
C6 C1 C15 121.92(8) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.79(9) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.35(9) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.96(9) . . ?
C5 C4 H4 120.0 . . ?
C1 C6 C7 121.10(9) . . ?
C5 C6 C1 118.33(9) . . ?
C5 C6 C7 120.57(9) . . ?
C4 C5 C6 121.57(9) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C6 C7 H7 116.7 . . ?
C8 C7 C6 126.62(9) . . ?
C8 C7 H7 116.7 . . ?
C7 C8 H8 116.9 . . ?
C7 C8 C9 126.14(9) . . ?
C9 C8 H8 116.9 . . ?
C10 C9 C8 119.09(9) . . ?
C10 C9 C14 117.68(9) . . ?
C14 C9 C8 123.18(9) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.30(10) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.23(9) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.30(9) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.51(9) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.96(9) . . ?
C13 C14 H14 119.5 . . ?
C1 C15 H15A 109.3 . . ?
C1 C15 H15B 109.3 . . ?
C1 C15 C16 111.56(7) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N1 C16 C15 111.98(7) . . ?
N1 C16 H16 108.3 . . ?
N1 C16 C17 110.85(7) . . ?
C15 C16 H16 108.3 . . ?
C17 C16 C15 109.12(7) . . ?
C17 C16 H16 108.3 . . ?
C18 C17 C16 120.61(8) . . ?
C18 C17 C22 118.56(8) . . ?
C22 C17 C16 120.78(8) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.84(9) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.13(9) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.73(9) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.93(9) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.81(9) . . ?
C21 C22 H22 119.6 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C16 C17 C18 134.22(9) . . . . ?
N1 C16 C17 C22 -48.39(11) . . . . ?
C1 C2 C3 C4 0.47(15) . . . . ?
C1 C6 C5 C4 0.28(14) . . . . ?
C1 C6 C7 C8 -176.16(9) . . . . ?
C1 C15 C16 N1 -172.21(7) . . . . ?
C1 C15 C16 C17 64.69(10) . . . . ?
C2 C1 C6 C5 0.63(13) . . . . ?
C2 C1 C6 C7 -179.33(8) . . . . ?
C2 C1 C15 C16 -97.56(10) . . . . ?
C2 C3 C4 C5 0.46(15) . . . . ?
C3 C4 C5 C6 -0.83(15) . . . . ?
C6 C1 C2 C3 -1.01(14) . . . . ?
C6 C1 C15 C16 79.68(11) . . . . ?
C6 C7 C8 C9 178.82(9) . . . . ?
C5 C6 C7 C8 3.89(15) . . . . ?
C7 C6 C5 C4 -179.77(9) . . . . ?
C7 C8 C9 C10 177.36(9) . . . . ?
C7 C8 C9 C14 -5.10(15) . . . . ?
C8 C9 C10 C11 176.54(9) . . . . ?
C8 C9 C14 C13 -175.86(9) . . . . ?
C9 C10 C11 C12 -0.32(16) . . . . ?
C10 C9 C14 C13 1.71(14) . . . . ?
C10 C11 C12 C13 1.22(15) . . . . ?
C11 C12 C13 C14 -0.65(15) . . . . ?
C12 C13 C14 C9 -0.85(15) . . . . ?
C14 C9 C10 C11 -1.13(14) . . . . ?
C15 C1 C2 C3 176.31(9) . . . . ?
C15 C1 C6 C5 -176.61(8) . . . . ?
C15 C1 C6 C7 3.44(13) . . . . ?
C15 C16 C17 C18 -102.01(10) . . . . ?
C15 C16 C17 C22 75.38(10) . . . . ?
C16 C17 C18 C19 177.03(9) . . . . ?
C16 C17 C22 C21 -177.63(9) . . . . ?
C17 C18 C19 C20 0.47(15) . . . . ?
C18 C17 C22 C21 -0.19(14) . . . . ?
C18 C19 C20 C21 0.09(15) . . . . ?
C19 C20 C21 C22 -0.70(15) . . . . ?
C20 C21 C22 C17 0.75(15) . . . . ?
C22 C17 C18 C19 -0.42(14) . . . . ?
C23 N1 C16 C15 179.43(8) . . . . ?
C23 N1 C16 C17 -58.46(10) . . . . ?
C24 N1 C16 C15 59.54(11) . . . . ?
C24 N1 C16 C17 -178.35(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_p492
_database_code_depnum_ccdc_archive 'CCDC 2222216'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-09-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N'
_chemical_formula_sum            'C27 H29 N'
_chemical_formula_weight         367.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C27H29N
_chemical_oxdiff_usercomment     P492
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   38.6981(3)
_cell_length_b                   5.37771(3)
_cell_length_c                   19.93774(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4149.18(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19669
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.6050
_cell_measurement_theta_min      2.2710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30001
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.782
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  24.00   0.50    1.36    --  -48.50   5.00 -62.00  118
  2  ω     37.00  97.00   0.50    1.36    --   48.50-129.00 -53.00  120
  3  ω    -96.00 -70.00   0.50    5.44    --  -86.25  -5.00 120.00   52
  4  ω     89.00 115.00   0.50    5.44    --  107.75-129.00  36.00   52
  5  ω     91.00 177.00   0.50    5.44    --  107.75   5.00 -62.00  172
  6  ω     51.00 115.00   0.50    5.44    --  107.75-129.00 -53.00  128
  7  ω    -25.00   1.00   0.50    1.36    --  -48.50  19.00-120.00   52
  8  ω    -25.00   1.00   0.50    1.36    --  -48.50  19.00 -30.00   52
  9  ω    -22.00  42.00   0.50    1.36    --   48.50 -38.00 -90.00  128
 10  ω     37.00  69.00   0.50    5.44    --  107.75 -61.00 -60.00   64
 11  ω    107.00 135.00   0.50    5.44    --  107.75  30.00 -60.00   56
 12  ω     57.00  83.00   0.50    5.44    --  107.75-112.00  36.17   52
 13  ω    105.00 131.00   0.50    5.44    --  107.75 118.00  87.86   52
 14  ω    150.00 176.00   0.50    5.44    --  107.75 118.00  65.93   52
 15  ω     79.00 104.00   0.50    5.44    --  107.75-117.00  58.60   50
 16  ω    147.00 178.00   0.50    5.44    --  107.75 118.00  87.86   62
 17  ω     49.00  75.00   0.50    5.44    --  107.75-109.00-136.09   52
 18  ω    153.00 178.00   0.50    5.44    --  107.75  30.00 -60.00   50
 19  ω     82.00 108.00   0.50    5.44    --  107.75-114.00 -64.35   52
 20  ω     98.00 173.00   0.50    5.44    --  107.75  45.00 150.00  150
 21  ω     98.00 130.00   0.50    5.44    --  107.75  30.00 120.00   64
 22  ω     84.00 109.00   0.50    5.44    --  107.75-112.00  36.17   50
 23  ω     39.00  67.00   0.50    5.44    --  107.75 -61.00 -30.00   56
 24  ω     37.00  72.00   0.50    5.44    --  107.75-117.00  58.60   70
 25  ω     58.00 109.00   0.50    5.44    --  107.75-117.00 123.70  102
 26  ω     86.00 111.00   0.50    5.44    --  107.75-125.00 -30.00   50
 27  ω     55.00  81.00   0.50    5.44    --  107.75 -77.00 -30.00   52
 28  ω     45.00  71.00   0.50    5.44    --  107.75-107.00 -35.01   52
 29  ω    102.00 143.00   0.50    5.44    --  107.75  45.00 120.00   82
 30  ω    120.00 146.00   0.50    5.44    --  107.75 114.00 -80.89   52
 31  ω     36.00  61.00   0.50    5.44    --  107.75 -61.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0114464000
_diffrn_orient_matrix_UB_12      -0.0154137000
_diffrn_orient_matrix_UB_13      0.0738762000
_diffrn_orient_matrix_UB_21      -0.0380841000
_diffrn_orient_matrix_UB_22      -0.0088104000
_diffrn_orient_matrix_UB_23      -0.0223714000
_diffrn_orient_matrix_UB_31      0.0017723000
_diffrn_orient_matrix_UB_32      -0.2859799000
_diffrn_orient_matrix_UB_33      -0.0032933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4144
_reflns_number_total             4389
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+1.3275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57129(2) 0.67833(15) 0.43078(4) 0.01979(17) Uani 1 1 d . . . . .
C1 C 0.66403(2) 0.72345(17) 0.49953(5) 0.02054(19) Uani 1 1 d . . . . .
C2 C 0.67098(2) 0.85249(18) 0.55871(5) 0.0235(2) Uani 1 1 d . . . . .
H2 H 0.656825 0.989989 0.570541 0.028 Uiso 1 1 calc R U . . .
C4 C 0.71884(3) 0.58582(19) 0.58343(5) 0.0245(2) Uani 1 1 d . . . . .
H4 H 0.737255 0.537253 0.612099 0.029 Uiso 1 1 calc R U . . .
C3 C 0.69794(3) 0.78578(19) 0.60069(5) 0.0251(2) Uani 1 1 d . . . . .
H3 H 0.702095 0.875854 0.640875 0.030 Uiso 1 1 calc R U . . .
C5 C 0.71282(2) 0.45746(18) 0.52445(5) 0.0232(2) Uani 1 1 d . . . . .
H5 H 0.727494 0.322586 0.512803 0.028 Uiso 1 1 calc R U . . .
C6 C 0.68554(2) 0.52174(17) 0.48140(5) 0.02042(19) Uani 1 1 d . . . . .
C7 C 0.67946(2) 0.38124(18) 0.41919(5) 0.02171(19) Uani 1 1 d . . . . .
H7 H 0.661171 0.437617 0.391283 0.026 Uiso 1 1 calc R U . . .
C8 C 0.69707(2) 0.18206(18) 0.39791(5) 0.0219(2) Uani 1 1 d . . . . .
H8 H 0.715789 0.127832 0.425043 0.026 Uiso 1 1 calc R U . . .
C9 C 0.69016(2) 0.03955(17) 0.33653(5) 0.02091(19) Uani 1 1 d . . . . .
C10 C 0.71188(3) -0.15929(18) 0.32000(5) 0.0249(2) Uani 1 1 d . . . . .
H10 H 0.731396 -0.193403 0.347416 0.030 Uiso 1 1 calc R U . . .
C11 C 0.70551(3) -0.30795(19) 0.26430(5) 0.0282(2) Uani 1 1 d . . . . .
H11 H 0.720677 -0.441395 0.253899 0.034 Uiso 1 1 calc R U . . .
C12 C 0.67706(3) -0.26177(19) 0.22394(5) 0.0274(2) Uani 1 1 d . . . . .
H12 H 0.672377 -0.365020 0.186358 0.033 Uiso 1 1 calc R U . . .
C13 C 0.65541(3) -0.06243(19) 0.23901(5) 0.0262(2) Uani 1 1 d . . . . .
H13 H 0.636067 -0.028421 0.211134 0.031 Uiso 1 1 calc R U . . .
C14 C 0.66185(3) 0.08649(18) 0.29426(5) 0.0236(2) Uani 1 1 d . . . . .
H14 H 0.646916 0.222261 0.303726 0.028 Uiso 1 1 calc R U . . .
C15 C 0.63277(2) 0.79591(17) 0.45820(5) 0.02084(19) Uani 1 1 d . . . . .
H15A H 0.638509 0.782592 0.409944 0.025 Uiso 1 1 calc R U . . .
H15B H 0.626678 0.971188 0.467716 0.025 Uiso 1 1 calc R U . . .
C16 C 0.60140(2) 0.62775(16) 0.47393(4) 0.01880(19) Uani 1 1 d . . . . .
H16 H 0.608457 0.450478 0.467488 0.023 Uiso 1 1 calc R U . . .
C17 C 0.59097(2) 0.66398(16) 0.54697(4) 0.01838(18) Uani 1 1 d . . . . .
C18 C 0.60152(2) 0.49912(18) 0.59662(5) 0.0229(2) Uani 1 1 d . . . . .
H18 H 0.614852 0.357467 0.584744 0.028 Uiso 1 1 calc R U . . .
C19 C 0.59282(3) 0.53884(19) 0.66349(5) 0.0264(2) Uani 1 1 d . . . . .
H19 H 0.600329 0.425040 0.696890 0.032 Uiso 1 1 calc R U . . .
C20 C 0.57323(3) 0.74373(19) 0.68147(5) 0.0252(2) Uani 1 1 d . . . . .
H20 H 0.567107 0.770194 0.727059 0.030 Uiso 1 1 calc R U . . .
C21 C 0.56262(3) 0.91020(18) 0.63242(5) 0.0248(2) Uani 1 1 d . . . . .
H21 H 0.549255 1.051439 0.644499 0.030 Uiso 1 1 calc R U . . .
C22 C 0.57147(2) 0.87103(17) 0.56569(5) 0.0217(2) Uani 1 1 d . . . . .
H22 H 0.564177 0.986331 0.532479 0.026 Uiso 1 1 calc R U . . .
C23 C 0.54531(3) 0.4836(2) 0.44174(5) 0.0255(2) Uani 1 1 d . . . . .
H23A H 0.541320 0.463250 0.490480 0.031 Uiso 1 1 calc R U . . .
H23B H 0.554086 0.323655 0.423975 0.031 Uiso 1 1 calc R U . . .
C24 C 0.51137(3) 0.5475(2) 0.40743(5) 0.0314(2) Uani 1 1 d . . . . .
H24A H 0.501883 0.702617 0.426812 0.038 Uiso 1 1 calc R U . . .
H24B H 0.494438 0.412525 0.415248 0.038 Uiso 1 1 calc R U . . .
C25 C 0.51690(3) 0.5812(2) 0.33238(5) 0.0287(2) Uani 1 1 d . . . . .
H25A H 0.495370 0.643157 0.311380 0.034 Uiso 1 1 calc R U . . .
H25B H 0.522765 0.419354 0.311659 0.034 Uiso 1 1 calc R U . . .
C26 C 0.54608(3) 0.7660(2) 0.32027(5) 0.0285(2) Uani 1 1 d . . . . .
H26A H 0.538436 0.933944 0.334173 0.034 Uiso 1 1 calc R U . . .
H26B H 0.551392 0.771707 0.271719 0.034 Uiso 1 1 calc R U . . .
C27 C 0.57873(3) 0.6965(2) 0.35892(5) 0.0250(2) Uani 1 1 d . . . . .
H27A H 0.587639 0.535128 0.342414 0.030 Uiso 1 1 calc R U . . .
H27B H 0.596738 0.824088 0.351267 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.4735(12) . ?
N1 C23 1.4682(12) . ?
N1 C27 1.4647(12) . ?
C1 C2 1.3951(14) . ?
C1 C6 1.4142(13) . ?
C1 C15 1.5145(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3848(14) . ?
C4 H4 0.9500 . ?
C4 C3 1.3889(14) . ?
C4 C5 1.3834(14) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.4039(13) . ?
C6 C7 1.4711(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.3386(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.4684(13) . ?
C9 C10 1.3995(13) . ?
C9 C14 1.4053(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3904(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.3861(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3935(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.3846(14) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5460(12) . ?
C16 H16 1.0000 . ?
C16 C17 1.5237(12) . ?
C17 C18 1.3901(13) . ?
C17 C22 1.3959(13) . ?
C18 H18 0.9500 . ?
C18 C19 1.3916(14) . ?
C19 H19 0.9500 . ?
C19 C20 1.3845(15) . ?
C20 H20 0.9500 . ?
C20 C21 1.3881(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.3899(13) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5205(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5225(14) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5233(15) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5264(14) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 N1 C16 108.83(7) . . ?
C27 N1 C16 115.35(7) . . ?
C27 N1 C23 109.12(7) . . ?
C2 C1 C6 118.96(9) . . ?
C2 C1 C15 119.09(8) . . ?
C6 C1 C15 121.89(8) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.84(9) . . ?
C3 C2 H2 119.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.92(9) . . ?
C2 C3 C4 119.32(9) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.58(9) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 121.02(8) . . ?
C5 C6 C1 118.37(9) . . ?
C5 C6 C7 120.61(8) . . ?
C6 C7 H7 116.7 . . ?
C8 C7 C6 126.65(9) . . ?
C8 C7 H7 116.7 . . ?
C7 C8 H8 117.0 . . ?
C7 C8 C9 126.10(9) . . ?
C9 C8 H8 117.0 . . ?
C10 C9 C8 119.06(9) . . ?
C10 C9 C14 117.67(9) . . ?
C14 C9 C8 123.23(9) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.39(9) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.11(9) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.36(9) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.55(10) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.90(9) . . ?
C13 C14 H14 119.5 . . ?
C1 C15 H15A 109.3 . . ?
C1 C15 H15B 109.3 . . ?
C1 C15 C16 111.49(7) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N1 C16 C15 113.23(7) . . ?
N1 C16 H16 108.5 . . ?
N1 C16 C17 108.97(7) . . ?
C15 C16 H16 108.5 . . ?
C17 C16 C15 109.09(7) . . ?
C17 C16 H16 108.5 . . ?
C18 C17 C16 121.42(8) . . ?
C18 C17 C22 118.50(9) . . ?
C22 C17 C16 120.04(8) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.88(9) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.18(9) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.52(9) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.26(9) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.66(9) . . ?
C21 C22 H22 119.7 . . ?
N1 C23 H23A 109.4 . . ?
N1 C23 H23B 109.4 . . ?
N1 C23 C24 111.31(8) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C23 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C23 C24 C25 110.35(8) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C24 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C24 C25 C26 109.74(8) . . ?
H25A C25 H25B 108.2 . . ?
C26 C25 H25A 109.7 . . ?
C26 C25 H25B 109.7 . . ?
C25 C26 H26A 109.2 . . ?
C25 C26 H26B 109.2 . . ?
C25 C26 C27 111.95(8) . . ?
H26A C26 H26B 107.9 . . ?
C27 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
N1 C27 C26 110.34(8) . . ?
N1 C27 H27A 109.6 . . ?
N1 C27 H27B 109.6 . . ?
C26 C27 H27A 109.6 . . ?
C26 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C16 C17 C18 137.62(9) . . . . ?
N1 C16 C17 C22 -44.75(11) . . . . ?
N1 C23 C24 C25 58.69(12) . . . . ?
C1 C2 C3 C4 0.37(15) . . . . ?
C1 C6 C7 C8 -177.28(9) . . . . ?
C1 C15 C16 N1 -175.20(7) . . . . ?
C1 C15 C16 C17 63.27(10) . . . . ?
C2 C1 C6 C5 0.89(13) . . . . ?
C2 C1 C6 C7 -179.45(8) . . . . ?
C2 C1 C15 C16 -96.55(10) . . . . ?
C4 C5 C6 C1 0.15(14) . . . . ?
C4 C5 C6 C7 -179.51(9) . . . . ?
C3 C4 C5 C6 -0.96(15) . . . . ?
C5 C4 C3 C2 0.69(14) . . . . ?
C5 C6 C7 C8 2.37(15) . . . . ?
C6 C1 C2 C3 -1.17(14) . . . . ?
C6 C1 C15 C16 80.67(10) . . . . ?
C6 C7 C8 C9 178.31(9) . . . . ?
C7 C8 C9 C10 177.59(9) . . . . ?
C7 C8 C9 C14 -4.89(15) . . . . ?
C8 C9 C10 C11 176.77(9) . . . . ?
C8 C9 C14 C13 -176.32(9) . . . . ?
C9 C10 C11 C12 -0.34(15) . . . . ?
C10 C9 C14 C13 1.24(14) . . . . ?
C10 C11 C12 C13 1.26(15) . . . . ?
C11 C12 C13 C14 -0.92(15) . . . . ?
C12 C13 C14 C9 -0.35(15) . . . . ?
C14 C9 C10 C11 -0.90(14) . . . . ?
C15 C1 C2 C3 176.13(9) . . . . ?
C15 C1 C6 C5 -176.33(8) . . . . ?
C15 C1 C6 C7 3.33(13) . . . . ?
C15 C16 C17 C18 -98.30(10) . . . . ?
C15 C16 C17 C22 79.33(10) . . . . ?
C16 N1 C23 C24 170.70(8) . . . . ?
C16 N1 C27 C26 -176.26(8) . . . . ?
C16 C17 C18 C19 177.80(9) . . . . ?
C16 C17 C22 C21 -178.15(9) . . . . ?
C17 C18 C19 C20 0.37(15) . . . . ?
C18 C17 C22 C21 -0.45(14) . . . . ?
C18 C19 C20 C21 -0.56(15) . . . . ?
C19 C20 C21 C22 0.24(15) . . . . ?
C20 C21 C22 C17 0.27(15) . . . . ?
C22 C17 C18 C19 0.13(14) . . . . ?
C23 N1 C16 C15 170.54(8) . . . . ?
C23 N1 C16 C17 -67.87(9) . . . . ?
C23 N1 C27 C26 60.90(10) . . . . ?
C23 C24 C25 C26 -52.34(12) . . . . ?
C24 C25 C26 C27 52.18(12) . . . . ?
C25 C26 C27 N1 -56.97(11) . . . . ?
C27 N1 C16 C15 47.55(11) . . . . ?
C27 N1 C16 C17 169.14(8) . . . . ?
C27 N1 C23 C24 -62.64(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.612
####################################################################### 
# 
# 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_P484
_database_code_depnum_ccdc_archive 'CCDC 2222214'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_P484                
;
PROBLEM: D-H Bond Without Acceptor  O1A      --H1A      .     Please Check 
RESPONSE: This is due to the unique chemical structure.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 O'
_chemical_formula_sum            'C30 H24 O'
_chemical_formula_weight         400.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.1904(2)
_cell_length_b                   8.1110(2)
_cell_length_c                   46.9573(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.9210(10)
_cell_angle_gamma                90
_cell_volume                     4252.12(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      31.80

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.682
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_power             50
_diffrn_source_current           30
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            136595
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -72
_diffrn_reflns_limit_l_max       71
_diffrn_reflns_theta_min         2.433
_diffrn_reflns_theta_max         33.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             15999
_reflns_number_gt                10996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+2.3740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15999
_refine_ls_number_parameters     567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.44403(9) 0.56088(12) 0.45944(2) 0.0225(2) Uani 1 1 d . . . . .
H1A H 0.388(2) 0.517(3) 0.4687(5) 0.056(7) Uiso 1 1 d . . . . .
O1B O 0.67351(9) 0.39754(12) 0.46831(2) 0.0253(2) Uani 1 1 d . . . . .
H1B H 0.608(2) 0.459(3) 0.4692(5) 0.062(7) Uiso 1 1 d . . . . .
C1A C 0.18681(11) 0.69323(16) 0.43807(3) 0.0196(2) Uani 1 1 d . . . . .
C1B C 0.44314(11) 0.16880(15) 0.46411(3) 0.0182(2) Uani 1 1 d . . . . .
C2A C 0.14917(12) 0.70509(17) 0.46566(3) 0.0232(3) Uani 1 1 d . . . . .
H2A H 0.200954 0.753178 0.480245 0.028 Uiso 1 1 calc R U . . .
C2B C 0.40222(12) 0.20710(16) 0.49075(3) 0.0215(2) Uani 1 1 d . . . . .
H2B H 0.456197 0.201482 0.507241 0.026 Uiso 1 1 calc R U . . .
C3A C 0.03720(13) 0.64788(18) 0.47228(3) 0.0263(3) Uani 1 1 d . . . . .
H3A H 0.012808 0.657719 0.491185 0.032 Uiso 1 1 calc R U . . .
C3B C 0.28393(13) 0.25333(17) 0.49361(3) 0.0241(3) Uani 1 1 d . . . . .
H3B H 0.257430 0.278623 0.511904 0.029 Uiso 1 1 calc R U . . .
C4A C -0.03882(12) 0.57635(18) 0.45116(3) 0.0259(3) Uani 1 1 d . . . . .
H4A H -0.115042 0.536017 0.455603 0.031 Uiso 1 1 calc R U . . .
C4B C 0.20472(12) 0.26226(17) 0.46951(3) 0.0234(3) Uani 1 1 d . . . . .
H4B H 0.124082 0.295151 0.471270 0.028 Uiso 1 1 calc R U . . .
C5A C -0.00291(12) 0.56407(17) 0.42353(3) 0.0236(3) Uani 1 1 d . . . . .
H5A H -0.055565 0.515682 0.409155 0.028 Uiso 1 1 calc R U . . .
C5B C 0.24340(11) 0.22322(16) 0.44295(3) 0.0204(2) Uani 1 1 d . . . . .
H5B H 0.188377 0.228465 0.426648 0.025 Uiso 1 1 calc R U . . .
C6A C 0.10976(11) 0.62167(16) 0.41632(3) 0.0204(2) Uani 1 1 d . . . . .
C6B C 0.36237(11) 0.17601(15) 0.43964(3) 0.0180(2) Uani 1 1 d . . . . .
C7A C 0.14560(12) 0.61655(17) 0.38684(3) 0.0224(3) Uani 1 1 d . . . . .
H7A H 0.217901 0.672448 0.383482 0.027 Uiso 1 1 calc R U . . .
C7B C 0.40316(11) 0.13342(15) 0.41150(3) 0.0187(2) Uani 1 1 d . . . . .
H7B H 0.474856 0.070790 0.411360 0.022 Uiso 1 1 calc R U . . .
C8A C 0.08990(12) 0.54357(17) 0.36406(3) 0.0236(3) Uani 1 1 d . . . . .
H8A H 0.021685 0.477902 0.367136 0.028 Uiso 1 1 calc R U . . .
C8B C 0.35000(11) 0.17349(16) 0.38598(3) 0.0196(2) Uani 1 1 d . . . . .
H8B H 0.279931 0.239744 0.385721 0.024 Uiso 1 1 calc R U . . .
C9A C 0.12608(12) 0.55717(17) 0.33469(3) 0.0230(3) Uani 1 1 d . . . . .
C9B C 0.39222(11) 0.12240(16) 0.35840(3) 0.0192(2) Uani 1 1 d . . . . .
C10A C 0.05751(12) 0.48246(17) 0.31268(3) 0.0239(3) Uani 1 1 d . . . . .
H10A H -0.012189 0.423232 0.317023 0.029 Uiso 1 1 calc R U . . .
C10B C 0.32656(12) 0.16289(17) 0.33352(3) 0.0213(2) Uani 1 1 d . . . . .
H10B H 0.256349 0.227897 0.334514 0.026 Uiso 1 1 calc R U . . .
C11A C 0.08766(12) 0.49124(17) 0.28389(3) 0.0245(3) Uani 1 1 d . . . . .
C11B C 0.36081(12) 0.11018(17) 0.30638(3) 0.0220(3) Uani 1 1 d . . . . .
C12A C 0.01906(14) 0.4117(2) 0.26129(3) 0.0309(3) Uani 1 1 d . . . . .
H12A H -0.052287 0.354904 0.265175 0.037 Uiso 1 1 calc R U . . .
C12B C 0.29079(14) 0.1447(2) 0.28083(3) 0.0335(3) Uani 1 1 d . . . . .
H12B H 0.218890 0.206418 0.281566 0.040 Uiso 1 1 calc R U . . .
C13A C 0.05470(15) 0.4159(2) 0.23397(4) 0.0358(4) Uani 1 1 d . . . . .
H13A H 0.008315 0.361355 0.219105 0.043 Uiso 1 1 calc R U . . .
C13B C 0.32556(16) 0.0902(2) 0.25506(3) 0.0399(4) Uani 1 1 d . . . . .
H13B H 0.278122 0.115550 0.238066 0.048 Uiso 1 1 calc R U . . .
C14A C 0.15976(15) 0.5007(2) 0.22776(3) 0.0354(4) Uani 1 1 d . . . . .
H14A H 0.184573 0.501287 0.208812 0.042 Uiso 1 1 calc R U . . .
C14B C 0.43128(15) -0.0032(2) 0.25355(3) 0.0346(4) Uani 1 1 d . . . . .
H14B H 0.454621 -0.040589 0.235577 0.042 Uiso 1 1 calc R U . . .
C15A C 0.22634(14) 0.5823(2) 0.24894(3) 0.0317(3) Uani 1 1 d . . . . .
H15A H 0.295868 0.641457 0.244460 0.038 Uiso 1 1 calc R U . . .
C15B C 0.50042(13) -0.04011(19) 0.27793(3) 0.0277(3) Uani 1 1 d . . . . .
H15B H 0.571156 -0.103802 0.276764 0.033 Uiso 1 1 calc R U . . .
C16A C 0.19235(13) 0.57905(18) 0.27745(3) 0.0258(3) Uani 1 1 d . . . . .
C16B C 0.46730(12) 0.01591(17) 0.30490(3) 0.0217(3) Uani 1 1 d . . . . .
C17A C 0.26111(13) 0.65769(19) 0.30010(3) 0.0278(3) Uani 1 1 d . . . . .
H17A H 0.330435 0.718556 0.296021 0.033 Uiso 1 1 calc R U . . .
C17B C 0.53577(12) -0.02151(18) 0.33064(3) 0.0251(3) Uani 1 1 d . . . . .
H17B H 0.608047 -0.082335 0.329923 0.030 Uiso 1 1 calc R U . . .
C18A C 0.22943(13) 0.64744(19) 0.32763(3) 0.0271(3) Uani 1 1 d . . . . .
H18A H 0.277076 0.701384 0.342340 0.033 Uiso 1 1 calc R U . . .
C18B C 0.49941(12) 0.02852(18) 0.35642(3) 0.0245(3) Uani 1 1 d . . . . .
H18B H 0.546237 0.000420 0.373360 0.029 Uiso 1 1 calc R U . . .
C19A C 0.31157(11) 0.74930(15) 0.43206(3) 0.0195(2) Uani 1 1 d . . . . .
H19A H 0.341996 0.826536 0.447190 0.023 Uiso 1 1 calc R U . . .
H19B H 0.308535 0.808716 0.413608 0.023 Uiso 1 1 calc R U . . .
C19B C 0.57398(11) 0.13151(16) 0.46138(3) 0.0204(2) Uani 1 1 d . . . . .
H19C H 0.581092 0.030573 0.449763 0.025 Uiso 1 1 calc R U . . .
H19D H 0.612918 0.109655 0.480576 0.025 Uiso 1 1 calc R U . . .
C20A C 0.39757(11) 0.60131(15) 0.43092(3) 0.0178(2) Uani 1 1 d . . . . .
H20A H 0.351408 0.504481 0.422863 0.021 Uiso 1 1 calc R U . . .
C20B C 0.63999(11) 0.27441(16) 0.44741(3) 0.0195(2) Uani 1 1 d . . . . .
H20B H 0.583961 0.325561 0.432422 0.023 Uiso 1 1 calc R U . . .
C21A C 0.50209(11) 0.63167(15) 0.41296(3) 0.0173(2) Uani 1 1 d . . . . .
C21B C 0.74914(11) 0.21375(16) 0.43337(3) 0.0199(2) Uani 1 1 d . . . . .
C22A C 0.49951(11) 0.56963(16) 0.38570(3) 0.0186(2) Uani 1 1 d . . . . .
H22A H 0.431931 0.507727 0.378531 0.022 Uiso 1 1 calc R U . . .
C22B C 0.75412(11) 0.22834(16) 0.40441(3) 0.0213(2) Uani 1 1 d . . . . .
H22B H 0.691012 0.283325 0.393688 0.026 Uiso 1 1 calc R U . . .
C23A C 0.59549(11) 0.59600(16) 0.36804(3) 0.0192(2) Uani 1 1 d . . . . .
C23B C 0.85143(11) 0.16321(16) 0.38998(3) 0.0206(2) Uani 1 1 d . . . . .
C24A C 0.59581(13) 0.52670(19) 0.34031(3) 0.0262(3) Uani 1 1 d . . . . .
H24A H 0.530189 0.461221 0.333078 0.031 Uiso 1 1 calc R U . . .
C24B C 0.85717(13) 0.17542(18) 0.35998(3) 0.0256(3) Uani 1 1 d . . . . .
H24B H 0.794734 0.229605 0.348894 0.031 Uiso 1 1 calc R U . . .
C25A C 0.69079(14) 0.5541(2) 0.32393(3) 0.0303(3) Uani 1 1 d . . . . .
H25A H 0.690931 0.506063 0.305478 0.036 Uiso 1 1 calc R U . . .
C25B C 0.95206(13) 0.10970(18) 0.34679(3) 0.0275(3) Uani 1 1 d . . . . .
H25B H 0.954525 0.118103 0.326665 0.033 Uiso 1 1 calc R U . . .
C26A C 0.78815(13) 0.6528(2) 0.33416(3) 0.0293(3) Uani 1 1 d . . . . .
H26A H 0.852075 0.673364 0.322330 0.035 Uiso 1 1 calc R U . . .
C26B C 1.04603(13) 0.02968(17) 0.36297(3) 0.0261(3) Uani 1 1 d . . . . .
H26B H 1.111507 -0.015165 0.353689 0.031 Uiso 1 1 calc R U . . .
C27A C 0.79139(12) 0.71923(18) 0.36102(3) 0.0247(3) Uani 1 1 d . . . . .
H27A H 0.857874 0.784473 0.367799 0.030 Uiso 1 1 calc R U . . .
C27B C 1.04302(12) 0.01656(17) 0.39199(3) 0.0238(3) Uani 1 1 d . . . . .
H27B H 1.106675 -0.037369 0.402694 0.029 Uiso 1 1 calc R U . . .
C28A C 0.69565(11) 0.69088(16) 0.37877(3) 0.0193(2) Uani 1 1 d . . . . .
C28B C 0.94606(11) 0.08248(16) 0.40627(3) 0.0203(2) Uani 1 1 d . . . . .
C29A C 0.69680(11) 0.75324(16) 0.40705(3) 0.0203(2) Uani 1 1 d . . . . .
H29A H 0.763235 0.816445 0.414507 0.024 Uiso 1 1 calc R U . . .
C29B C 0.93933(12) 0.06844(17) 0.43629(3) 0.0222(3) Uani 1 1 d . . . . .
H29B H 1.001691 0.014038 0.447363 0.027 Uiso 1 1 calc R U . . .
C30A C 0.60326(11) 0.72338(15) 0.42372(3) 0.0189(2) Uani 1 1 d . . . . .
H30A H 0.606222 0.764582 0.442694 0.023 Uiso 1 1 calc R U . . .
C30B C 0.84408(12) 0.13235(17) 0.44947(3) 0.0224(3) Uani 1 1 d . . . . .
H30B H 0.841383 0.122220 0.469575 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C20A 1.4410(16) . ?
O1A H1A 0.86(2) . ?
O1B C20B 1.4323(16) . ?
O1B H1B 0.89(2) . ?
C1A C2A 1.3928(18) . ?
C1A C6A 1.4151(19) . ?
C1A C19A 1.5132(17) . ?
C1B C2B 1.3961(18) . ?
C1B C6B 1.4138(18) . ?
C1B C19B 1.5091(18) . ?
C2A C3A 1.3910(19) . ?
C2A H2A 0.9500 . ?
C2B C3B 1.3911(19) . ?
C2B H2B 0.9500 . ?
C3A C4A 1.389(2) . ?
C3A H3A 0.9500 . ?
C3B C4B 1.391(2) . ?
C3B H3B 0.9500 . ?
C4A C5A 1.388(2) . ?
C4A H4A 0.9500 . ?
C4B C5B 1.3845(18) . ?
C4B H4B 0.9500 . ?
C5A C6A 1.4074(18) . ?
C5A H5A 0.9500 . ?
C5B C6B 1.4041(18) . ?
C5B H5B 0.9500 . ?
C6A C7A 1.4681(19) . ?
C6B C7B 1.4685(17) . ?
C7A C8A 1.3387(19) . ?
C7A H7A 0.9500 . ?
C7B C8B 1.3411(18) . ?
C7B H7B 0.9500 . ?
C8A C9A 1.4677(19) . ?
C8A H8A 0.9500 . ?
C8B C9B 1.4681(18) . ?
C8B H8B 0.9500 . ?
C9A C10A 1.3840(19) . ?
C9A C18A 1.4269(19) . ?
C9B C10B 1.3768(18) . ?
C9B C18B 1.4292(18) . ?
C10A C11A 1.418(2) . ?
C10A H10A 0.9500 . ?
C10B C11B 1.4215(18) . ?
C10B H10B 0.9500 . ?
C11A C16A 1.421(2) . ?
C11A C12A 1.422(2) . ?
C11B C12B 1.415(2) . ?
C11B C16B 1.4216(18) . ?
C12A C13A 1.370(2) . ?
C12A H12A 0.9500 . ?
C12B C13B 1.370(2) . ?
C12B H12B 0.9500 . ?
C13A C14A 1.410(2) . ?
C13A H13A 0.9500 . ?
C13B C14B 1.411(2) . ?
C13B H13B 0.9500 . ?
C14A C15A 1.372(2) . ?
C14A H14A 0.9500 . ?
C14B C15B 1.371(2) . ?
C14B H14B 0.9500 . ?
C15A C16A 1.417(2) . ?
C15A H15A 0.9500 . ?
C15B C16B 1.4183(19) . ?
C15B H15B 0.9500 . ?
C16A C17A 1.421(2) . ?
C16B C17B 1.4190(19) . ?
C17A C18A 1.366(2) . ?
C17A H17A 0.9500 . ?
C17B C18B 1.3646(19) . ?
C17B H17B 0.9500 . ?
C18A H18A 0.9500 . ?
C18B H18B 0.9500 . ?
C19A C20A 1.5417(17) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C19B C20B 1.5447(18) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20A C21A 1.5081(17) . ?
C20A H20A 1.0000 . ?
C20B C21B 1.5094(18) . ?
C20B H20B 1.0000 . ?
C21A C22A 1.3740(18) . ?
C21A C30A 1.4185(17) . ?
C21B C22B 1.3699(19) . ?
C21B C30B 1.4237(18) . ?
C22A C23A 1.4174(17) . ?
C22A H22A 0.9500 . ?
C22B C23B 1.4229(18) . ?
C22B H22B 0.9500 . ?
C23A C24A 1.4182(19) . ?
C23A C28A 1.4230(18) . ?
C23B C24B 1.4182(19) . ?
C23B C28B 1.4228(18) . ?
C24A C25A 1.372(2) . ?
C24A H24A 0.9500 . ?
C24B C25B 1.373(2) . ?
C24B H24B 0.9500 . ?
C25A C26A 1.410(2) . ?
C25A H25A 0.9500 . ?
C25B C26B 1.412(2) . ?
C25B H25B 0.9500 . ?
C26A C27A 1.370(2) . ?
C26A H26A 0.9500 . ?
C26B C27B 1.370(2) . ?
C26B H26B 0.9500 . ?
C27A C28A 1.4203(18) . ?
C27A H27A 0.9500 . ?
C27B C28B 1.4185(18) . ?
C27B H27B 0.9500 . ?
C28A C29A 1.4205(19) . ?
C28B C29B 1.4213(19) . ?
C29A C30A 1.3709(17) . ?
C29A H29A 0.9500 . ?
C29B C30B 1.3705(18) . ?
C29B H29B 0.9500 . ?
C30A H30A 0.9500 . ?
C30B H30B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20A O1A H1A 109.5(15) . . ?
C20B O1B H1B 104.4(15) . . ?
C2A C1A C6A 119.44(12) . . ?
C2A C1A C19A 119.63(12) . . ?
C6A C1A C19A 120.86(11) . . ?
C2B C1B C6B 119.24(12) . . ?
C2B C1B C19B 120.02(12) . . ?
C6B C1B C19B 120.61(11) . . ?
C3A C2A C1A 121.26(13) . . ?
C3A C2A H2A 119.4 . . ?
C1A C2A H2A 119.4 . . ?
C3B C2B C1B 121.27(13) . . ?
C3B C2B H2B 119.4 . . ?
C1B C2B H2B 119.4 . . ?
C4A C3A C2A 119.82(13) . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A H3A 120.1 . . ?
C4B C3B C2B 119.54(12) . . ?
C4B C3B H3B 120.2 . . ?
C2B C3B H3B 120.2 . . ?
C5A C4A C3A 119.68(13) . . ?
C5A C4A H4A 120.2 . . ?
C3A C4A H4A 120.2 . . ?
C5B C4B C3B 120.00(12) . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4A C5A C6A 121.49(13) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C4B C5B C6B 121.28(13) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B H5B 119.4 . . ?
C5A C6A C1A 118.31(12) . . ?
C5A C6A C7A 121.62(12) . . ?
C1A C6A C7A 120.00(11) . . ?
C5B C6B C1B 118.66(11) . . ?
C5B C6B C7B 121.27(12) . . ?
C1B C6B C7B 120.06(11) . . ?
C8A C7A C6A 128.60(13) . . ?
C8A C7A H7A 115.7 . . ?
C6A C7A H7A 115.7 . . ?
C8B C7B C6B 126.94(12) . . ?
C8B C7B H7B 116.5 . . ?
C6B C7B H7B 116.5 . . ?
C7A C8A C9A 125.06(13) . . ?
C7A C8A H8A 117.5 . . ?
C9A C8A H8A 117.5 . . ?
C7B C8B C9B 124.75(12) . . ?
C7B C8B H8B 117.6 . . ?
C9B C8B H8B 117.6 . . ?
C10A C9A C18A 117.91(13) . . ?
C10A C9A C8A 119.62(12) . . ?
C18A C9A C8A 122.47(13) . . ?
C10B C9B C18B 118.26(12) . . ?
C10B C9B C8B 119.73(12) . . ?
C18B C9B C8B 122.00(12) . . ?
C9A C10A C11A 122.30(13) . . ?
C9A C10A H10A 118.9 . . ?
C11A C10A H10A 118.9 . . ?
C9B C10B C11B 121.88(12) . . ?
C9B C10B H10B 119.1 . . ?
C11B C10B H10B 119.1 . . ?
C10A C11A C16A 118.79(13) . . ?
C10A C11A C12A 122.53(13) . . ?
C16A C11A C12A 118.66(13) . . ?
C12B C11B C10B 122.19(12) . . ?
C12B C11B C16B 118.86(12) . . ?
C10B C11B C16B 118.93(12) . . ?
C13A C12A C11A 120.72(15) . . ?
C13A C12A H12A 119.6 . . ?
C11A C12A H12A 119.6 . . ?
C13B C12B C11B 120.71(14) . . ?
C13B C12B H12B 119.6 . . ?
C11B C12B H12B 119.6 . . ?
C12A C13A C14A 120.42(15) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C12B C13B C14B 120.50(15) . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B H13B 119.7 . . ?
C15A C14A C13A 120.32(15) . . ?
C15A C14A H14A 119.8 . . ?
C13A C14A H14A 119.8 . . ?
C15B C14B C13B 120.19(14) . . ?
C15B C14B H14B 119.9 . . ?
C13B C14B H14B 119.9 . . ?
C14A C15A C16A 120.58(15) . . ?
C14A C15A H15A 119.7 . . ?
C16A C15A H15A 119.7 . . ?
C14B C15B C16B 120.59(14) . . ?
C14B C15B H15B 119.7 . . ?
C16B C15B H15B 119.7 . . ?
C15A C16A C17A 122.17(14) . . ?
C15A C16A C11A 119.27(14) . . ?
C17A C16A C11A 118.55(13) . . ?
C15B C16B C17B 122.22(12) . . ?
C15B C16B C11B 119.13(13) . . ?
C17B C16B C11B 118.64(12) . . ?
C18A C17A C16A 121.25(13) . . ?
C18A C17A H17A 119.4 . . ?
C16A C17A H17A 119.4 . . ?
C18B C17B C16B 121.03(12) . . ?
C18B C17B H17B 119.5 . . ?
C16B C17B H17B 119.5 . . ?
C17A C18A C9A 121.19(13) . . ?
C17A C18A H18A 119.4 . . ?
C9A C18A H18A 119.4 . . ?
C17B C18B C9B 121.24(13) . . ?
C17B C18B H18B 119.4 . . ?
C9B C18B H18B 119.4 . . ?
C1A C19A C20A 111.01(10) . . ?
C1A C19A H19A 109.4 . . ?
C20A C19A H19A 109.4 . . ?
C1A C19A H19B 109.4 . . ?
C20A C19A H19B 109.4 . . ?
H19A C19A H19B 108.0 . . ?
C1B C19B C20B 112.38(10) . . ?
C1B C19B H19C 109.1 . . ?
C20B C19B H19C 109.1 . . ?
C1B C19B H19D 109.1 . . ?
C20B C19B H19D 109.1 . . ?
H19C C19B H19D 107.9 . . ?
O1A C20A C21A 108.21(10) . . ?
O1A C20A C19A 109.35(10) . . ?
C21A C20A C19A 113.71(10) . . ?
O1A C20A H20A 108.5 . . ?
C21A C20A H20A 108.5 . . ?
C19A C20A H20A 108.5 . . ?
O1B C20B C21B 110.17(10) . . ?
O1B C20B C19B 110.03(11) . . ?
C21B C20B C19B 111.45(10) . . ?
O1B C20B H20B 108.4 . . ?
C21B C20B H20B 108.4 . . ?
C19B C20B H20B 108.4 . . ?
C22A C21A C30A 119.29(11) . . ?
C22A C21A C20A 119.57(11) . . ?
C30A C21A C20A 121.14(11) . . ?
C22B C21B C30B 119.20(12) . . ?
C22B C21B C20B 119.63(12) . . ?
C30B C21B C20B 121.06(12) . . ?
C21A C22A C23A 121.43(12) . . ?
C21A C22A H22A 119.3 . . ?
C23A C22A H22A 119.3 . . ?
C21B C22B C23B 121.67(12) . . ?
C21B C22B H22B 119.2 . . ?
C23B C22B H22B 119.2 . . ?
C22A C23A C24A 121.79(12) . . ?
C22A C23A C28A 118.97(12) . . ?
C24A C23A C28A 119.21(12) . . ?
C24B C23B C28B 118.92(12) . . ?
C24B C23B C22B 122.36(12) . . ?
C28B C23B C22B 118.72(12) . . ?
C25A C24A C23A 120.07(14) . . ?
C25A C24A H24A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C25B C24B C23B 120.65(13) . . ?
C25B C24B H24B 119.7 . . ?
C23B C24B H24B 119.7 . . ?
C24A C25A C26A 120.74(14) . . ?
C24A C25A H25A 119.6 . . ?
C26A C25A H25A 119.6 . . ?
C24B C25B C26B 120.43(14) . . ?
C24B C25B H25B 119.8 . . ?
C26B C25B H25B 119.8 . . ?
C27A C26A C25A 120.56(13) . . ?
C27A C26A H26A 119.7 . . ?
C25A C26A H26A 119.7 . . ?
C27B C26B C25B 120.17(13) . . ?
C27B C26B H26B 119.9 . . ?
C25B C26B H26B 119.9 . . ?
C26A C27A C28A 120.20(14) . . ?
C26A C27A H27A 119.9 . . ?
C28A C27A H27A 119.9 . . ?
C26B C27B C28B 120.85(13) . . ?
C26B C27B H27B 119.6 . . ?
C28B C27B H27B 119.6 . . ?
C27A C28A C29A 122.14(12) . . ?
C27A C28A C23A 119.16(12) . . ?
C29A C28A C23A 118.70(11) . . ?
C27B C28B C29B 122.19(12) . . ?
C27B C28B C23B 118.98(13) . . ?
C29B C28B C23B 118.82(12) . . ?
C30A C29A C28A 120.83(12) . . ?
C30A C29A H29A 119.6 . . ?
C28A C29A H29A 119.6 . . ?
C30B C29B C28B 120.88(12) . . ?
C30B C29B H29B 119.6 . . ?
C28B C29B H29B 119.6 . . ?
C29A C30A C21A 120.75(12) . . ?
C29A C30A H30A 119.6 . . ?
C21A C30A H30A 119.6 . . ?
C29B C30B C21B 120.71(13) . . ?
C29B C30B H30B 119.6 . . ?
C21B C30B H30B 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 0.0(2) . . . . ?
C19A C1A C2A C3A -177.03(12) . . . . ?
C6B C1B C2B C3B -0.49(19) . . . . ?
C19B C1B C2B C3B 175.40(12) . . . . ?
C1A C2A C3A C4A 0.5(2) . . . . ?
C1B C2B C3B C4B -0.2(2) . . . . ?
C2A C3A C4A C5A -0.7(2) . . . . ?
C2B C3B C4B C5B 0.8(2) . . . . ?
C3A C4A C5A C6A 0.4(2) . . . . ?
C3B C4B C5B C6B -0.7(2) . . . . ?
C4A C5A C6A C1A 0.0(2) . . . . ?
C4A C5A C6A C7A -176.84(13) . . . . ?
C2A C1A C6A C5A -0.26(19) . . . . ?
C19A C1A C6A C5A 176.76(12) . . . . ?
C2A C1A C6A C7A 176.67(12) . . . . ?
C19A C1A C6A C7A -6.32(19) . . . . ?
C4B C5B C6B C1B 0.01(19) . . . . ?
C4B C5B C6B C7B 179.54(12) . . . . ?
C2B C1B C6B C5B 0.59(18) . . . . ?
C19B C1B C6B C5B -175.28(11) . . . . ?
C2B C1B C6B C7B -178.94(11) . . . . ?
C19B C1B C6B C7B 5.18(18) . . . . ?
C5A C6A C7A C8A -8.9(2) . . . . ?
C1A C6A C7A C8A 174.30(14) . . . . ?
C5B C6B C7B C8B 19.2(2) . . . . ?
C1B C6B C7B C8B -161.31(13) . . . . ?
C6A C7A C8A C9A 174.05(13) . . . . ?
C6B C7B C8B C9B -177.60(12) . . . . ?
C7A C8A C9A C10A -176.74(14) . . . . ?
C7A C8A C9A C18A 2.3(2) . . . . ?
C7B C8B C9B C10B 176.25(13) . . . . ?
C7B C8B C9B C18B -2.7(2) . . . . ?
C18A C9A C10A C11A 0.9(2) . . . . ?
C8A C9A C10A C11A 179.95(13) . . . . ?
C18B C9B C10B C11B 1.8(2) . . . . ?
C8B C9B C10B C11B -177.20(12) . . . . ?
C9A C10A C11A C16A 0.4(2) . . . . ?
C9A C10A C11A C12A 178.55(14) . . . . ?
C9B C10B C11B C12B 176.97(14) . . . . ?
C9B C10B C11B C16B -1.3(2) . . . . ?
C10A C11A C12A C13A -176.54(15) . . . . ?
C16A C11A C12A C13A 1.6(2) . . . . ?
C10B C11B C12B C13B -179.12(16) . . . . ?
C16B C11B C12B C13B -0.8(2) . . . . ?
C11A C12A C13A C14A -0.5(3) . . . . ?
C11B C12B C13B C14B 0.8(3) . . . . ?
C12A C13A C14A C15A -1.1(3) . . . . ?
C12B C13B C14B C15B -0.1(3) . . . . ?
C13A C14A C15A C16A 1.6(3) . . . . ?
C13B C14B C15B C16B -0.5(3) . . . . ?
C14A C15A C16A C17A 177.97(15) . . . . ?
C14A C15A C16A C11A -0.5(2) . . . . ?
C10A C11A C16A C15A 177.13(13) . . . . ?
C12A C11A C16A C15A -1.1(2) . . . . ?
C10A C11A C16A C17A -1.4(2) . . . . ?
C12A C11A C16A C17A -179.65(14) . . . . ?
C14B C15B C16B C17B 179.22(15) . . . . ?
C14B C15B C16B C11B 0.4(2) . . . . ?
C12B C11B C16B C15B 0.2(2) . . . . ?
C10B C11B C16B C15B 178.60(13) . . . . ?
C12B C11B C16B C17B -178.62(14) . . . . ?
C10B C11B C16B C17B -0.3(2) . . . . ?
C15A C16A C17A C18A -177.28(15) . . . . ?
C11A C16A C17A C18A 1.2(2) . . . . ?
C15B C16B C17B C18B -177.43(14) . . . . ?
C11B C16B C17B C18B 1.4(2) . . . . ?
C16A C17A C18A C9A 0.1(2) . . . . ?
C10A C9A C18A C17A -1.1(2) . . . . ?
C8A C9A C18A C17A 179.85(14) . . . . ?
C16B C17B C18B C9B -1.0(2) . . . . ?
C10B C9B C18B C17B -0.6(2) . . . . ?
C8B C9B C18B C17B 178.32(13) . . . . ?
C2A C1A C19A C20A 99.80(14) . . . . ?
C6A C1A C19A C20A -77.21(15) . . . . ?
C2B C1B C19B C20B -105.86(14) . . . . ?
C6B C1B C19B C20B 69.98(15) . . . . ?
C1A C19A C20A O1A -84.67(13) . . . . ?
C1A C19A C20A C21A 154.26(11) . . . . ?
C1B C19B C20B O1B 82.17(13) . . . . ?
C1B C19B C20B C21B -155.31(11) . . . . ?
O1A C20A C21A C22A 137.76(12) . . . . ?
C19A C20A C21A C22A -100.54(14) . . . . ?
O1A C20A C21A C30A -42.26(15) . . . . ?
C19A C20A C21A C30A 79.44(15) . . . . ?
O1B C20B C21B C22B -121.23(13) . . . . ?
C19B C20B C21B C22B 116.33(13) . . . . ?
O1B C20B C21B C30B 62.64(16) . . . . ?
C19B C20B C21B C30B -59.80(16) . . . . ?
C30A C21A C22A C23A -0.32(19) . . . . ?
C20A C21A C22A C23A 179.65(11) . . . . ?
C30B C21B C22B C23B 0.4(2) . . . . ?
C20B C21B C22B C23B -175.77(12) . . . . ?
C21A C22A C23A C24A 177.34(13) . . . . ?
C21A C22A C23A C28A -0.91(19) . . . . ?
C21B C22B C23B C24B 179.17(13) . . . . ?
C21B C22B C23B C28B -0.60(19) . . . . ?
C22A C23A C24A C25A -179.55(13) . . . . ?
C28A C23A C24A C25A -1.3(2) . . . . ?
C28B C23B C24B C25B 0.4(2) . . . . ?
C22B C23B C24B C25B -179.41(13) . . . . ?
C23A C24A C25A C26A -0.9(2) . . . . ?
C23B C24B C25B C26B -0.4(2) . . . . ?
C24A C25A C26A C27A 1.9(2) . . . . ?
C24B C25B C26B C27B 0.2(2) . . . . ?
C25A C26A C27A C28A -0.7(2) . . . . ?
C25B C26B C27B C28B 0.1(2) . . . . ?
C26A C27A C28A C29A 178.12(13) . . . . ?
C26A C27A C28A C23A -1.4(2) . . . . ?
C22A C23A C28A C27A -179.27(12) . . . . ?
C24A C23A C28A C27A 2.44(19) . . . . ?
C22A C23A C28A C29A 1.17(18) . . . . ?
C24A C23A C28A C29A -177.12(12) . . . . ?
C26B C27B C28B C29B 178.92(13) . . . . ?
C26B C27B C28B C23B -0.1(2) . . . . ?
C24B C23B C28B C27B -0.09(19) . . . . ?
C22B C23B C28B C27B 179.68(12) . . . . ?
C24B C23B C28B C29B -179.16(12) . . . . ?
C22B C23B C28B C29B 0.61(19) . . . . ?
C27A C28A C29A C30A -179.77(12) . . . . ?
C23A C28A C29A C30A -0.22(19) . . . . ?
C27B C28B C29B C30B -179.52(13) . . . . ?
C23B C28B C29B C30B -0.5(2) . . . . ?
C28A C29A C30A C21A -1.03(19) . . . . ?
C22A C21A C30A C29A 1.31(19) . . . . ?
C20A C21A C30A C29A -178.67(12) . . . . ?
C28B C29B C30B C21B 0.3(2) . . . . ?
C22B C21B C30B C29B -0.3(2) . . . . ?
C20B C21B C30B C29B 175.86(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1B H1B O1A 0.89(2) 2.04(2) 2.8943(14) 161(2) . yes

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.056

