# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_sg13
_database_code_depnum_ccdc_archive 'CCDC 2351176'
loop_
_audit_author_name
_audit_author_address
'Stanislav Groysman'
;Wayne State University
United States of America
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT082_sg13                
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: The high R1 value is a consequence of the low quality of
the diffraction data at higher angles used for structural determination due to
the weakly diffracting crystal.

;
_vrf_PLAT084_sg13                
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.43 Report
RESPONSE: The high wR2 value is a consequence of the low quality of
the diffraction data at higher angles used for structural determination due to
the weakly diffracting crystal.

;
_vrf_PLAT097_sg13                
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       4.24 eA-3  
RESPONSE: The extra density peak near C45 must be a result of the degradation 
of the crystal and/or twinning. The peak makes no chemical sense to be a 
missed assigned atom. 
;
_vrf_PLAT341_sg13                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01676 Ang.  
RESPONSE: The low bond precision is a consequence of the low quality of
the diffraction data at higher angles used for structural determination due to
the weakly diffracting crystal.

;
# end Validation Reply Form
_audit_creation_date             2024-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C52 H76 Fe N2 O2'
_chemical_formula_sum            'C52 H76 Fe N2 O2'
_chemical_formula_weight         816.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5346(8)
_cell_length_b                   13.1604(12)
_cell_length_c                   18.8315(15)
_cell_angle_alpha                91.840(3)
_cell_angle_beta                 90.463(3)
_cell_angle_gamma                91.367(3)
_cell_volume                     2361.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5006
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.290
_cell_measurement_theta_min      2.166
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.745209
_exptl_absorpt_correction_T_min  0.574295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1144 before and 0.0945 after correction.
 
For component 2:
 wR2(int) was 0.1156 before and 0.0963 after correction.
 The Ratio of minimum to maximum transmission is 0.77.

Final HKLF 4 output contains 81250 reflections, Rint = 0.1412
 (17444 with I > 3sig(I), Rint = 0.0821)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1412
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27533
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.363
_diffrn_reflns_theta_min         1.918
_diffrn_ambient_temperature      100
_diffrn_detector                 'Photon III'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.8 mm pinhole collimator'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                17586
_reflns_number_total             27533
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         4.245
_refine_diff_density_min         -1.286
_refine_diff_density_rms         0.252
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.435
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         27533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2119
_refine_ls_R_factor_gt           0.1598
_refine_ls_restrained_S_all      1.435
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3966
_refine_ls_wR_factor_ref         0.4283
_refine_special_details          
;
 Refined as a 2-component twin.

The crystal was determined to be a two-component non-merohedral 
twin related to each other by a 180° rotation around the 
reciprocal [0 0 1] rotation vector. Refinement was performed 
using the HKLF-5 using reflections from both domains, which lead 
to batch scale factor (BASF) parameter of 0.469(3). The crystal 
diffraction was very weak. Many attempts to recrystallize in 
different solvents did not lead to better diffraction quality. 
Cu radiation was also tried and did not result in a better 
structure result. The crystals were very fragile and sensitive. 
They degraded very quickly despite using paratone oil and quick 
transportation to the diffractometer. The extra density peak near 
C45 must be a result of the degradation and/or twinning. The peak 
makes no chemical sense. The compound has been characterized by 
several other methods.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.531(3)
 0.469(3)
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:
 C20(H20), C7(H7), C10(H10), C5(H5), C17(H17), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C19(H19A,H19B), C9(H9A,H9B), C14(H14A,H14B),
 C21(H21A,H21B), C8(H8A,H8B), C4(H4A,H4B), C22(H22A,H22B), C11(H11A,H11B),
 C18(H18A,H18B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C51(H51), C50(H50), C33(H33), C37(H37), C36(H36), C52(H52), C35(H35),
 C34(H34), C49(H49), C48(H48)
3.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C29(H29A,H29B,H29C), C26(H26A,H26B,H26C), C25(H25A,H25B,
 H25C), C30(H30A,H30B,H30C), C41(H41A,H41B,H41C), C31(H31A,H31B,H31C), C40(H40A,
 H40B,H40C), C44(H44A,H44B,H44C), C27(H27A,H27B,H27C), C45(H45A,H45B,H45C),
 C46(H46A,H46B,H46C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.38473(14) 0.76582(12) 0.74930(8) 0.0313(5) Uani 1 1 d . . . . .
O1 O 0.4923(8) 0.8805(6) 0.7544(5) 0.049(2) Uani 1 1 d . . . . .
O2 O 0.4229(9) 0.6363(7) 0.7381(4) 0.057(2) Uani 1 1 d . . . . .
C51 C 0.0522(12) 0.4721(9) 0.7533(6) 0.046(3) Uani 1 1 d . . . . .
H51 H -0.031463 0.509737 0.756045 0.056 Uiso 1 1 calc R U . . .
N1 N 0.1687(9) 0.7722(6) 0.6158(4) 0.037(2) Uani 1 1 d . . . . .
C50 C 0.0500(13) 0.3651(9) 0.7564(6) 0.047(3) Uani 1 1 d . . . . .
H50 H -0.036949 0.329149 0.760515 0.057 Uiso 1 1 calc R U . . .
C33 C 0.8286(10) 1.0331(9) 0.7516(7) 0.043(3) Uani 1 1 d . . . . .
H33 H 0.799732 1.101718 0.751451 0.052 Uiso 1 1 calc R U . . .
C37 C 0.7771(12) 0.8580(8) 0.7490(5) 0.039(3) Uani 1 1 d . . . . .
H37 H 0.711457 0.802512 0.746996 0.047 Uiso 1 1 calc R U . . .
C36 C 0.9168(13) 0.8380(9) 0.7511(6) 0.049(3) Uani 1 1 d . . . . .
H36 H 0.947780 0.770030 0.752102 0.059 Uiso 1 1 calc R U . . .
C52 C 0.1837(10) 0.5200(8) 0.7460(6) 0.038(2) Uani 1 1 d . . . . .
H52 H 0.188718 0.591727 0.741918 0.045 Uiso 1 1 calc R U . . .
C32 C 0.7268(11) 0.9569(8) 0.7498(6) 0.040(2) Uani 1 1 d . . . . .
C13 C 0.0793(11) 0.7588(8) 0.9426(5) 0.036(2) Uani 1 1 d . . . . .
C35 C 1.0120(13) 0.9184(10) 0.7518(7) 0.050(3) Uani 1 1 d . . . . .
H35 H 1.109549 0.905475 0.750933 0.060 Uiso 1 1 calc R U . . .
C3 C 0.0751(12) 0.7615(8) 0.5557(5) 0.035(2) Uani 1 1 d . . . . .
C34 C 0.9688(11) 1.0147(9) 0.7536(6) 0.042(3) Uani 1 1 d . . . . .
H34 H 1.035272 1.069607 0.756157 0.051 Uiso 1 1 calc R U . . .
N2 N 0.1771(10) 0.7669(7) 0.8843(4) 0.041(2) Uani 1 1 d . . . . .
C47 C 0.3071(10) 0.4658(9) 0.7444(6) 0.039(3) Uani 1 1 d . . . . .
C49 C 0.1722(12) 0.3129(9) 0.7535(6) 0.046(3) Uani 1 1 d . . . . .
H49 H 0.168967 0.240844 0.755100 0.055 Uiso 1 1 calc R U . . .
C39 C 0.5157(14) 0.5047(9) 0.6599(8) 0.056(3) Uani 1 1 d . . . . .
C12 C -0.0202(12) 0.6662(8) 0.5648(6) 0.039(3) Uani 1 1 d . . . . .
H12A H 0.037807 0.605301 0.569338 0.046 Uiso 1 1 calc R U . . .
H12B H -0.076917 0.674322 0.608338 0.046 Uiso 1 1 calc R U . . .
C16 C -0.0316(15) 0.6413(9) 1.0586(6) 0.051(3) Uani 1 1 d . . . . .
H16A H -0.096648 0.631045 1.098525 0.062 Uiso 1 1 calc R U . . .
H16B H 0.028302 0.581097 1.053924 0.062 Uiso 1 1 calc R U . . .
C19 C -0.0263(17) 0.8312(9) 1.0772(6) 0.060(4) Uani 1 1 d . . . . .
H19A H 0.037923 0.890710 1.085296 0.072 Uiso 1 1 calc R U . . .
H19B H -0.090879 0.827965 1.117959 0.072 Uiso 1 1 calc R U . . .
C20 C -0.1103(13) 0.8446(9) 1.0096(6) 0.046(3) Uani 1 1 d . . . . .
H20 H -0.168515 0.906592 1.014697 0.055 Uiso 1 1 calc R U . . .
C9 C -0.2069(12) 0.7478(9) 0.4954(6) 0.045(3) Uani 1 1 d . . . . .
H9A H -0.271292 0.740476 0.453974 0.054 Uiso 1 1 calc R U . . .
H9B H -0.264327 0.754627 0.538840 0.054 Uiso 1 1 calc R U . . .
C1 C 0.2423(12) 0.7752(8) 0.6648(6) 0.040(3) Uani 1 1 d . . . . .
C28 C 0.5268(12) 1.0320(8) 0.8252(7) 0.045(3) Uani 1 1 d . . . . .
C23 C 0.5648(10) 0.9755(8) 0.7517(6) 0.034(2) Uani 1 1 d . . . . .
C14 C -0.0147(14) 0.6652(9) 0.9275(6) 0.050(3) Uani 1 1 d . . . . .
H14A H -0.067500 0.672848 0.882551 0.060 Uiso 1 1 calc R U . . .
H14B H 0.043095 0.603911 0.922478 0.060 Uiso 1 1 calc R U . . .
C21 C -0.0127(13) 0.8546(8) 0.9472(6) 0.042(3) Uani 1 1 d . . . . .
H21A H 0.047638 0.916575 0.953721 0.050 Uiso 1 1 calc R U . . .
H21B H -0.067709 0.860298 0.902730 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0173(12) 0.8562(7) 0.5529(6) 0.038(2) Uani 1 1 d . . . . .
H8A H -0.073237 0.862993 0.596763 0.045 Uiso 1 1 calc R U . . .
H8B H 0.042250 0.918374 0.548734 0.045 Uiso 1 1 calc R U . . .
C48 C 0.2977(11) 0.3625(8) 0.7484(6) 0.036(2) Uani 1 1 d . . . . .
H48 H 0.381159 0.324423 0.747653 0.044 Uiso 1 1 calc R U . . .
C7 C -0.1137(13) 0.8423(8) 0.4885(5) 0.042(3) Uani 1 1 d . . . . .
H7 H -0.174098 0.903111 0.485273 0.050 Uiso 1 1 calc R U . . .
C4 C 0.1629(12) 0.7501(8) 0.4897(5) 0.038(2) Uani 1 1 d . . . . .
H4A H 0.223066 0.690215 0.493409 0.046 Uiso 1 1 calc R U . . .
H4B H 0.224426 0.811124 0.485063 0.046 Uiso 1 1 calc R U . . .
C10 C -0.1164(13) 0.6536(9) 0.4995(6) 0.046(3) Uani 1 1 d . . . . .
H10 H -0.178688 0.592046 0.504683 0.056 Uiso 1 1 calc R U . . .
C5 C 0.0661(12) 0.7367(8) 0.4233(6) 0.041(3) Uani 1 1 d . . . . .
H5 H 0.123453 0.729722 0.379265 0.049 Uiso 1 1 calc R U . . .
C38 C 0.4515(11) 0.5276(8) 0.7370(6) 0.041(3) Uani 1 1 d . . . . .
C2 C 0.2494(12) 0.7684(8) 0.8356(5) 0.039(2) Uani 1 1 d . . . . .
C42 C 0.4091(16) 0.5383(12) 0.6057(7) 0.074(4) Uani 1 1 d . . . . .
H42A H 0.323542 0.495971 0.608633 0.111 Uiso 1 1 calc R U . . .
H42B H 0.448346 0.531015 0.557923 0.111 Uiso 1 1 calc R U . . .
H42C H 0.386727 0.609643 0.615558 0.111 Uiso 1 1 calc R U . . .
C29 C 0.5983(19) 0.9795(12) 0.8857(7) 0.080(5) Uani 1 1 d . . . . .
H29A H 0.584333 0.905725 0.879437 0.119 Uiso 1 1 calc R U . . .
H29B H 0.557806 1.002347 0.930923 0.119 Uiso 1 1 calc R U . . .
H29C H 0.698934 0.996483 0.885702 0.119 Uiso 1 1 calc R U . . .
C26 C 0.5538(17) 0.9475(11) 0.6206(8) 0.072(4) Uani 1 1 d . . . . .
H26A H 0.497967 0.885142 0.627313 0.108 Uiso 1 1 calc R U . . .
H26B H 0.653844 0.932314 0.623230 0.108 Uiso 1 1 calc R U . . .
H26C H 0.532126 0.974583 0.574035 0.108 Uiso 1 1 calc R U . . .
C22 C -0.2078(13) 0.7485(9) 0.9944(6) 0.050(3) Uani 1 1 d . . . . .
H22A H -0.276283 0.741148 1.033229 0.060 Uiso 1 1 calc R U . . .
H22B H -0.260484 0.756117 0.949391 0.060 Uiso 1 1 calc R U . . .
C17 C 0.0584(14) 0.7353(10) 1.0730(6) 0.051(3) Uani 1 1 d . . . . .
H17 H 0.110790 0.728299 1.118764 0.062 Uiso 1 1 calc R U . . .
C11 C -0.0301(14) 0.6411(8) 0.4315(6) 0.045(3) Uani 1 1 d . . . . .
H11A H -0.093705 0.632467 0.389809 0.054 Uiso 1 1 calc R U . . .
H11B H 0.027714 0.579783 0.434036 0.054 Uiso 1 1 calc R U . . .
C18 C 0.1634(12) 0.7462(9) 1.0124(5) 0.048(3) Uani 1 1 d . . . . .
H18A H 0.221650 0.685007 1.008387 0.058 Uiso 1 1 calc R U . . .
H18B H 0.226099 0.806194 1.021745 0.058 Uiso 1 1 calc R U . . .
C24 C 0.5206(12) 1.0225(8) 0.6760(6) 0.042(3) Uani 1 1 d . . . . .
C25 C 0.3665(13) 1.0420(9) 0.6715(8) 0.058(3) Uani 1 1 d . . . . .
H25A H 0.346349 1.105890 0.697090 0.087 Uiso 1 1 calc R U . . .
H25B H 0.313864 0.985975 0.692774 0.087 Uiso 1 1 calc R U . . .
H25C H 0.338471 1.046767 0.621512 0.087 Uiso 1 1 calc R U . . .
C30 C 0.3727(15) 1.0278(10) 0.8383(9) 0.066(4) Uani 1 1 d . . . . .
H30A H 0.325043 1.071107 0.804807 0.099 Uiso 1 1 calc R U . . .
H30B H 0.354389 1.052062 0.887050 0.099 Uiso 1 1 calc R U . . .
H30C H 0.337491 0.957561 0.831768 0.099 Uiso 1 1 calc R U . . .
C15 C -0.1162(13) 0.6538(9) 0.9888(6) 0.047(3) Uani 1 1 d . . . . .
H15 H -0.177739 0.592068 0.979665 0.056 Uiso 1 1 calc R U . . .
C6 C -0.0271(12) 0.8316(8) 0.4201(6) 0.042(3) Uani 1 1 d . . . . .
H6A H 0.032925 0.893268 0.414769 0.050 Uiso 1 1 calc R U . . .
H6B H -0.090869 0.824778 0.378394 0.050 Uiso 1 1 calc R U . . .
C41 C 0.6492(18) 0.5652(12) 0.6475(10) 0.085(5) Uani 1 1 d . . . . .
H41A H 0.631109 0.637921 0.653521 0.127 Uiso 1 1 calc R U . . .
H41B H 0.681970 0.550772 0.599070 0.127 Uiso 1 1 calc R U . . .
H41C H 0.721126 0.546108 0.681679 0.127 Uiso 1 1 calc R U . . .
C31 C 0.5683(17) 1.1439(11) 0.8363(9) 0.075(5) Uani 1 1 d . . . . .
H31A H 0.663422 1.155709 0.818482 0.112 Uiso 1 1 calc R U . . .
H31B H 0.565667 1.162462 0.887073 0.112 Uiso 1 1 calc R U . . .
H31C H 0.502505 1.185648 0.810445 0.112 Uiso 1 1 calc R U . . .
C43 C 0.5440(17) 0.5117(9) 0.8087(9) 0.072(5) Uani 1 1 d . . . . .
C40 C 0.5424(19) 0.3934(11) 0.6405(10) 0.092(6) Uani 1 1 d . . . . .
H40A H 0.609915 0.366698 0.674278 0.138 Uiso 1 1 calc R U . . .
H40B H 0.580359 0.388127 0.592400 0.138 Uiso 1 1 calc R U . . .
H40C H 0.454080 0.354016 0.642499 0.138 Uiso 1 1 calc R U . . .
C44 C 0.449(2) 0.5134(14) 0.8728(8) 0.100(6) Uani 1 1 d . . . . .
H44A H 0.389231 0.451876 0.871726 0.150 Uiso 1 1 calc R U . . .
H44B H 0.390478 0.573500 0.871804 0.150 Uiso 1 1 calc R U . . .
H44C H 0.506487 0.516067 0.916257 0.150 Uiso 1 1 calc R U . . .
C27 C 0.6038(17) 1.1220(10) 0.6588(9) 0.077(5) Uani 1 1 d . . . . .
H27A H 0.568225 1.148615 0.614299 0.115 Uiso 1 1 calc R U . . .
H27B H 0.703541 1.107236 0.653891 0.115 Uiso 1 1 calc R U . . .
H27C H 0.591829 1.172671 0.697436 0.115 Uiso 1 1 calc R U . . .
C45 C 0.629(2) 0.4121(13) 0.8061(11) 0.108(7) Uani 1 1 d . . . . .
H45A H 0.640935 0.387708 0.854418 0.163 Uiso 1 1 calc R U . . .
H45B H 0.721639 0.425750 0.785611 0.163 Uiso 1 1 calc R U . . .
H45C H 0.578742 0.360107 0.776811 0.163 Uiso 1 1 calc R U . . .
C46 C 0.6578(19) 0.5927(11) 0.8169(10) 0.089(6) Uani 1 1 d . . . . .
H46A H 0.615759 0.657966 0.829670 0.134 Uiso 1 1 calc R U . . .
H46B H 0.708058 0.598538 0.771956 0.134 Uiso 1 1 calc R U . . .
H46C H 0.723536 0.574386 0.854360 0.134 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
Fe1 O1 1.803(8) . ?
Fe1 O2 1.758(9) . ?
Fe1 C1 2.091(11) . ?
Fe1 C2 2.083(11) . ?
O1 C23 1.418(11) . ?
O2 C38 1.462(13) . ?
C51 H51 0.9500 . ?
C51 C50 1.410(14) . ?
C51 C52 1.400(14) . ?
N1 C3 1.438(13) . ?
N1 C1 1.154(13) . ?
C50 H50 0.9500 . ?
C50 C49 1.367(16) . ?
C33 H33 0.9500 . ?
C33 C32 1.378(14) . ?
C33 C34 1.365(14) . ?
C37 H37 0.9500 . ?
C37 C36 1.364(15) . ?
C37 C32 1.397(14) . ?
C36 H36 0.9500 . ?
C36 C35 1.377(16) . ?
C52 H52 0.9500 . ?
C52 C47 1.390(14) . ?
C32 C23 1.570(15) . ?
C13 N2 1.450(13) . ?
C13 C14 1.525(15) . ?
C13 C21 1.554(15) . ?
C13 C18 1.550(14) . ?
C35 H35 0.9500 . ?
C35 C34 1.341(15) . ?
C3 C12 1.546(15) . ?
C3 C8 1.546(15) . ?
C3 C4 1.509(15) . ?
C34 H34 0.9500 . ?
N2 C2 1.153(13) . ?
C47 C48 1.366(13) . ?
C47 C38 1.592(15) . ?
C49 H49 0.9500 . ?
C49 C48 1.355(15) . ?
C39 C38 1.602(17) . ?
C39 C42 1.52(2) . ?
C39 C41 1.509(19) . ?
C39 C40 1.525(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C10 1.530(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.504(16) . ?
C16 C15 1.551(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.515(18) . ?
C19 C17 1.514(19) . ?
C20 H20 1.0000 . ?
C20 C21 1.513(15) . ?
C20 C22 1.569(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C7 1.521(15) . ?
C9 C10 1.532(17) . ?
C28 C23 1.598(17) . ?
C28 C29 1.516(18) . ?
C28 C30 1.492(18) . ?
C28 C31 1.523(16) . ?
C23 C24 1.628(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.520(15) . ?
C48 H48 0.9500 . ?
C7 H7 1.0000 . ?
C7 C6 1.539(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.551(14) . ?
C10 H10 1.0000 . ?
C10 C11 1.535(16) . ?
C5 H5 1.0000 . ?
C5 C11 1.551(15) . ?
C5 C6 1.553(16) . ?
C38 C43 1.628(16) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C24 1.455(19) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C15 1.540(17) . ?
C17 H17 1.0000 . ?
C17 C18 1.533(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C24 C25 1.500(17) . ?
C24 C27 1.559(16) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C15 H15 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C43 C44 1.51(3) . ?
C43 C45 1.56(2) . ?
C43 C46 1.506(19) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
O1 Fe1 C1 108.9(4) . . ?
O1 Fe1 C2 108.0(4) . . ?
O2 Fe1 O1 133.3(4) . . ?
O2 Fe1 C1 98.0(4) . . ?
O2 Fe1 C2 103.3(4) . . ?
C2 Fe1 C1 100.9(4) . . ?
C23 O1 Fe1 172.6(7) . . ?
C38 O2 Fe1 173.8(7) . . ?
C50 C51 H51 121.6 . . ?
C52 C51 H51 121.6 . . ?
C52 C51 C50 116.7(10) . . ?
C1 N1 C3 176.2(10) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 C51 120.4(10) . . ?
C49 C50 H50 119.8 . . ?
C32 C33 H33 118.5 . . ?
C34 C33 H33 118.5 . . ?
C34 C33 C32 123.1(11) . . ?
C36 C37 H37 118.7 . . ?
C36 C37 C32 122.6(10) . . ?
C32 C37 H37 118.7 . . ?
C37 C36 H36 120.7 . . ?
C37 C36 C35 118.7(11) . . ?
C35 C36 H36 120.7 . . ?
C51 C52 H52 119.0 . . ?
C47 C52 C51 122.1(10) . . ?
C47 C52 H52 119.0 . . ?
C33 C32 C37 115.2(10) . . ?
C33 C32 C23 124.3(10) . . ?
C37 C32 C23 120.4(9) . . ?
N2 C13 C14 107.8(8) . . ?
N2 C13 C21 110.0(8) . . ?
N2 C13 C18 108.8(9) . . ?
C14 C13 C21 109.2(10) . . ?
C14 C13 C18 109.9(9) . . ?
C18 C13 C21 111.2(8) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 C36 120.9(12) . . ?
C34 C35 H35 119.6 . . ?
N1 C3 C12 108.6(7) . . ?
N1 C3 C8 109.2(8) . . ?
N1 C3 C4 108.0(9) . . ?
C8 C3 C12 109.0(10) . . ?
C4 C3 C12 110.7(8) . . ?
C4 C3 C8 111.3(8) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.5(11) . . ?
C35 C34 H34 120.3 . . ?
C2 N2 C13 175.4(10) . . ?
C52 C47 C38 118.2(9) . . ?
C48 C47 C52 118.2(9) . . ?
C48 C47 C38 123.6(9) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 C50 121.0(11) . . ?
C48 C49 H49 119.5 . . ?
C42 C39 C38 107.2(10) . . ?
C42 C39 C40 105.4(13) . . ?
C41 C39 C38 112.6(12) . . ?
C41 C39 C42 106.7(12) . . ?
C41 C39 C40 108.0(13) . . ?
C40 C39 C38 116.3(10) . . ?
C3 C12 H12A 110.0 . . ?
C3 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C10 C12 C3 108.3(8) . . ?
C10 C12 H12A 110.0 . . ?
C10 C12 H12B 110.0 . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C17 C16 C15 109.2(9) . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C17 C19 H19A 109.3 . . ?
C17 C19 H19B 109.3 . . ?
C17 C19 C20 111.5(9) . . ?
C19 C20 H20 109.8 . . ?
C19 C20 C22 109.8(9) . . ?
C21 C20 C19 110.0(11) . . ?
C21 C20 H20 109.8 . . ?
C21 C20 C22 107.6(9) . . ?
C22 C20 H20 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C7 C9 H9A 109.7 . . ?
C7 C9 H9B 109.7 . . ?
C7 C9 C10 109.9(10) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
N1 C1 Fe1 173.7(9) . . ?
C29 C28 C23 109.2(9) . . ?
C29 C28 C31 104.6(11) . . ?
C30 C28 C23 111.5(10) . . ?
C30 C28 C29 107.6(12) . . ?
C30 C28 C31 104.5(10) . . ?
C31 C28 C23 118.8(10) . . ?
O1 C23 C32 108.9(8) . . ?
O1 C23 C28 103.9(8) . . ?
O1 C23 C24 105.6(8) . . ?
C32 C23 C28 109.2(9) . . ?
C32 C23 C24 107.6(9) . . ?
C28 C23 C24 121.0(8) . . ?
C13 C14 H14A 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 C13 108.7(8) . . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C13 C21 H21A 110.0 . . ?
C13 C21 H21B 110.0 . . ?
C20 C21 C13 108.3(9) . . ?
C20 C21 H21A 110.0 . . ?
C20 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C3 C8 H8A 110.2 . . ?
C3 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C7 C8 C3 107.5(8) . . ?
C7 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
C47 C48 H48 119.2 . . ?
C49 C48 C47 121.5(10) . . ?
C49 C48 H48 119.2 . . ?
C9 C7 H7 109.0 . . ?
C9 C7 C6 109.1(9) . . ?
C8 C7 C9 110.2(8) . . ?
C8 C7 H7 109.0 . . ?
C8 C7 C6 110.4(10) . . ?
C6 C7 H7 109.0 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C3 C4 C5 109.9(9) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C12 C10 C9 108.5(9) . . ?
C12 C10 H10 109.2 . . ?
C12 C10 C11 110.7(10) . . ?
C9 C10 H10 109.2 . . ?
C9 C10 C11 109.9(9) . . ?
C11 C10 H10 109.2 . . ?
C4 C5 H5 110.4 . . ?
C4 C5 C11 109.1(8) . . ?
C4 C5 C6 107.8(8) . . ?
C11 C5 H5 110.4 . . ?
C11 C5 C6 108.7(10) . . ?
C6 C5 H5 110.4 . . ?
O2 C38 C47 108.8(8) . . ?
O2 C38 C39 104.5(8) . . ?
O2 C38 C43 104.7(8) . . ?
C47 C38 C39 109.4(9) . . ?
C47 C38 C43 107.9(10) . . ?
C39 C38 C43 120.9(11) . . ?
N2 C2 Fe1 177.5(10) . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
C20 C22 H22A 109.9 . . ?
C20 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C15 C22 C20 108.8(11) . . ?
C15 C22 H22A 109.9 . . ?
C15 C22 H22B 109.9 . . ?
C16 C17 C19 112.6(12) . . ?
C16 C17 H17 109.3 . . ?
C16 C17 C18 108.7(9) . . ?
C19 C17 H17 109.3 . . ?
C19 C17 C18 107.7(10) . . ?
C18 C17 H17 109.3 . . ?
C10 C11 C5 109.3(8) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C5 C11 H11A 109.8 . . ?
C5 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C13 C18 H18A 110.1 . . ?
C13 C18 H18B 110.1 . . ?
C17 C18 C13 108.1(9) . . ?
C17 C18 H18A 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C26 C24 C23 107.3(9) . . ?
C26 C24 C25 107.9(11) . . ?
C26 C24 C27 106.7(13) . . ?
C25 C24 C23 112.2(10) . . ?
C25 C24 C27 108.9(9) . . ?
C27 C24 C23 113.5(9) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C16 C15 H15 109.3 . . ?
C14 C15 C16 109.1(10) . . ?
C14 C15 C22 109.1(10) . . ?
C14 C15 H15 109.3 . . ?
C22 C15 C16 110.7(9) . . ?
C22 C15 H15 109.3 . . ?
C7 C6 C5 110.0(8) . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C44 C43 C38 109.7(12) . . ?
C44 C43 C45 110.0(13) . . ?
C45 C43 C38 113.4(12) . . ?
C46 C43 C38 110.7(11) . . ?
C46 C43 C44 110.5(13) . . ?
C46 C43 C45 102.4(15) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
O1 C23 C24 C26 -55.5(12) . . . . ?
O1 C23 C24 C25 62.9(11) . . . . ?
O1 C23 C24 C27 -173.1(11) . . . . ?
O2 C38 C43 C44 76.5(12) . . . . ?
O2 C38 C43 C45 -160.1(13) . . . . ?
O2 C38 C43 C46 -45.7(16) . . . . ?
C51 C50 C49 C48 0.7(17) . . . . ?
C51 C52 C47 C48 1.6(15) . . . . ?
C51 C52 C47 C38 -179.1(11) . . . . ?
N1 C3 C12 C10 -178.3(9) . . . . ?
N1 C3 C8 C7 179.6(8) . . . . ?
N1 C3 C4 C5 179.1(8) . . . . ?
C50 C51 C52 C47 -2.3(15) . . . . ?
C50 C49 C48 C47 -1.5(17) . . . . ?
C33 C32 C23 O1 -175.7(10) . . . . ?
C33 C32 C23 C28 -62.8(13) . . . . ?
C33 C32 C23 C24 70.2(13) . . . . ?
C37 C36 C35 C34 3.0(16) . . . . ?
C37 C32 C23 O1 1.6(13) . . . . ?
C37 C32 C23 C28 114.6(10) . . . . ?
C37 C32 C23 C24 -112.4(10) . . . . ?
C36 C37 C32 C33 1.1(14) . . . . ?
C36 C37 C32 C23 -176.5(11) . . . . ?
C36 C35 C34 C33 -2.9(16) . . . . ?
C52 C51 C50 C49 1.1(14) . . . . ?
C52 C47 C48 C49 0.3(15) . . . . ?
C52 C47 C38 O2 3.8(13) . . . . ?
C52 C47 C38 C39 -109.8(11) . . . . ?
C52 C47 C38 C43 116.9(12) . . . . ?
C32 C33 C34 C35 1.9(17) . . . . ?
C32 C37 C36 C35 -2.1(16) . . . . ?
C32 C23 C24 C26 60.8(12) . . . . ?
C32 C23 C24 C25 179.1(9) . . . . ?
C32 C23 C24 C27 -56.9(13) . . . . ?
C13 C14 C15 C16 -59.9(13) . . . . ?
C13 C14 C15 C22 61.2(13) . . . . ?
C3 C12 C10 C9 -61.1(12) . . . . ?
C3 C12 C10 C11 59.6(12) . . . . ?
C3 C8 C7 C9 60.8(12) . . . . ?
C3 C8 C7 C6 -59.8(11) . . . . ?
C3 C4 C5 C11 -59.1(11) . . . . ?
C3 C4 C5 C6 58.8(11) . . . . ?
C34 C33 C32 C37 -0.9(16) . . . . ?
C34 C33 C32 C23 176.5(12) . . . . ?
N2 C13 C14 C15 178.7(9) . . . . ?
N2 C13 C21 C20 -178.5(9) . . . . ?
N2 C13 C18 C17 -178.7(9) . . . . ?
C47 C38 C43 C44 -39.2(13) . . . . ?
C47 C38 C43 C45 84.2(16) . . . . ?
C47 C38 C43 C46 -161.4(13) . . . . ?
C39 C38 C43 C44 -166.2(11) . . . . ?
C39 C38 C43 C45 -42.7(18) . . . . ?
C39 C38 C43 C46 71.6(16) . . . . ?
C12 C3 C8 C7 -61.8(10) . . . . ?
C12 C3 C4 C5 60.3(11) . . . . ?
C12 C10 C11 C5 -59.9(12) . . . . ?
C16 C17 C18 C13 61.9(13) . . . . ?
C19 C20 C21 C13 57.1(12) . . . . ?
C19 C20 C22 C15 -57.7(12) . . . . ?
C19 C17 C18 C13 -60.4(12) . . . . ?
C20 C19 C17 C16 -57.3(13) . . . . ?
C20 C19 C17 C18 62.6(14) . . . . ?
C20 C22 C15 C16 58.9(12) . . . . ?
C20 C22 C15 C14 -61.2(12) . . . . ?
C9 C7 C6 C5 -60.2(12) . . . . ?
C9 C10 C11 C5 60.0(12) . . . . ?
C28 C23 C24 C26 -172.9(11) . . . . ?
C28 C23 C24 C25 -54.5(13) . . . . ?
C28 C23 C24 C27 69.5(14) . . . . ?
C14 C13 C21 C20 63.5(11) . . . . ?
C14 C13 C18 C17 -61.0(12) . . . . ?
C21 C13 C14 C15 -61.9(12) . . . . ?
C21 C13 C18 C17 60.0(12) . . . . ?
C21 C20 C22 C15 62.1(12) . . . . ?
C8 C3 C12 C10 62.8(11) . . . . ?
C8 C3 C4 C5 -61.0(11) . . . . ?
C8 C7 C6 C5 61.1(11) . . . . ?
C48 C47 C38 O2 -176.9(8) . . . . ?
C48 C47 C38 C39 69.4(12) . . . . ?
C48 C47 C38 C43 -63.9(13) . . . . ?
C7 C9 C10 C12 60.4(11) . . . . ?
C7 C9 C10 C11 -60.8(11) . . . . ?
C4 C3 C12 C10 -59.9(12) . . . . ?
C4 C3 C8 C7 60.5(12) . . . . ?
C4 C5 C11 C10 58.4(13) . . . . ?
C4 C5 C6 C7 -58.7(12) . . . . ?
C10 C9 C7 C8 -61.0(12) . . . . ?
C10 C9 C7 C6 60.4(11) . . . . ?
C38 C47 C48 C49 -178.9(12) . . . . ?
C42 C39 C38 O2 -56.4(11) . . . . ?
C42 C39 C38 C47 59.9(12) . . . . ?
C42 C39 C38 C43 -173.8(10) . . . . ?
C29 C28 C23 O1 69.7(12) . . . . ?
C29 C28 C23 C32 -46.4(13) . . . . ?
C29 C28 C23 C24 -172.0(11) . . . . ?
C22 C20 C21 C13 -62.5(12) . . . . ?
C17 C16 C15 C14 61.8(13) . . . . ?
C17 C16 C15 C22 -58.3(13) . . . . ?
C17 C19 C20 C21 -61.7(14) . . . . ?
C17 C19 C20 C22 56.6(14) . . . . ?
C11 C5 C6 C7 59.4(11) . . . . ?
C18 C13 C14 C15 60.3(13) . . . . ?
C18 C13 C21 C20 -57.9(12) . . . . ?
C30 C28 C23 O1 -49.1(12) . . . . ?
C30 C28 C23 C32 -165.2(10) . . . . ?
C30 C28 C23 C24 69.2(13) . . . . ?
C15 C16 C17 C19 56.7(12) . . . . ?
C15 C16 C17 C18 -62.6(13) . . . . ?
C6 C5 C11 C10 -59.0(11) . . . . ?
C41 C39 C38 O2 60.5(14) . . . . ?
C41 C39 C38 C47 176.9(11) . . . . ?
C41 C39 C38 C43 -56.9(15) . . . . ?
C31 C28 C23 O1 -170.6(9) . . . . ?
C31 C28 C23 C32 73.3(12) . . . . ?
C31 C28 C23 C24 -52.3(13) . . . . ?
C40 C39 C38 O2 -174.0(12) . . . . ?
C40 C39 C38 C47 -57.7(15) . . . . ?
C40 C39 C38 C43 68.6(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.531(3)
2 0.469(3)

_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# 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_sg984
_database_code_depnum_ccdc_archive 'CCDC 2351178'
loop_
_audit_author_name
_audit_author_address
'Stanislav Groysman'
;Wayne State University
United States of America
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2024-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H20 O8, C7 H8'
_chemical_formula_sum            'C37 H28 O8'
_chemical_formula_weight         600.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3230(7)
_cell_length_b                   19.0774(14)
_cell_length_c                   8.7024(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.576(2)
_cell_angle_gamma                90
_cell_volume                     1558.56(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.361
_cell_measurement_theta_min      2.418
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1190 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.9416.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            42299
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.644
_diffrn_reflns_theta_min         2.418
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Photon III'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.8 mm pinhole collimator'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2497
_reflns_number_total             3217
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     734
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.6553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1S-C2S
 1.51 with sigma of 0.02
 C2S-C3S = C2S-C7S = C4S-C5S
 1.39 with sigma of 0.02
 C3S-C4S = C5S-C6S = C6S-C7S
 1.38 with sigma of 0.02
 C1S-C3S = C1S-C7S
 2.52 with sigma of 0.04
 C2S-C4S
 2.42 with sigma of 0.04
 C2S-C6S
 2.41 with sigma of 0.04
 C3S-C5S
 2.39 with sigma of 0.04
 C4S-C6S = C5S-C7S
 2.4 with sigma of 0.04
 C2S-C3S \\sim C3S-C4S \\sim C4S-C5S \\sim C5S-C6S \\sim C6S-C7S \\sim C7S-C2S
 with sigma of 0.02
 C2S-C6S \\sim C2S-C4S \\sim C7S-C5S \\sim C3S-C7S \\sim C4S-C6S \\sim C3S-C5S
 with sigma of 0.04
 C1S-C7S \\sim C1S-C3S
 with sigma of 0.04
 C7-C4 \\sim C8-C7 \\sim C8-C1 \\sim C2-C1 \\sim C3-C2 \\sim C4-C3 \\sim
C7B-C4B \\sim C7B-C8B \\sim C1B-C8B ~
 C2B-C1B \\sim C3B-C2B \\sim C3B-C4B
 with sigma of 0.02
 C4-C8 \\sim C7-C1 \\sim C4B-C8B \\sim C7B-C1B \\sim C8-C2 \\sim C1-C3 \\sim
C2-C4 \\sim C8B-C2B \\sim C1B-C3B
 \\sim C2B-C4B
 with sigma of 0.02
 C12B-C11B \\sim C15B-C12B \\sim C14B-C15B \\sim C10B-C9B \\sim C10B-C11B \\sim
C11-C10 \\sim C12-C11
 \\sim C15-C12 \\sim C15-C14 \\sim C9-C14 \\sim C9-C10 \\sim C14B-C9B
 with sigma of 0.02
 C12-C14 \\sim C15-C9 \\sim C12B-C14B \\sim C15B-C9B \\sim C14B-C10B \\sim
C9B-C11B \\sim C10B-C12B ~
 C14-C10 \\sim C9-C11 \\sim C10-C12 \\sim C11-C15
 with sigma of 0.02
3. Restrained planarity
 C1S, C2S, C3S, C4S, C5S, C6S, C7S
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C1S \\sim C2S \\sim C3S \\sim C4S \\sim C5S \\sim C6S \\sim C7S: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C7 \\sim C8 \\sim C1B \\sim C2B \\sim C3B
\\sim C4B \\sim C7B \\sim C8B: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.02 within 2A
C9 \\sim C10 \\sim C11 \\sim C12 \\sim C14 \\sim C15 \\sim C9B \\sim C10B \\sim
C11B \\sim C12B \\sim C14B \\sim C15B: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 C1S, C2S, C3S, C4S, C5S, C6S, C7S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(C7B)=
 Sof(H7B)=Sof(C8B)=Sof(H8B)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C7)=Sof(H7)=
 Sof(C8)=Sof(H8)=FVAR(1)
 Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(C14B)=
 Sof(H14B)=Sof(C15B)=Sof(H15B)=1-FVAR(2)
 Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(C14)=
 Sof(H14)=Sof(C15)=Sof(H15)=FVAR(2)
 Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C2S(0.5) C3S(0.5) H3S(0.5)
 C4S(0.5) H4S(0.5) C5S(0.5) H5S(0.5) C6S(0.5) H6S(0.5) C7S(0.5) H7S(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C1B(H1B), C2B(H2B), C3B(H3B), C7B(H7B), C8B(H8B), C9B(H9B),
 C10B(H10B), C11B(H11B), C14B(H14B), C15B(H15B), C3S(H3S), C4S(H4S), C5S(H5S),
 C6S(H6S), C7S(H7S)
7.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.77450(12) 0.43420(6) 0.57227(17) 0.0474(3) Uani 1 1 d . . . . .
O2 O 0.97078(13) 0.55543(6) 0.77304(15) 0.0469(3) Uani 1 1 d . . . . .
O3 O 0.80662(14) 0.59607(6) 0.52330(16) 0.0516(3) Uani 1 1 d . . . . .
O4 O 0.89275(14) 0.37776(6) 0.44179(18) 0.0556(4) Uani 1 1 d . . . . .
C5 C 0.87080(18) 0.42897(8) 0.5072(2) 0.0438(4) Uani 1 1 d . . . . .
C6 C 0.94884(18) 0.49676(8) 0.5270(2) 0.0442(4) Uani 1 1 d . . . . .
C13 C 0.89971(18) 0.55652(8) 0.6035(2) 0.0435(4) Uani 1 1 d . . . . .
C1 C 0.5451(12) 0.2630(5) 0.6009(19) 0.055(2) Uani 0.53(3) 1 d D U P A 1
H1 H 0.491166 0.223191 0.604683 0.066 Uiso 0.53(3) 1 calc R U P A 1
C2 C 0.6866(12) 0.2670(5) 0.7096(18) 0.0515(19) Uani 0.53(3) 1 d D U P A 1
H2 H 0.728205 0.231430 0.791847 0.062 Uiso 0.53(3) 1 calc R U P A 1
C3 C 0.7690(12) 0.3228(5) 0.7001(17) 0.0397(17) Uani 0.53(3) 1 d D U P A 1
H3 H 0.868331 0.324893 0.769172 0.048 Uiso 0.53(3) 1 calc R U P A 1
C4 C 0.7000(11) 0.3751(6) 0.5856(16) 0.0319(18) Uani 0.53(3) 1 d D U P A 1
C7 C 0.5585(12) 0.3735(5) 0.4781(17) 0.0401(19) Uani 0.53(3) 1 d D U P A 1
H7 H 0.515557 0.410581 0.400652 0.048 Uiso 0.53(3) 1 calc R U P A 1
C8 C 0.4801(11) 0.3157(6) 0.4864(19) 0.055(2) Uani 0.53(3) 1 d D U P A 1
H8 H 0.381667 0.312551 0.413343 0.066 Uiso 0.53(3) 1 calc R U P A 1
C9 C 0.8578(15) 0.7123(8) 1.0265(14) 0.047(2) Uani 0.47(3) 1 d D U P B 1
H9 H 0.824299 0.748399 1.075934 0.057 Uiso 0.47(3) 1 calc R U P B 1
C10 C 0.9415(15) 0.7293(5) 0.9442(16) 0.0440(19) Uani 0.47(3) 1 d D U P B 1
H10 H 0.971963 0.776342 0.945168 0.053 Uiso 0.47(3) 1 calc R U P B 1
C11 C 0.9820(17) 0.6779(6) 0.8593(19) 0.0398(19) Uani 0.47(3) 1 d D U P B 1
H11 H 1.038327 0.689121 0.799755 0.048 Uiso 0.47(3) 1 calc R U P B 1
C12 C 0.938(3) 0.6106(7) 0.865(4) 0.042(3) Uani 0.47(3) 1 d D U P B 1
C14 C 0.8213(14) 0.6436(8) 1.0386(13) 0.049(2) Uani 0.47(3) 1 d D U P B 1
H14 H 0.771206 0.631441 1.104894 0.059 Uiso 0.47(3) 1 calc R U P B 1
C15 C 0.8598(17) 0.5929(7) 0.952(2) 0.056(3) Uani 0.47(3) 1 d D U P B 1
H15 H 0.831387 0.545615 0.952545 0.067 Uiso 0.47(3) 1 calc R U P B 1
C1B C 0.5240(13) 0.2576(6) 0.541(3) 0.059(3) Uani 0.47(3) 1 d D U P A 2
H1B H 0.466157 0.218740 0.540640 0.071 Uiso 0.47(3) 1 calc R U P A 2
C2B C 0.6656(13) 0.2591(6) 0.654(2) 0.052(2) Uani 0.47(3) 1 d D U P A 2
H2B H 0.706760 0.220885 0.728616 0.062 Uiso 0.47(3) 1 calc R U P A 2
C3B C 0.7459(15) 0.3170(8) 0.657(2) 0.053(3) Uani 0.47(3) 1 d D U P A 2
H3B H 0.842147 0.319967 0.737329 0.064 Uiso 0.47(3) 1 calc R U P A 2
C4B C 0.6881(14) 0.3699(7) 0.545(2) 0.042(3) Uani 0.47(3) 1 d D U P A 2
C7B C 0.5491(14) 0.3685(6) 0.430(2) 0.050(3) Uani 0.47(3) 1 d D U P A 2
H7B H 0.510341 0.405604 0.350973 0.060 Uiso 0.47(3) 1 calc R U P A 2
C8B C 0.4667(12) 0.3115(6) 0.430(2) 0.055(3) Uani 0.47(3) 1 d D U P A 2
H8B H 0.369214 0.309834 0.352979 0.066 Uiso 0.47(3) 1 calc R U P A 2
C9B C 0.8252(12) 0.6915(8) 1.0349(13) 0.049(2) Uani 0.53(3) 1 d D U P B 2
H9B H 0.795477 0.722375 1.099679 0.058 Uiso 0.53(3) 1 calc R U P B 2
C10B C 0.9028(15) 0.7169(5) 0.9527(14) 0.046(2) Uani 0.53(3) 1 d D U P B 2
H10B H 0.922591 0.765629 0.954427 0.056 Uiso 0.53(3) 1 calc R U P B 2
C11B C 0.9519(16) 0.6707(7) 0.8670(18) 0.047(2) Uani 0.53(3) 1 d D U P B 2
H11B H 1.009626 0.687364 0.813607 0.057 Uiso 0.53(3) 1 calc R U P B 2
C12B C 0.918(3) 0.6016(7) 0.859(3) 0.039(2) Uani 0.53(3) 1 d D U P B 2
C14B C 0.7898(13) 0.6218(8) 1.0248(14) 0.058(2) Uani 0.53(3) 1 d D U P B 2
H14B H 0.730991 0.605388 1.077013 0.069 Uiso 0.53(3) 1 calc R U P B 2
C15B C 0.8390(14) 0.5753(6) 0.9393(16) 0.0431(17) Uani 0.53(3) 1 d D U P B 2
H15B H 0.818752 0.526596 0.936445 0.052 Uiso 0.53(3) 1 calc R U P B 2
C1S C 0.4053(15) 0.5896(5) 1.1081(17) 0.177(6) Uani 0.5 1 d D U P C -1
H1SA H 0.311849 0.602818 1.020985 0.266 Uiso 0.5 1 calc R U P C -1
H1SB H 0.467923 0.630684 1.139682 0.266 Uiso 0.5 1 calc R U P C -1
H1SC H 0.394189 0.571920 1.207689 0.266 Uiso 0.5 1 calc R U P C -1
C2S C 0.4688(6) 0.5340(2) 1.0412(6) 0.0725(14) Uani 0.5 1 d D U P C -1
C3S C 0.4188(7) 0.5191(3) 0.8704(9) 0.0753(18) Uani 0.5 1 d D U P C -1
H3S H 0.354284 0.550552 0.790407 0.090 Uiso 0.5 1 calc R U P C -1
C4S C 0.4594(7) 0.4616(4) 0.8168(8) 0.109(2) Uani 0.5 1 d D U P C -1
H4S H 0.405667 0.445861 0.704505 0.130 Uiso 0.5 1 calc R U P C -1
C5S C 0.5725(7) 0.4258(4) 0.9157(8) 0.0766(16) Uani 0.5 1 d D U P C -1
H5S H 0.603123 0.386183 0.873504 0.092 Uiso 0.5 1 calc R U P C -1
C6S C 0.6441(7) 0.4462(4) 1.0774(7) 0.110(2) Uani 0.5 1 d D U P C -1
H6S H 0.719147 0.418486 1.155449 0.133 Uiso 0.5 1 calc R U P C -1
C7S C 0.6041(8) 0.5099(3) 1.1271(9) 0.085(2) Uani 0.5 1 d D U P C -1
H7S H 0.670735 0.535746 1.219380 0.102 Uiso 0.5 1 calc R U P C -1


_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 C5 1.337(2) . ?
O1 C4 1.397(10) . ?
O1 C4B 1.477(12) . ?
O2 C13 1.347(2) . ?
O2 C12 1.444(11) . ?
O2 C12B 1.400(10) . ?
O3 C13 1.193(2) . ?
O4 C5 1.1986(19) . ?
C5 C6 1.495(2) . ?
C6 C6 1.328(3) 3_766 ?
C6 C13 1.510(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(9) . ?
C1 C8 1.379(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(8) . ?
C4 C7 1.369(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.371(8) . ?
C9 C14 1.379(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.369(10) . ?
C12 C15 1.358(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(9) . ?
C15 H15 0.9500 . ?
C1B H1B 0.9500 . ?
C1B C2B 1.382(9) . ?
C1B C8B 1.366(10) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.375(9) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.355(10) . ?
C4B C7B 1.367(10) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.382(9) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C9B C10B 1.366(7) . ?
C9B C14B 1.372(7) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.380(9) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.358(9) . ?
C12B C15B 1.375(9) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.384(8) . ?
C15B H15B 0.9500 . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S C2S 1.487(7) . ?
C2S C3S 1.385(7) . ?
C2S C7S 1.360(8) . ?
C3S H3S 0.9500 . ?
C3S C4S 1.327(8) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.317(8) . ?
C5S H5S 0.9500 . ?
C5S C6S 1.346(8) . ?
C6S H6S 0.9500 . ?
C6S C7S 1.408(8) . ?
C7S H7S 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
C5 O1 C4 120.5(6) . . ?
C5 O1 C4B 112.1(7) . . ?
C13 O2 C12 116.6(13) . . ?
C13 O2 C12B 114.7(12) . . ?
O1 C5 C6 110.28(13) . . ?
O4 C5 O1 125.63(15) . . ?
O4 C5 C6 124.09(15) . . ?
C5 C6 C13 116.10(14) . . ?
C6 C6 C5 120.62(18) 3_766 . ?
C6 C6 C13 123.22(19) 3_766 . ?
O2 C13 C6 109.97(15) . . ?
O3 C13 O2 126.15(15) . . ?
O3 C13 C6 123.78(17) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C8 121.0(7) . . ?
C8 C1 H1 119.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(7) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 121.5 . . ?
C4 C3 C2 116.9(7) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 O1 120.5(7) . . ?
C7 C4 O1 115.4(7) . . ?
C7 C4 C3 124.1(8) . . ?
C4 C7 H7 121.2 . . ?
C4 C7 C8 117.5(7) . . ?
C8 C7 H7 121.2 . . ?
C1 C8 C7 119.9(7) . . ?
C1 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 H9 119.5 . . ?
C10 C9 C14 121.1(7) . . ?
C14 C9 H9 119.5 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.3(6) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.6(7) . . ?
C12 C11 H11 121.2 . . ?
C11 C12 O2 120.5(9) . . ?
C15 C12 O2 117.1(9) . . ?
C15 C12 C11 122.4(8) . . ?
C9 C14 H14 120.9 . . ?
C9 C14 C15 118.2(7) . . ?
C15 C14 H14 120.9 . . ?
C12 C15 C14 120.2(7) . . ?
C12 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C2B C1B H1B 119.8 . . ?
C8B C1B H1B 119.8 . . ?
C8B C1B C2B 120.4(8) . . ?
C1B C2B H2B 120.6 . . ?
C3B C2B C1B 118.7(7) . . ?
C3B C2B H2B 120.6 . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B C2B 120.2(8) . . ?
C4B C3B H3B 119.9 . . ?
C3B C4B O1 116.5(9) . . ?
C3B C4B C7B 121.8(9) . . ?
C7B C4B O1 120.9(10) . . ?
C4B C7B H7B 120.9 . . ?
C4B C7B C8B 118.2(9) . . ?
C8B C7B H7B 120.9 . . ?
C1B C8B C7B 120.6(8) . . ?
C1B C8B H8B 119.7 . . ?
C7B C8B H8B 119.7 . . ?
C10B C9B H9B 119.7 . . ?
C10B C9B C14B 120.6(6) . . ?
C14B C9B H9B 119.7 . . ?
C9B C10B H10B 120.5 . . ?
C9B C10B C11B 118.9(6) . . ?
C11B C10B H10B 120.5 . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B C10B 120.4(7) . . ?
C12B C11B H11B 119.8 . . ?
C11B C12B O2 119.5(8) . . ?
C11B C12B C15B 121.4(7) . . ?
C15B C12B O2 119.1(9) . . ?
C9B C14B H14B 119.7 . . ?
C9B C14B C15B 120.6(6) . . ?
C15B C14B H14B 119.7 . . ?
C12B C15B C14B 118.0(7) . . ?
C12B C15B H15B 121.0 . . ?
C14B C15B H15B 121.0 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
C3S C2S C1S 122.5(7) . . ?
C7S C2S C1S 123.0(7) . . ?
C7S C2S C3S 111.1(5) . . ?
C2S C3S H3S 119.5 . . ?
C4S C3S C2S 121.0(5) . . ?
C4S C3S H3S 119.5 . . ?
C3S C4S H4S 119.2 . . ?
C5S C4S C3S 121.6(6) . . ?
C5S C4S H4S 119.2 . . ?
C4S C5S H5S 120.5 . . ?
C4S C5S C6S 119.0(6) . . ?
C6S C5S H5S 120.5 . . ?
C5S C6S H6S 121.1 . . ?
C5S C6S C7S 117.8(6) . . ?
C7S C6S H6S 121.1 . . ?
C2S C7S C6S 119.2(5) . . ?
C2S C7S H7S 120.4 . . ?
C6S C7S H7S 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C6 179.1(2) . . . 3_766 ?
O1 C5 C6 C13 -3.4(2) . . . . ?
O1 C4 C7 C8 179.9(9) . . . . ?
O1 C4B C7B C8B -168.8(12) . . . . ?
O2 C12 C15 C14 -178.3(17) . . . . ?
O2 C12B C15B C14B 179.1(16) . . . . ?
O4 C5 C6 C6 -1.0(4) . . . 3_766 ?
O4 C5 C6 C13 176.49(18) . . . . ?
C5 O1 C4 C3 69.8(13) . . . . ?
C5 O1 C4 C7 -109.6(9) . . . . ?
C5 O1 C4B C3B 82.9(14) . . . . ?
C5 O1 C4B C7B -106.9(12) . . . . ?
C5 C6 C13 O2 88.94(18) . . . . ?
C5 C6 C13 O3 -87.8(2) . . . . ?
C6 C6 C13 O2 -93.7(3) 3_766 . . . ?
C6 C6 C13 O3 89.6(3) 3_766 . . . ?
C13 O2 C12 C11 -72(3) . . . . ?
C13 O2 C12 C15 107(2) . . . . ?
C13 O2 C12B C11B -79(2) . . . . ?
C13 O2 C12B C15B 104(2) . . . . ?
C1 C2 C3 C4 4.2(16) . . . . ?
C2 C1 C8 C7 1.1(14) . . . . ?
C2 C3 C4 O1 177.8(10) . . . . ?
C2 C3 C4 C7 -2.8(18) . . . . ?
C3 C4 C7 C8 0.5(17) . . . . ?
C4 O1 C5 O4 7.4(6) . . . . ?
C4 O1 C5 C6 -172.7(5) . . . . ?
C4 C7 C8 C1 0.4(14) . . . . ?
C8 C1 C2 C3 -3.5(15) . . . . ?
C9 C10 C11 C12 -1(2) . . . . ?
C9 C14 C15 C12 4(2) . . . . ?
C10 C9 C14 C15 -6.2(18) . . . . ?
C10 C11 C12 O2 177.2(19) . . . . ?
C10 C11 C12 C15 -1(4) . . . . ?
C11 C12 C15 C14 0(4) . . . . ?
C12 O2 C13 O3 -4.9(8) . . . . ?
C12 O2 C13 C6 178.5(7) . . . . ?
C14 C9 C10 C11 5.2(19) . . . . ?
C1B C2B C3B C4B -3(2) . . . . ?
C2B C1B C8B C7B -0.1(16) . . . . ?
C2B C3B C4B O1 171.5(12) . . . . ?
C2B C3B C4B C7B 1(2) . . . . ?
C3B C4B C7B C8B 1(2) . . . . ?
C4B O1 C5 O4 -3.8(7) . . . . ?
C4B O1 C5 C6 176.1(6) . . . . ?
C4B C7B C8B C1B -1.4(18) . . . . ?
C8B C1B C2B C3B 2.4(16) . . . . ?
C9B C10B C11B C12B 3(2) . . . . ?
C9B C14B C15B C12B -3(2) . . . . ?
C10B C9B C14B C15B 3.8(17) . . . . ?
C10B C11B C12B O2 -179.1(16) . . . . ?
C10B C11B C12B C15B -2(3) . . . . ?
C11B C12B C15B C14B 2(3) . . . . ?
C12B O2 C13 O3 6.2(7) . . . . ?
C12B O2 C13 C6 -170.4(6) . . . . ?
C14B C9B C10B C11B -3.6(16) . . . . ?
C1S C2S C3S C4S -167.6(7) . . . . ?
C1S C2S C7S C6S 163.9(7) . . . . ?
C2S C3S C4S C5S -17.0(11) . . . . ?
C3S C2S C7S C6S -36.4(8) . . . . ?
C3S C4S C5S C6S 3.4(11) . . . . ?
C4S C5S C6S C7S -7.4(11) . . . . ?
C5S C6S C7S C2S 25.7(10) . . . . ?
C7S C2S C3S C4S 32.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sg974_0m
_database_code_depnum_ccdc_archive 'CCDC 2351177'
loop_
_audit_author_name
_audit_author_address
'Stanislav Groysman'
;Wayne State University
United States of America
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_audit_creation_date             2024-04-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H6 O4'
_chemical_formula_sum            'C5 H6 O4'
_chemical_formula_weight         130.101
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.0060(4)
_cell_length_b                   7.2628(8)
_cell_length_c                   8.6451(8)
_cell_angle_alpha                106.710(4)
_cell_angle_beta                 102.405(3)
_cell_angle_gamma                92.116(3)
_cell_volume                     292.37(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1050
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      4.19
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             136.127
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.9820
_diffrn_reflns_Laue_measured_fraction_max 0.9863
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9727
_diffrn_reflns_point_group_measured_fraction_full 0.9820
_diffrn_reflns_point_group_measured_fraction_max 0.9863
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         4.19
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.9820
_diffrn_measured_fraction_theta_max 0.9863
_diffrn_measurement_device_type  'Bruker A8 Advance'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1050
_reflns_number_total             1436
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.3283
_refine_diff_density_min         -0.2965
_refine_diff_density_rms         0.0751
_refine_ls_d_res_high            0.7503
_refine_ls_d_res_low             4.8618
_refine_ls_goodness_of_fit_ref   1.0019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.0019
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.0229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1077
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C5(H5a,H5b,H5c)
;
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_refinement_flags_posn
O2 O 0.0989(2) 0.76147(14) 0.41881(12) 0.0199(3) Uani 1.000000 .
O4 O 0.2323(2) 0.65215(14) 0.74378(12) 0.0180(3) Uani 1.000000 .
O3 O 0.5908(2) 0.85149(15) 0.74822(13) 0.0224(3) Uani 1.000000 .
O1 O 0.2836(2) 0.56352(15) 0.22661(12) 0.0209(3) Uani 1.000000 .
C4 C -0.0778(3) 0.8208(2) 0.28873(19) 0.0233(4) Uani 1.000000 .
H4a H 0.0346(4) 0.8939(14) 0.2420(10) 0.0349(5) Uiso 1.000000 GR
H4b H -0.1770(17) 0.7061(2) 0.2009(7) 0.0349(5) Uiso 1.000000 GR
H4c H -0.2102(15) 0.9025(13) 0.3355(3) 0.0349(5) Uiso 1.000000 GR
C2 C 0.2641(3) 0.6300(2) 0.36757(17) 0.0158(3) Uani 1.000000 .
C1 C 0.4280(3) 0.5761(2) 0.51242(17) 0.0159(3) Uani 1.000000 .
C5 C 0.2322(3) 0.7661(2) 0.91243(17) 0.0218(3) Uani 1.000000 .
H5a H 0.214(2) 0.9012(4) 0.9165(3) 0.0326(5) Uiso 1.000000 GR
H5b H 0.0775(13) 0.7155(10) 0.9464(5) 0.0326(5) Uiso 1.000000 GR
H5c H 0.4051(10) 0.7584(13) 0.9879(3) 0.0326(5) Uiso 1.000000 GR
C3 C 0.4311(3) 0.7089(2) 0.68275(17) 0.0159(3) Uani 1.000000 .


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
O2 C4 1.4534(17) . ?
O2 C2 1.3285(17) . ?
O4 C5 1.4551(16) . ?
O4 C3 1.3263(17) . ?
O3 C3 1.1996(17) . ?
O1 C2 1.2016(17) . ?
C4 H4a 0.9800 . ?
C4 H4b 0.9800 . ?
C4 H4c 0.9800 . ?
C2 C1 1.5030(19) . ?
C1 C1 1.332(3) 2_666 ?
C1 C3 1.5072(19) . ?
C5 H5a 0.9800 . ?
C5 H5b 0.9800 . ?
C5 H5c 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 O2 C4 115.38(11) . . ?
C3 O4 C5 115.08(11) . . ?
H4a C4 O2 109.5 . . ?
H4b C4 O2 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 O2 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
O1 C2 O2 125.62(13) . . ?
C1 C2 O2 110.16(11) . . ?
C1 C2 O1 124.22(13) . . ?
C1 C1 C2 120.51(16) 2_666 . ?
C3 C1 C2 116.32(12) . . ?
H5a C5 O4 109.5 . . ?
H5b C5 O4 109.5 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 O4 109.5 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
O3 C3 O4 125.92(13) . . ?
C1 C3 O4 111.74(11) . . ?
C1 C3 O3 122.28(13) . . ?

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
O2 C2 C1 C1 168.50(14) . . . 2_666 ?
O2 C2 C1 C3 -14.81(13) . . . . ?
O4 C3 C1 C2 92.05(12) . . . . ?
O4 C3 C1 C1 -91.35(14) . . . 2_666 ?
O3 C3 C1 C2 -85.32(14) . . . . ?
O3 C3 C1 C1 91.28(17) . . . 2_666 ?
O1 C2 C1 C1 -11.98(17) . . . 2_666 ?
O1 C2 C1 C3 164.71(14) . . . . ?
C2 C1 C1 C2 180.00(17) . . 2_666 2_666 ?
C2 C1 C1 C3 -3.54(17) . . 2_666 2_666 ?


_olex2_submission_special_instructions 'No special instructions were received'
