# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_21bh011_cd_c
_database_code_depnum_ccdc_archive 'CCDC 2155506'
loop_
_audit_author_name
_audit_author_address
'Hawkins B.A.'
;Sydney Pharmacy School, Faculty of Medicine and Health, The University of Sydney
Australia
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 O5, H2 O'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         252.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   6.6514(3)
_cell_length_b                   7.1118(3)
_cell_length_c                   12.5709(3)
_cell_angle_alpha                103.594(3)
_cell_angle_beta                 96.171(3)
_cell_angle_gamma                98.824(4)
_cell_volume                     564.73(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9367
_cell_measurement_temperature    139(20)
_cell_measurement_theta_max      40.2340
_cell_measurement_theta_min      3.0200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -1 -3 0.2835
0 10 -3 0.0672
1 -9 -3 0.0612
0 9 3 0.0639
2 -7 -9 0.0620
-4 7 9 0.1275
-9 1 3 0.2491
2 -2 -16 0.0700
-7 2 12 0.1853
-8 0 10 0.2134
2 4 -17 0.0732
-3 -6 15 0.1341
1 10 -8 0.0714
2 9 -8 0.1000
-1 -10 8 0.0746
0 7 8 0.0640
1 -7 -8 0.0592
0 2 16 0.0623
1 -2 -16 0.0596
1 1 -18 0.0612
0 -1 17 0.0639

_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.139
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
9.3508 -0.9732 -3.0038 -0.0006 0.0091 1.0000
-0.4502 9.9123 -2.5489 0.7937 -0.6083 0.0090
1.4928 -9.1257 -3.3076 -0.9355 0.3305 0.1250
-0.2434 9.0759 2.9079 0.9428 -0.3332 0.0090
1.9790 -7.3881 -8.5765 -0.9789 0.0248 0.2026
-4.0862 7.0330 8.6747 0.9031 -0.0227 -0.4288
-9.3435 0.9644 3.2252 0.0090 0.0008 -1.0000
2.1671 -2.1543 -15.9020 -0.7925 -0.5457 0.2723
-6.9700 1.9520 12.3575 0.5225 0.3606 -0.7726
-8.1807 0.3181 10.2663 0.2611 0.3424 -0.9025
1.7332 3.7702 -17.4175 -0.3215 -0.9105 0.2601
-3.4428 -5.6500 15.2282 0.0224 0.8958 -0.4440
0.7359 9.5361 -8.1146 0.5605 -0.8142 0.1516
2.1709 9.0541 -8.3125 0.5406 -0.7850 0.3026
-0.6700 -9.5526 8.1009 -0.5611 0.8150 -0.1446
0.3045 7.3138 7.9676 0.9988 -0.0255 0.0420
0.9496 -7.4114 -8.3592 -0.9954 0.0256 0.0922
0.3056 1.9941 15.6644 0.8238 0.5669 -0.0092
0.9832 -2.0984 -15.9262 -0.8150 -0.5607 0.1467
0.7569 0.9931 -17.5309 -0.6021 -0.7855 0.1430
0.4996 -1.1271 17.2880 0.6083 0.7937 -0.0092

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.999
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139(20)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  28.20   0.30    7.50    --    1.09 -57.00-180.00  334
  2  ω    -11.00  91.00   0.30    7.50    --   18.00  60.00  13.45  340
  3  ω     -3.00  99.00   0.30    7.50    --   26.00  59.00 119.13  340
  4  ω      2.00 102.20   0.30    7.50    --   30.00  58.00 -88.60  334
  5  ω    -34.00  66.20   0.30   30.00    --   38.00 -59.00 -41.19  334
  6  ω   -135.00 -34.80   0.30   30.00    --  -62.64 -59.00-156.86  334
  7  ω    -92.00  10.00   0.30   30.00    --  -62.64  60.00-179.79  340
  8  ω   -135.00 -34.80   0.30   30.00    --  -62.64 -58.00-126.98  334
  9  ω   -135.00 -34.80   0.30   30.00    --  -62.64 -57.00 -90.00  334
 10  ω    -92.00  10.00   0.30   30.00    --  -62.64  60.00 -37.36  340
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224651000
_diffrn_orient_matrix_UB_12      0.0915057000
_diffrn_orient_matrix_UB_13      0.0405010000
_diffrn_orient_matrix_UB_21      0.0093786000
_diffrn_orient_matrix_UB_22      -0.0500422000
_diffrn_orient_matrix_UB_23      0.0423758000
_diffrn_orient_matrix_UB_31      0.1063921000
_diffrn_orient_matrix_UB_32      0.0048929000
_diffrn_orient_matrix_UB_33      -0.0032862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2461
_reflns_number_total             2799
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.046
_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)+(0.0639P)²+0.1208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O4 O 0.82431(10) 0.29226(11) 0.52823(6) 0.01738(17) Uani 1 1 d . . . . .
O1 O 0.43707(11) 0.18946(11) 0.81047(6) 0.01763(18) Uani 1 1 d . . . . .
O2 O 0.76966(11) 0.32864(12) 0.86877(6) 0.02081(19) Uani 1 1 d . . . . .
O5 O 0.49143(13) 0.30314(13) 0.17674(6) 0.0244(2) Uani 1 1 d . . . . .
O3 O 0.99627(11) 0.30765(13) 0.69039(6) 0.0233(2) Uani 1 1 d . . . . .
O1' O 0.84356(13) 0.39638(13) 0.10914(7) 0.0259(2) Uani 1 1 d . . . . .
C7 C 0.45462(15) 0.24061(14) 0.49343(8) 0.0146(2) Uani 1 1 d . . . . .
C8 C 0.45154(15) 0.23388(14) 0.60561(8) 0.0146(2) Uani 1 1 d . . . . .
C3 C 0.62424(15) 0.26369(14) 0.79491(8) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.66627(16) 0.29586(15) 0.35240(8) 0.0171(2) Uani 1 1 d . . . . .
C4 C 0.62896(15) 0.25914(14) 0.67645(8) 0.0146(2) Uani 1 1 d . . . . .
C11 C 0.29259(16) 0.23834(16) 0.31137(9) 0.0193(2) Uani 1 1 d . . . . .
C6 C 0.64588(14) 0.27510(14) 0.45794(8) 0.0148(2) Uani 1 1 d . . . . .
C5 C 0.82763(15) 0.28829(15) 0.63820(8) 0.0161(2) Uani 1 1 d . . . . .
C12 C 0.27625(15) 0.22116(15) 0.41709(8) 0.0174(2) Uani 1 1 d . . . . .
C10 C 0.48759(16) 0.27871(15) 0.27937(8) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.40804(16) 0.19819(16) 0.92453(8) 0.0177(2) Uani 1 1 d . . . . .
C1 C 0.18990(17) 0.10242(18) 0.92278(9) 0.0230(2) Uani 1 1 d . . . . .
H1A H 0.092(3) 0.163(3) 0.8841(14) 0.039(4) Uiso 1 1 d . . . . .
H1B H 0.161(2) 0.118(2) 1.0009(13) 0.034(4) Uiso 1 1 d . . . . .
H1C H 0.167(2) -0.040(2) 0.8861(12) 0.024(3) Uiso 1 1 d . . . . .
H1'A H 0.830(3) 0.381(3) 0.0400(17) 0.047(5) Uiso 1 1 d . . . . .
H1'B H 0.932(3) 0.494(3) 0.1409(16) 0.046(5) Uiso 1 1 d . . . . .
H2A H 0.508(2) 0.128(2) 0.9558(11) 0.022(3) Uiso 1 1 d . . . . .
H2B H 0.434(2) 0.338(2) 0.9644(11) 0.019(3) Uiso 1 1 d . . . . .
H12 H 0.142(2) 0.198(2) 0.4408(12) 0.022(3) Uiso 1 1 d . . . . .
H9 H 0.801(2) 0.322(2) 0.3313(13) 0.032(4) Uiso 1 1 d . . . . .
H11 H 0.175(2) 0.227(2) 0.2603(12) 0.026(3) Uiso 1 1 d . . . . .
H8 H 0.323(2) 0.215(2) 0.6333(11) 0.020(3) Uiso 1 1 d . . . . .
H5 H 0.615(4) 0.340(3) 0.1657(18) 0.064(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C6 1.3725(12) . ?
O4 C5 1.3872(11) . ?
O1 C3 1.3290(12) . ?
O1 C2 1.4555(11) . ?
O2 C3 1.2162(12) . ?
O5 C10 1.3440(12) . ?
O5 H5 0.86(2) . ?
O3 C5 1.2082(12) . ?
O1' H1'A 0.84(2) . ?
O1' H1'B 0.83(2) . ?
C7 C8 1.4245(13) . ?
C7 C6 1.3983(13) . ?
C7 C12 1.4107(13) . ?
C8 C4 1.3608(13) . ?
C8 H8 0.959(14) . ?
C3 C4 1.4857(13) . ?
C9 C6 1.3874(13) . ?
C9 C10 1.3923(14) . ?
C9 H9 0.966(16) . ?
C4 C5 1.4560(13) . ?
C11 C12 1.3771(14) . ?
C11 C10 1.4067(15) . ?
C11 H11 0.937(15) . ?
C12 H12 0.971(14) . ?
C2 C1 1.5008(14) . ?
C2 H2A 0.995(14) . ?
C2 H2B 0.981(14) . ?
C1 H1A 0.981(17) . ?
C1 H1B 1.004(16) . ?
C1 H1C 0.988(15) . ?

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
C6 O4 C5 122.99(8) . . ?
C3 O1 C2 116.24(8) . . ?
C10 O5 H5 111.5(15) . . ?
H1'A O1' H1'B 110.9(19) . . ?
C6 C7 C8 118.06(9) . . ?
C6 C7 C12 118.08(9) . . ?
C12 C7 C8 123.83(9) . . ?
C7 C8 H8 120.2(8) . . ?
C4 C8 C7 121.26(9) . . ?
C4 C8 H8 118.5(8) . . ?
O1 C3 C4 110.77(8) . . ?
O2 C3 O1 123.92(9) . . ?
O2 C3 C4 125.30(9) . . ?
C6 C9 C10 117.97(9) . . ?
C6 C9 H9 120.4(9) . . ?
C10 C9 H9 121.7(9) . . ?
C8 C4 C3 120.77(9) . . ?
C8 C4 C5 120.51(9) . . ?
C5 C4 C3 118.69(8) . . ?
C12 C11 C10 120.15(9) . . ?
C12 C11 H11 121.0(9) . . ?
C10 C11 H11 118.8(9) . . ?
O4 C6 C7 120.53(8) . . ?
O4 C6 C9 116.81(8) . . ?
C9 C6 C7 122.65(9) . . ?
O4 C5 C4 116.53(8) . . ?
O3 C5 O4 115.58(9) . . ?
O3 C5 C4 127.88(9) . . ?
C7 C12 H12 118.9(8) . . ?
C11 C12 C7 120.30(9) . . ?
C11 C12 H12 120.7(8) . . ?
O5 C10 C9 122.42(10) . . ?
O5 C10 C11 116.74(9) . . ?
C9 C10 C11 120.82(9) . . ?
O1 C2 C1 107.39(8) . . ?
O1 C2 H2A 108.2(8) . . ?
O1 C2 H2B 107.0(8) . . ?
C1 C2 H2A 111.7(8) . . ?
C1 C2 H2B 111.2(8) . . ?
H2A C2 H2B 111.1(11) . . ?
C2 C1 H1A 111.5(10) . . ?
C2 C1 H1B 109.1(9) . . ?
C2 C1 H1C 110.9(8) . . ?
H1A C1 H1B 108.4(13) . . ?
H1A C1 H1C 108.7(13) . . ?
H1B C1 H1C 108.1(12) . . ?

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 C3 C4 C8 16.72(13) . . . . ?
O1 C3 C4 C5 -165.14(9) . . . . ?
O2 C3 C4 C8 -162.26(10) . . . . ?
O2 C3 C4 C5 15.88(15) . . . . ?
C7 C8 C4 C3 176.33(8) . . . . ?
C7 C8 C4 C5 -1.77(15) . . . . ?
C8 C7 C6 O4 3.09(14) . . . . ?
C8 C7 C6 C9 -176.14(9) . . . . ?
C8 C7 C12 C11 177.01(9) . . . . ?
C8 C4 C5 O4 1.16(14) . . . . ?
C8 C4 C5 O3 -178.03(10) . . . . ?
C3 O1 C2 C1 -178.46(9) . . . . ?
C3 C4 C5 O4 -176.98(8) . . . . ?
C3 C4 C5 O3 3.83(16) . . . . ?
C6 O4 C5 O3 -179.07(9) . . . . ?
C6 O4 C5 C4 1.64(14) . . . . ?
C6 C7 C8 C4 -0.34(15) . . . . ?
C6 C7 C12 C11 -0.76(15) . . . . ?
C6 C9 C10 O5 177.67(9) . . . . ?
C6 C9 C10 C11 -1.03(16) . . . . ?
C5 O4 C6 C7 -3.82(15) . . . . ?
C5 O4 C6 C9 175.45(9) . . . . ?
C12 C7 C8 C4 -178.11(9) . . . . ?
C12 C7 C6 O4 -179.01(8) . . . . ?
C12 C7 C6 C9 1.76(15) . . . . ?
C12 C11 C10 O5 -176.77(9) . . . . ?
C12 C11 C10 C9 1.99(16) . . . . ?
C10 C9 C6 O4 179.88(9) . . . . ?
C10 C9 C6 C7 -0.87(16) . . . . ?
C10 C11 C12 C7 -1.06(16) . . . . ?
C2 O1 C3 O2 3.21(14) . . . . ?
C2 O1 C3 C4 -175.79(8) . . . . ?

_olex2_submission_original_sample_id EN09-hydrate
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.726
####################################################################### 
# 
# 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_21bh009_cd
_database_code_depnum_ccdc_archive 'CCDC 2155508'
loop_
_audit_author_name
_audit_author_address
'Hawkins B.A.'
;Sydney Pharmacy School, Faculty of Medicine and Health, The University of Sydney
Australia
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 N2 H6'
_chemical_formula_sum            'C4 N2 H6'
_chemical_formula_weight         82.10
_chemical_absolute_configuration ?
_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'
N N 0.0061 0.0033 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.0180(2)
_cell_length_b                   8.1483(4)
_cell_length_c                   9.6871(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     475.02(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14451
_cell_measurement_temperature    120.1(3)
_cell_measurement_theta_max      51.4350
_cell_measurement_theta_min      3.9710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             176
_exptl_crystal_preparation       'Used as purchased'
_exptl_crystal_recrystallization_method n/a
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            2246
_diffrn_reflns_point_group_measured_fraction_full 0.614
_diffrn_reflns_point_group_measured_fraction_max 0.566
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.276
_diffrn_reflns_theta_min         3.267
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.1(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_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    -10.00  91.00   1.00   10.00    --   18.00  57.00 -17.36  101
  2  ω    -11.00  91.00   1.00   10.00    --   18.00  60.00  87.62  102
  3  ω     -6.00  95.00   1.00   10.00    --   22.00  56.00 170.81  101
  4  ω     -3.00  99.00   1.00   10.00    --   26.00  60.00 -98.85  102
  5  ω    -30.00  71.00   1.00   92.50    --   42.00 -60.00 101.93  101
  6  ω   -135.00 -34.00   1.00   92.50    --  -62.64 -57.00  90.00  101
  7  ω   -135.00 -34.00   1.00   92.50    --  -62.64 -60.00-177.13  101
  8  ω   -135.00 -34.00   1.00   92.50    --  -62.64 -57.00  60.00  101
  9  ω   -135.00 -34.00   1.00   92.50    --  -62.64 -60.00 123.13  101
 10  ω     37.00 138.00   1.00   92.50    --   64.83  57.00-180.00  101
 11  ω     36.00 138.00   1.00   92.50    --   64.83  59.00-106.48  102
 12  ω     36.00 138.00   1.00   92.50    --   64.83  60.00  20.88  102
 13  ω     37.00 138.00   1.00   92.50    --   64.83  57.00 120.00  101
 14  ω     -8.00  94.00   1.00   92.50    --   64.83 -60.00 -89.96  102
 15  ω     -8.00  94.00   1.00   92.50    --   64.83 -60.00  85.89  102
 16  ω     -8.00  93.00   1.00   92.50    --   64.83 -59.00 122.96  101
 17  ω     -8.00  94.00   1.00   92.50    --   64.83 -60.00 172.87  102
 18  ω     37.00 138.00   1.00   92.50    --   64.83  57.00 -30.00  101
 19  ω     37.00 138.00   1.00   92.50    --   64.83  57.00  60.00  101
 20  ω     37.00 138.00   1.00   92.50    --   64.83  57.00 -60.00  101
 21  ω     -8.00  42.00   1.00   92.50    --   64.83 -60.00  49.06   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0695656000
_diffrn_orient_matrix_UB_12      -0.0003442000
_diffrn_orient_matrix_UB_13      0.0591167000
_diffrn_orient_matrix_UB_21      -0.0767032000
_diffrn_orient_matrix_UB_22      0.0514046000
_diffrn_orient_matrix_UB_23      0.0349818000
_diffrn_orient_matrix_UB_31      -0.0563737000
_diffrn_orient_matrix_UB_32      -0.0702294000
_diffrn_orient_matrix_UB_33      0.0253285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1947
_reflns_number_total             2246
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     52.01
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.042
_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)+(0.1027P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C4'-H4'B
 1.059 with sigma of 0.02
 C4'-H4'C
 1.059 with sigma of 0.02
 C4'-H4'A
 1.059 with sigma of 0.02
 C2'-H2'
 1.083 with sigma of 0.02
 C1'-H1'
 1.083 with sigma of 0.02
 N1'-H1'A
 1.009 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
C2' C 0.51481(12) 0.36390(11) 0.51297(8) 0.02266(14) Uani 1 1 d D . . . .
C1' C 0.53340(14) 0.35133(12) 0.65318(8) 0.02553(15) Uani 1 1 d D . . . .
C3' C 0.79186(11) 0.51679(9) 0.58602(7) 0.01885(11) Uani 1 1 d . . . . .
C4' C 0.98521(16) 0.62993(13) 0.58156(11) 0.03073(18) Uani 1 1 d D . . . .
N1' N 0.68020(10) 0.46928(8) 0.47196(6) 0.01884(11) Uani 1 1 d D . . . .
N2' N 0.70728(12) 0.44814(10) 0.69853(6) 0.02291(13) Uani 1 1 d . . . . .
H4'B H 1.021(6) 0.711(4) 0.663(3) 0.115(11) Uiso 1 1 d D . . . .
H4'C H 0.948(4) 0.716(3) 0.503(3) 0.078(8) Uiso 1 1 d D . . . .
H4'A H 1.130(5) 0.575(6) 0.620(5) 0.161(17) Uiso 1 1 d D . . . .
H2' H 0.413(3) 0.315(2) 0.4357(17) 0.040(5) Uiso 1 1 d D . . . .
H1' H 0.453(3) 0.272(2) 0.7229(16) 0.038(4) Uiso 1 1 d D . . . .
H1'A H 0.715(4) 0.502(3) 0.3777(16) 0.065(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2' C1' 1.3666(11) . ?
C2' N1' 1.3732(10) . ?
C2' H2' 1.046(14) . ?
C1' N2' 1.3822(10) . ?
C1' H1' 1.051(14) . ?
C3' C4' 1.4852(11) . ?
C3' N1' 1.3499(9) . ?
C3' N2' 1.3266(9) . ?
C4' H4'B 1.052(19) . ?
C4' H4'C 1.062(17) . ?
C4' H4'A 1.046(19) . ?
N1' H1'A 0.975(15) . ?

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
C1' C2' N1' 105.97(7) . . ?
C1' C2' H2' 137.0(11) . . ?
N1' C2' H2' 117.1(11) . . ?
C2' C1' N2' 109.58(7) . . ?
C2' C1' H1' 130.3(10) . . ?
N2' C1' H1' 119.6(9) . . ?
N1' C3' C4' 122.97(7) . . ?
N2' C3' C4' 125.89(7) . . ?
N2' C3' N1' 111.13(6) . . ?
C3' C4' H4'B 122(2) . . ?
C3' C4' H4'C 105.3(14) . . ?
C3' C4' H4'A 112(3) . . ?
H4'B C4' H4'C 100(3) . . ?
H4'B C4' H4'A 80(3) . . ?
H4'C C4' H4'A 136(3) . . ?
C2' N1' H1'A 126.9(14) . . ?
C3' N1' C2' 107.66(6) . . ?
C3' N1' H1'A 125.5(14) . . ?
C3' N2' C1' 105.66(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
C2' C1' N2' C3' -0.35(10) . . . . ?
C1' C2' N1' C3' -0.08(9) . . . . ?
C4' C3' N1' C2' 179.19(8) . . . . ?
C4' C3' N2' C1' -179.01(9) . . . . ?
N1' C2' C1' N2' 0.26(10) . . . . ?
N1' C3' N2' C1' 0.30(9) . . . . ?
N2' C3' N1' C2' -0.14(9) . . . . ?

_olex2_exptl_crystal_mounting_method Paratone-N
_olex2_submission_original_sample_id 2mim
_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 6.154
_oxdiff_exptl_absorpt_empirical_full_min 0.249
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2155507'
loop_
_audit_author_name
_audit_author_address
'Hawkins B.A.'
;Sydney Pharmacy School, Faculty of Medicine and Health, The University of Sydney
Australia
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O5'
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H16 N2 O5'
_chemical_oxdiff_usercomment     ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.51259(18)
_cell_length_b                   9.8167(3)
_cell_length_c                   11.1108(2)
_cell_angle_alpha                73.303(2)
_cell_angle_beta                 82.2052(17)
_cell_angle_gamma                77.655(2)
_cell_volume                     764.30(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    36450
_cell_measurement_temperature    120.0(3)
_cell_measurement_theta_max      65.1460
_cell_measurement_theta_min      3.1620
_cell_oxdiff_angle_alpha         73.303(2)
_cell_oxdiff_angle_beta          82.2052(17)
_cell_oxdiff_angle_gamma         77.655(2)
_cell_oxdiff_length_a            7.51259(18)
_cell_oxdiff_length_b            9.8167(3)
_cell_oxdiff_length_c            11.1108(2)
_cell_oxdiff_measurement_reflns_used 36450
_cell_oxdiff_volume              764.30(3)
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.348
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 9 5 0.1959
-1 9 13 0.0999
0 -12 -11 0.1147
-1 2 15 0.1135
1 8 15 0.0718
1 0 -15 0.1000
-1 -7 -15 0.0914
-2 0 -15 0.0951
1 -6 11 0.1261
-5 2 -13 0.1419
0 -13 2 0.1283
-7 7 -4 0.1855
1 -13 -4 0.1376
-7 8 5 0.1732
9 -1 -7 0.2295
7 0 -10 0.1885
-4 8 11 0.1256
1 -9 -13 0.1257
2 2 -14 0.1048
0 7 15 0.0742
-3 -14 -5 0.1147
-1 5 -12 0.1047
3 8 15 0.0934
6 9 13 0.1276
4 13 7 0.1371

_exptl_crystal_preparation       'Slow evaporation from DCM'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.16
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
9.1644 9.2427 5.1400 0.2024 -0.6839 0.7009
-1.4054 9.0198 13.1536 -0.7602 0.0188 0.6494
-0.1447 -11.8192 -10.9772 0.5220 -0.0125 -0.8529
-0.5784 2.3312 15.3253 -0.9431 -0.2802 0.1790
0.6400 7.6632 14.8444 -0.7921 -0.2358 0.5630
1.1086 0.2691 -14.6646 0.9586 0.2846 0.0090
-0.5281 -7.2101 -15.0017 0.8125 0.2418 -0.5305
-2.0900 0.4561 -14.7180 0.8238 0.5669 0.0090
0.7586 -6.1610 11.3470 -0.7464 -0.5131 -0.4239
-4.7271 2.2029 -12.6730 0.6037 0.7875 0.1244
-0.2080 -12.6337 1.5893 -0.2679 -0.3479 -0.8984
-7.1864 6.6752 -4.1154 0.0235 0.8971 0.4412
1.1377 -13.1201 -3.5332 0.1017 -0.3462 -0.9326
-6.6312 8.4044 4.5073 -0.4632 0.6742 0.5753
8.8473 -0.5493 -6.6639 0.7937 -0.6083 -0.0092
6.8352 -0.3786 -10.4714 0.9428 -0.3332 -0.0092
-3.9032 8.4258 11.2153 -0.7577 0.2685 0.5948
1.4391 -8.9734 -13.1667 0.7631 -0.0202 -0.6460
1.5108 2.3957 -13.7342 0.9458 0.2809 0.1629
0.4681 7.0082 15.0610 -0.8214 -0.2433 0.5159
-2.7174 -13.8263 -4.6354 -0.0086 -0.0036 -1.0000
-1.0831 4.9527 -12.3026 0.7758 0.5343 0.3356
3.3393 8.3278 14.5346 -0.6459 -0.4438 0.6212
5.5705 9.1536 12.9940 -0.4421 -0.5759 0.6876
4.4703 13.2703 7.2238 -0.0815 -0.2280 0.9702

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12517
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.294
_diffrn_reflns_theta_min         2.507
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4948
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00   0.00  101
  2  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00 -60.00  101
  3  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00-120.00  101
  4  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00  30.00  101
  5  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00-150.00  101
  6  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00 150.00  101
  7  ω   -115.00 -14.00   1.00   15.00    --  -42.13 -57.00  90.00  101
  8  ω     14.00 115.00   1.00   15.00    --   42.13  57.00 -60.00  101
  9  ω    -30.00  70.00   1.00   15.00    --   42.13 -57.00 -90.00  100
 10  ω    -30.00  70.00   1.00   15.00    --   42.13 -57.00 150.00  100
 11  ω    -30.00  71.00   1.00   15.00    --   42.13 -60.00   4.22  101
 12  ω     62.00 158.00   1.00   60.00    --   90.50  59.00 -66.45   96
 13  ω     62.00 158.00   1.00   60.00    --   90.50  59.00  68.63   96
 14  ω     62.00 158.00   1.00   60.00    --   90.50  59.00  25.66   96
 15  ω     63.00 158.00   1.00   60.00    --   90.50  56.00 -41.05   95
 16  ω     62.00 158.00   1.00   60.00    --   90.50  59.00  -7.79   96
 17  ω     63.00 158.00   1.00   60.00    --   90.50  56.00  61.37   95
 18  ω     62.00 158.00   1.00   60.00    --   90.50  60.00 -54.78   96
 19  ω     62.00 158.00   1.00   60.00    --   90.50  60.00  42.57   96
 20  ω     62.00 158.00   1.00   60.00    --   90.50  58.00 -15.77   96
 21  ω     62.00 158.00   1.00   60.00    --   90.50  59.00  81.58   96
 22  ω     63.00 158.00   1.00   60.00    --   90.50  55.00 133.31   95
 23  ω     62.00 158.00   1.00   60.00    --   90.50  57.00-155.76   96
 24  ω     62.00 158.00   1.00   60.00    --   90.50  58.00  10.91   96
 25  ω     63.00 158.00   1.00   60.00    --   90.50  56.00 -81.53   95
 26  ω     63.00 158.00   1.00   60.00    --   90.50  56.00 102.72   95
 27  ω     62.00 158.00   1.00   60.00    --   90.50  58.00-176.20   96
 28  ω     62.00 158.00   1.00   60.00    --   90.50  58.00-143.98   96
 29  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00-157.52  102
 30  ω     62.00 158.00   1.00   60.00    --   90.50  57.00-118.90   96
 31  ω     63.00 158.00   1.00   60.00    --   90.50  55.00 176.76   95
 32  ω     62.00 158.00   1.00   60.00    --   90.50  60.00-108.03   96
 33  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00 -95.91  102
 34  ω     62.00 158.00   1.00   60.00    --   90.50  60.00 153.08   96
 35  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00  16.74  102
 36  ω     62.00 158.00   1.00   60.00    --   90.50  59.00 114.30   96
 37  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00  48.89  102
 38  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00 -50.51  102
 39  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00  95.00  102
 40  ω     17.00 119.00   1.00   60.00    --   90.50 -60.00 146.57  102
 41  ω     62.00 158.00   1.00   60.00    --   90.50  60.00 144.32   96
 42  ω    -70.00  31.00   1.00   15.00    --  -42.13  57.00-120.00  101
 43  ω   -115.00 -16.00   1.00   15.00    --  -42.13 -44.00  25.39   99
 44  ω   -116.00 -17.00   1.00   15.00    --  -42.13 -42.00 162.63   99
 45  ω     14.00 115.00   1.00   15.00    --   42.13  57.00-120.00  101
 46  ω     14.00 115.00   1.00   15.00    --   42.13  57.00 150.00  101
 47  ω    -30.00  70.00   1.00   15.00    --   42.13 -57.00-180.00  100
 48  ω     14.00 115.00   1.00   15.00    --   42.13  57.00 120.00  101
 49  ω     14.00  93.00   1.00   15.00    --   42.13  57.00-150.00   79
 50  ω     14.00 115.00   1.00   15.00    --   42.13  57.00  60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0439379000
_diffrn_orient_matrix_UB_12      0.0127079000
_diffrn_orient_matrix_UB_13      -0.0618146000
_diffrn_orient_matrix_UB_21      -0.0863282000
_diffrn_orient_matrix_UB_22      0.0257591000
_diffrn_orient_matrix_UB_23      -0.0254584000
_diffrn_orient_matrix_UB_31      0.0041386000
_diffrn_orient_matrix_UB_32      0.0711713000
_diffrn_orient_matrix_UB_33      0.0010086000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10519
_reflns_number_total             12517
_reflns_odcompleteness_completeness 97.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     45.18
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         12517
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+0.0335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C9-H9
 1.083 with sigma of 0.02
 C11-H11
 1.083 with sigma of 0.02
 C12-H12
 1.083 with sigma of 0.02
 C1-H1A
 1.059 with sigma of 0.02
 C1-H1B
 1.059 with sigma of 0.02
 C1-H1C
 1.059 with sigma of 0.02
 C4'-H4'A
 1.059 with sigma of 0.02
 C4'-H4'B
 1.059 with sigma of 0.02
 C4'-H4'C
 1.059 with sigma of 0.02
 C1'-H1'
 1.083 with sigma of 0.02
 C2'-H2'
 1.083 with sigma of 0.02
 N1'-H1'A
 1.009 with sigma of 0.02
 O5-H5
 0.967 with sigma of 0.02
 C2-H2A
 1.092 with sigma of 0.02
 C2-H2B
 1.092 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
C1 C 0.76273(7) 0.80094(6) 1.28835(5) 0.02617(8) Uani 1 1 d D . . . .
C1' C 0.22705(6) 0.91577(4) 0.20107(4) 0.02167(6) Uani 1 1 d D . . . .
C2' C 0.13640(6) 1.03331(5) 0.11860(3) 0.02073(6) Uani 1 1 d D . . . .
C2 C 0.80980(6) 0.64882(5) 1.27551(4) 0.02161(6) Uani 1 1 d D . . . .
C3' C 0.13163(5) 1.08024(4) 0.30188(3) 0.01601(5) Uani 1 1 d . . . . .
C3 C 0.79543(5) 0.53340(4) 1.11806(3) 0.01524(5) Uani 1 1 d . . . . .
C4 C 0.72039(4) 0.54859(4) 0.99717(3) 0.01425(5) Uani 1 1 d . . . . .
C4' C 0.09839(6) 1.16383(4) 0.39786(4) 0.02042(6) Uani 1 1 d D . . . .
C5 C 0.76992(5) 0.42832(4) 0.93918(3) 0.01507(5) Uani 1 1 d . . . . .
C6 C 0.59632(4) 0.57534(3) 0.76358(3) 0.01408(5) Uani 1 1 d . . . . .
C7 C 0.54696(4) 0.69121(4) 0.81881(3) 0.01470(5) Uani 1 1 d . . . . .
C8 C 0.61236(4) 0.67393(4) 0.93742(3) 0.01500(5) Uani 1 1 d . . . . .
C9 C 0.54109(5) 0.58160(4) 0.64784(3) 0.01629(5) Uani 1 1 d D . . . .
C10 C 0.43168(5) 0.70923(4) 0.58327(3) 0.01660(5) Uani 1 1 d . . . . .
C11 C 0.38191(5) 0.82867(4) 0.63610(3) 0.01881(6) Uani 1 1 d D . . . .
C12 C 0.43795(5) 0.81861(4) 0.75188(3) 0.01809(6) Uani 1 1 d D . . . .
N1' N 0.07634(4) 1.13593(3) 0.18421(3) 0.01752(5) Uani 1 1 d D . . . .
N2' N 0.22320(5) 0.94583(4) 0.31590(3) 0.01893(5) Uani 1 1 d . . . . .
O1 O 0.73592(4) 0.65075(3) 1.16033(3) 0.01922(5) Uani 1 1 d . . . . .
O2 O 0.90094(4) 0.42887(3) 1.17290(3) 0.02021(5) Uani 1 1 d . . . . .
O3 O 0.86304(5) 0.31097(3) 0.98029(3) 0.02110(5) Uani 1 1 d . . . . .
O4 O 0.70256(4) 0.44903(3) 0.82413(2) 0.01611(4) Uani 1 1 d . . . . .
O5 O 0.37666(5) 0.71225(3) 0.47332(3) 0.02208(6) Uani 1 1 d D . . . .
H1A H 0.8237(15) 0.8705(11) 1.2172(10) 0.041(3) Uiso 1 1 d D . . . .
H1B H 0.8092(14) 0.8029(12) 1.3668(9) 0.038(2) Uiso 1 1 d D . . . .
H1C H 0.6279(13) 0.8366(12) 1.2949(10) 0.040(3) Uiso 1 1 d D . . . .
H2A H 0.9449(12) 0.6118(10) 1.2693(9) 0.030(2) Uiso 1 1 d D . . . .
H2B H 0.7547(12) 0.5787(10) 1.3455(8) 0.027(2) Uiso 1 1 d D . . . .
H5 H 0.3205(18) 0.8103(12) 0.4263(12) 0.059(3) Uiso 1 1 d D . . . .
H8 H 0.5774(13) 0.7593(11) 0.9737(9) 0.029(2) Uiso 1 1 d . . . . .
H9 H 0.5848(12) 0.4927(9) 0.6159(8) 0.026(2) Uiso 1 1 d D . . . .
H11 H 0.3063(12) 0.9175(10) 0.5874(9) 0.028(2) Uiso 1 1 d D . . . .
H12 H 0.4033(14) 0.9042(11) 0.7895(10) 0.036(2) Uiso 1 1 d D . . . .
H1' H 0.2917(13) 0.8192(10) 0.1905(10) 0.036(2) Uiso 1 1 d D . . . .
H2' H 0.1118(15) 1.0561(12) 0.0288(9) 0.041(3) Uiso 1 1 d D . . . .
H1'A H 0.0045(14) 1.2253(10) 0.1558(10) 0.038(3) Uiso 1 1 d D . . . .
H4'A H 0.0470(13) 1.1128(10) 0.4781(8) 0.030(2) Uiso 1 1 d D . . . .
H4'B H 0.0119(14) 1.2567(11) 0.3707(10) 0.039(3) Uiso 1 1 d D . . . .
H4'C H 0.2128(14) 1.1878(12) 0.4130(10) 0.040(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5028(6) . ?
C1 H1A 1.014(10) . ?
C1 H1B 0.988(10) . ?
C1 H1C 0.999(10) . ?
C1' C2' 1.3640(5) . ?
C1' N2' 1.3850(5) . ?
C1' H1' 1.000(9) . ?
C2' N1' 1.3742(5) . ?
C2' H2' 0.991(10) . ?
C2 O1 1.4562(4) . ?
C2 H2A 1.002(9) . ?
C2 H2B 0.988(8) . ?
C3' C4' 1.4886(5) . ?
C3' N1' 1.3492(4) . ?
C3' N2' 1.3272(5) . ?
C3 C4 1.4828(4) . ?
C3 O1 1.3346(4) . ?
C3 O2 1.2151(4) . ?
C4 C5 1.4601(5) . ?
C4 C8 1.3650(4) . ?
C4' H4'A 0.963(9) . ?
C4' H4'B 0.993(10) . ?
C4' H4'C 0.985(9) . ?
C5 O3 1.2103(4) . ?
C5 O4 1.3833(4) . ?
C6 C7 1.4025(5) . ?
C6 C9 1.3849(4) . ?
C6 O4 1.3675(4) . ?
C7 C8 1.4207(4) . ?
C7 C12 1.4074(4) . ?
C8 H8 1.002(10) . ?
C9 C10 1.4011(5) . ?
C9 H9 1.009(8) . ?
C10 C11 1.4169(5) . ?
C10 O5 1.3323(4) . ?
C11 C12 1.3777(5) . ?
C11 H11 0.988(9) . ?
C12 H12 1.014(10) . ?
N1' H1'A 0.919(9) . ?
O5 H5 0.987(11) . ?

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 H1A 112.2(6) . . ?
C2 C1 H1B 108.8(6) . . ?
C2 C1 H1C 112.1(6) . . ?
H1A C1 H1B 106.3(9) . . ?
H1A C1 H1C 110.2(9) . . ?
H1B C1 H1C 107.1(9) . . ?
C2' C1' N2' 109.42(3) . . ?
C2' C1' H1' 131.2(6) . . ?
N2' C1' H1' 119.4(6) . . ?
C1' C2' N1' 105.75(3) . . ?
C1' C2' H2' 134.3(7) . . ?
N1' C2' H2' 119.9(7) . . ?
C1 C2 H2A 112.7(5) . . ?
C1 C2 H2B 113.4(5) . . ?
O1 C2 C1 106.85(3) . . ?
O1 C2 H2A 108.9(5) . . ?
O1 C2 H2B 107.3(5) . . ?
H2A C2 H2B 107.5(8) . . ?
N1' C3' C4' 123.23(3) . . ?
N2' C3' C4' 126.34(3) . . ?
N2' C3' N1' 110.39(3) . . ?
O1 C3 C4 111.93(3) . . ?
O2 C3 C4 125.19(3) . . ?
O2 C3 O1 122.87(3) . . ?
C5 C4 C3 118.81(3) . . ?
C8 C4 C3 121.38(3) . . ?
C8 C4 C5 119.77(3) . . ?
C3' C4' H4'A 113.2(6) . . ?
C3' C4' H4'B 111.9(6) . . ?
C3' C4' H4'C 111.0(6) . . ?
H4'A C4' H4'B 106.2(8) . . ?
H4'A C4' H4'C 107.2(8) . . ?
H4'B C4' H4'C 107.0(9) . . ?
O3 C5 C4 127.59(3) . . ?
O3 C5 O4 115.47(3) . . ?
O4 C5 C4 116.93(3) . . ?
C9 C6 C7 122.74(3) . . ?
O4 C6 C7 120.29(3) . . ?
O4 C6 C9 116.98(3) . . ?
C6 C7 C8 118.21(3) . . ?
C6 C7 C12 117.73(3) . . ?
C12 C7 C8 124.05(3) . . ?
C4 C8 C7 121.55(3) . . ?
C4 C8 H8 121.9(6) . . ?
C7 C8 H8 116.5(6) . . ?
C6 C9 C10 118.54(3) . . ?
C6 C9 H9 116.7(5) . . ?
C10 C9 H9 124.8(5) . . ?
C9 C10 C11 119.90(3) . . ?
O5 C10 C9 117.71(3) . . ?
O5 C10 C11 122.39(3) . . ?
C10 C11 H11 117.8(5) . . ?
C12 C11 C10 120.15(3) . . ?
C12 C11 H11 122.1(5) . . ?
C7 C12 H12 118.8(6) . . ?
C11 C12 C7 120.95(3) . . ?
C11 C12 H12 120.2(6) . . ?
C2' N1' H1'A 126.7(6) . . ?
C3' N1' C2' 108.30(3) . . ?
C3' N1' H1'A 124.9(6) . . ?
C3' N2' C1' 106.14(3) . . ?
C3 O1 C2 115.88(3) . . ?
C6 O4 C5 123.24(3) . . ?
C10 O5 H5 112.9(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 O1 C3 166.50(4) . . . . ?
C1' C2' N1' C3' 0.44(5) . . . . ?
C2' C1' N2' C3' -0.21(5) . . . . ?
C3 C4 C5 O3 2.83(6) . . . . ?
C3 C4 C5 O4 -177.62(3) . . . . ?
C3 C4 C8 C7 177.12(3) . . . . ?
C4 C3 O1 C2 -176.99(3) . . . . ?
C4 C5 O4 C6 0.94(5) . . . . ?
C4' C3' N1' C2' 177.05(4) . . . . ?
C4' C3' N2' C1' -177.06(4) . . . . ?
C5 C4 C8 C7 -0.39(5) . . . . ?
C6 C7 C8 C4 -0.02(5) . . . . ?
C6 C7 C12 C11 0.02(6) . . . . ?
C6 C9 C10 C11 0.74(6) . . . . ?
C6 C9 C10 O5 -178.62(3) . . . . ?
C7 C6 C9 C10 0.14(6) . . . . ?
C7 C6 O4 C5 -1.37(5) . . . . ?
C8 C4 C5 O3 -179.60(4) . . . . ?
C8 C4 C5 O4 -0.05(5) . . . . ?
C8 C7 C12 C11 178.87(4) . . . . ?
C9 C6 C7 C8 -179.44(3) . . . . ?
C9 C6 C7 C12 -0.52(5) . . . . ?
C9 C6 O4 C5 178.93(3) . . . . ?
C9 C10 C11 C12 -1.24(6) . . . . ?
C10 C11 C12 C7 0.85(6) . . . . ?
C12 C7 C8 C4 -178.86(3) . . . . ?
N1' C3' N2' C1' 0.49(5) . . . . ?
N2' C1' C2' N1' -0.14(5) . . . . ?
N2' C3' N1' C2' -0.60(5) . . . . ?
O1 C3 C4 C5 -178.99(3) . . . . ?
O1 C3 C4 C8 3.48(5) . . . . ?
O2 C3 C4 C5 2.15(6) . . . . ?
O2 C3 C4 C8 -175.38(4) . . . . ?
O2 C3 O1 C2 1.90(6) . . . . ?
O3 C5 O4 C6 -179.46(3) . . . . ?
O4 C6 C7 C8 0.88(5) . . . . ?
O4 C6 C7 C12 179.79(3) . . . . ?
O4 C6 C9 C10 179.83(3) . . . . ?
O5 C10 C11 C12 178.09(4) . . . . ?


_ins_header                      
;
TITL 21BH003_CD_om75_b3_s in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073   7.512589   9.816667  11.110779  73.3031  82.2052  77.6554
ZERR    2.00   0.000185   0.000335   0.000197   0.0022   0.0017   0.0025
LATT  1
SFAC C H N O
UNIT 16 16 2 5
REM  CrysAlisPro recorded range (K): Min=119.8; max=120.3; aver:120.0
TEMP -120
SIZE 0.16 0.30 0.60
TREF
HKLF 4
END
;
_olex2_exptl_crystal_mounting_method Paratone-N
_olex2_submission_original_sample_id en092mim
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.824
