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

data_km1796-1
_database_code_depnum_ccdc_archive 'CCDC 2336546'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 Cl2 O'
_chemical_formula_sum            'C13 H16 Cl2 O'
_chemical_formula_weight         259.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H16Cl2O
_chemical_oxdiff_usercomment     KM1796.1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.89737(7)
_cell_length_b                   12.24079(6)
_cell_length_c                   22.05573(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.0661(4)
_cell_angle_gamma                90
_cell_volume                     5089.06(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    51579
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.4370
_cell_measurement_theta_min      2.3360
_shelx_estimated_absorpt_T_max   0.505
_shelx_estimated_absorpt_T_min   0.325
_exptl_absorpt_coefficient_mu    4.390
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 2 0.0901
1 -1 -2 0.1460
2 0 -1 0.0836
-2 0 -1 0.0816
-1 -1 2 0.1183
1 0 0 0.0947
-2 1 -2 0.1086
-1 0 0 0.0831
1 -1 1 0.1768
-1 -1 1 0.1246
-2 1 0 0.0860
-1 -2 0 0.1538
1 -1 0 0.1684
1 2 1 0.1300
-1 1 1 0.0741
-1 0 2 0.1007
-1 0 -1 0.0793
0 0 -1 0.0931
0 0 1 0.0950
-2 -1 -2 0.1115

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
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
-0.9992 0.9979 2.0007 0.0399 0.1870 -0.0623
0.9992 -0.9979 -2.0007 -0.0399 -0.1870 0.0623
1.9990 0.0005 -0.9998 0.0088 -0.0608 0.1619
-1.9992 0.0006 -0.9981 0.0691 -0.0554 -0.1593
-0.9995 -1.0001 1.9959 -0.1655 0.0480 -0.1035
0.9996 -0.0000 -0.0004 -0.0151 -0.0013 0.0803
-1.9992 1.0001 -1.9947 0.2107 -0.0440 -0.1375
-0.9996 0.0000 0.0004 0.0151 0.0013 -0.0803
0.9995 -0.9996 0.9962 -0.1567 -0.0127 0.0584
-0.9996 -0.9995 0.9970 -0.1265 -0.0101 -0.1022
-1.9990 0.9990 0.0032 0.1329 0.0722 -0.1400
-0.9998 -1.9979 -0.0044 -0.1903 -0.1376 -0.1214
0.9994 -0.9990 -0.0028 -0.1178 -0.0708 0.0597
0.9999 1.9974 1.0033 0.1514 0.1957 0.1201
-0.9993 0.9984 1.0017 0.0788 0.1289 -0.0610
-0.9994 -0.0011 1.9983 -0.0628 0.1175 -0.0829
-0.9997 0.0006 -0.9986 0.0540 -0.0568 -0.0790
-0.0001 0.0006 -0.9990 0.0389 -0.0581 0.0013
0.0001 -0.0006 0.9990 -0.0389 0.0581 -0.0013
-1.9995 -0.9978 -1.9995 0.0054 -0.1830 -0.1786

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            71168
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.618
_diffrn_reflns_theta_min         2.344
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  -6.00   0.50    0.35    --  -44.25 115.00-101.00  154
  2  ω   -117.00 -45.00   0.50    0.35    --  -44.25-170.00  26.00  144
  3  ω     57.00 123.00   0.50    0.35    --   44.25-170.00  26.00  132
  4  ω     27.00  88.00   0.50    0.35    --   44.25-115.00 169.00  122
  5  ω     66.00 118.00   0.50    0.35    --   44.25 170.00  41.00  104
  6  ω   -118.00 -35.00   0.50    1.40    --  -96.00 170.00  41.00  166
  7  ω   -134.00 -45.00   0.50    1.40    --  -96.00-170.00  26.00  178
  8  ω   -154.00 -89.00   0.50    1.40    --  -96.00-115.00 169.00  130
  9  ω    -79.00 -54.00   0.50    1.40    --  -96.00 115.00-101.00   50
 10  ω    109.00 134.00   0.50    1.40    --  117.50 170.00  41.00   50
 11  ω     70.00 143.00   0.50    1.40    --  117.50-170.00  26.00  146
 12  ω    133.00 159.00   0.50    1.40    --  117.50 115.00-101.00   52
 13  ω     65.00  90.00   0.50    1.40    --  117.50-115.00 169.00   50
 14  ω    -40.00  18.00   0.50    0.35    --  -44.25  38.00  30.00  116
 15  ω   -116.00 -24.00   0.50    0.35    --  -44.25 -57.00  90.00  184
 16  ω      1.00  27.00   0.50    0.35    --   44.25 -19.00   0.00   52
 17  ω    -34.00  -6.00   0.50    0.35    --   44.25 -19.00   0.00   56
 18  ω    -51.00 -21.00   0.50    1.40    --  -96.00  45.00  90.00   60
 19  ω     48.00 111.00   0.50    1.40    --  117.50-125.00-120.00  126
 20  ω     96.00 142.00   0.50    1.40    --  117.50 125.00  90.00   92
 21  ω     45.00  70.00   0.50    1.40    --  117.50 -61.00 -60.00   50
 22  ω    111.00 137.00   0.50    1.40    --  117.50  61.00-150.00   52
 23  ω     75.00 100.00   0.50    1.40    --  117.50 -77.00-150.00   50
 24  ω     52.00  77.00   0.50    1.40    --  117.50-125.00 120.00   50
 25  ω     65.00 104.00   0.50    1.40    --  117.50 -95.00-180.00   78
 26  ω     75.00 111.00   0.50    1.40    --  117.50-125.00 -90.00   72
 27  ω     68.00 107.00   0.50    1.40    --  117.50-125.00 -60.00   78
 28  ω     45.00  70.00   0.50    1.40    --  117.50 -61.00  60.00   50
 29  ω     91.00 174.00   0.50    1.40    --  117.50  77.00 -90.00  166
 30  ω     57.00 104.00   0.50    1.40    --  117.50 -95.00-150.00   94
 31  ω    140.00 165.00   0.50    1.40    --  117.50  61.00 150.00   50
 32  ω    107.00 154.00   0.50    1.40    --  117.50 125.00  30.00   94
 33  ω    112.00 140.00   0.50    1.40    --  117.50  77.00-150.00   56
 34  ω     80.00 117.00   0.50    1.40    --  117.50 -87.00 116.49   74
 35  ω    152.00 178.00   0.50    1.40    --  117.50  61.00-150.00   52
 36  ω    106.00 146.00   0.50    1.40    --  117.50 -83.00-109.83   80
 37  ω     81.00 109.00   0.50    1.40    --  117.50-125.00 120.00   56
 38  ω    112.00 138.00   0.50    1.40    --  117.50 125.00-120.00   52
 39  ω     71.00 105.00   0.50    1.40    --  117.50 -77.00 -60.00   68
 40  ω     56.00  96.00   0.50    1.40    --  117.50 -77.00   0.00   80
 41  ω     61.00  90.00   0.50    1.40    --  117.50 -86.00 154.94   58
 42  ω    103.00 129.00   0.50    1.40    --  117.50 -86.00 154.94   52
 43  ω     97.00 170.00   0.50    1.40    --  117.50  61.00   0.00  146
 44  ω    104.00 138.00   0.50    1.40    --  117.50  45.00  90.00   68
 45  ω     88.00 118.00   0.50    1.40    --  117.50  15.00 -30.00   60
 46  ω     46.00  76.00   0.50    1.40    --  117.50 -95.00-120.00   60
 47  ω     49.00  75.00   0.50    1.40    --  117.50 -77.00  90.00   52
 48  ω     46.00  83.00   0.50    1.40    --  117.50 -95.00  90.00   74
 49  ω     51.00 110.00   0.50    1.40    --  117.50-125.00-180.00  118
 50  ω     49.00 107.00   0.50    1.40    --  117.50-125.00-150.00  116
 51  ω    129.00 176.00   0.50    1.40    --  117.50  61.00-120.00   94
 52  ω     55.00  81.00   0.50    1.40    --  117.50 -95.00 150.00   52
 53  ω    125.00 167.00   0.50    1.40    --  117.50  77.00-180.00   84
 54  ω    107.00 133.00   0.50    1.40    --  117.50  61.00 150.00   52
 55  ω    144.00 178.00   0.50    1.40    --  117.50  77.00-150.00   68
 56  ω     98.00 134.00   0.50    1.40    --  117.50  45.00  60.00   72
 57  ω     45.00  70.00   0.50    1.40    --  117.50 -61.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0151032000
_diffrn_orient_matrix_UB_12      0.1028882000
_diffrn_orient_matrix_UB_13      -0.0389191000
_diffrn_orient_matrix_UB_21      -0.0013074000
_diffrn_orient_matrix_UB_22      0.0694225000
_diffrn_orient_matrix_UB_23      0.0582014000
_diffrn_orient_matrix_UB_31      0.0803376000
_diffrn_orient_matrix_UB_32      0.0205768000
_diffrn_orient_matrix_UB_33      -0.0012906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10520
_reflns_number_total             11049
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         11049
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.044
_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)+(0.0498P)²+3.6554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 Cl2B-C5A \\sim C5A-Cl2A
 with sigma of 0.02
 C8B-C7A \\sim C7A-C8A
 with sigma of 0.02
 C5E-C4E \\sim C5F-C4F
 with sigma of 0.02
 C7B-C8B \\sim C7A-C8A
 with sigma of 0.02
 O1H-C7G \\sim C7G-O1G
 with sigma of 0.02
 Cl1C-C9C \\sim C9C-Cl1D
 with sigma of 0.02
 O1B-C7B \\sim O1A-C7A
 with sigma of 0.02
 C4F-C3F \\sim C4E-C3E
 with sigma of 0.02
 O1F-C7E \\sim C7E-O1E
 with sigma of 0.02
 C3F-C2E \\sim C2E-C3E
 with sigma of 0.02
 C5F-C6E \\sim C6E-C5E
 with sigma of 0.02
 Cl1A-C1A \\sim C1A-Cl1B
 with sigma of 0.02
 C8B-C9B \\sim C8A-C9A
 with sigma of 0.02
 C9B-C10B \\sim C9A-C10A
 with sigma of 0.02
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 C11A-C12A \\sim C11B-C12B
 with sigma of 0.02
 C12B-C13B \\sim C12A-C13A
 with sigma of 0.02
 C13B-C8B \\sim C13A-C8A
 with sigma of 0.02
 Cl2C-C13C \\sim C13C-Cl2D
 with sigma of 0.02
 Cl2F-C13E \\sim C13E-Cl2E
 with sigma of 0.02
 Cl1F-C9E \\sim C9E-Cl1E
 with sigma of 0.02
 Cl2H-C13G \\sim C13G-Cl2G
 with sigma of 0.02
 Cl1H-C9G \\sim C9G-Cl1G
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1C) = Uanis(Cl1D)
Uanis(C7A) = Uanis(C7B)
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11B) = Uanis(C11A)
Uanis(C12B) = Uanis(C12A)
Uanis(C13A) = Uanis(C13B)
Uanis(Cl2D) = Uanis(Cl2C)
Uanis(C3F) = Uanis(C3E)
Uanis(C4F) = Uanis(C4E)
Uanis(C5F) = Uanis(C5E)
Uanis(O1E) = Uanis(O1F)
Uanis(Cl1H) = Uanis(Cl1G)
Uanis(Cl2H) = Uanis(Cl2G)
Uanis(Cl2B) = Uanis(Cl2A)
Uanis(Cl1A) = Uanis(Cl1B)
Uanis(O1A) = Uanis(O1B)
Uanis(O1H) = Uanis(O1G)
Uanis(Cl1E) = Uanis(Cl1F)
Uanis(Cl2F) = Uanis(Cl2E)
4. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(O1B)=Sof(H1B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=
 Sof(C9B)=Sof(H9C)=Sof(H9D)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C11B)=Sof(H11C)=
 Sof(H11D)=Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(O1A)=Sof(H1A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=
 Sof(C9A)=Sof(H9A)=Sof(H9B)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(H11A)=
 Sof(H11B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=FVAR(1)
 Sof(Cl1D)=Sof(Cl2D)=1-FVAR(2)
 Sof(Cl1C)=Sof(Cl2C)=FVAR(2)
 Sof(Cl1F)=Sof(Cl2F)=Sof(O1F)=Sof(H2)=Sof(H2K)=Sof(H2L)=Sof(C3F)=Sof(H3M)=
 Sof(H3N)=Sof(C4F)=Sof(H4M)=Sof(H4N)=Sof(C5F)=Sof(H5M)=Sof(H5N)=Sof(H6O)=
 Sof(H7X)=1-FVAR(3)
 Sof(Cl1E)=Sof(Cl2E)=Sof(O1E)=Sof(H1)=Sof(H2I)=Sof(H2J)=Sof(C3E)=Sof(H3I)=
 Sof(H3J)=Sof(C4E)=Sof(H4I)=Sof(H4J)=Sof(C5E)=Sof(H5I)=Sof(H5J)=Sof(H6E)=
 Sof(H7E)=FVAR(3)
 Sof(Cl1H)=Sof(Cl2H)=Sof(O1H)=Sof(H1H)=Sof(H7Y)=1-FVAR(4)
 Sof(Cl1G)=Sof(Cl2G)=Sof(O1G)=Sof(H1G)=Sof(H7G)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C6C(H6C), C6G(H6G), C7A(H7A), C7B(H7B), C7C(H7C), C7G(H7Y), C7G(H7G),
 C8A(H8A), C8B(H8B), C6E(H6E), C6E(H6O), C7E(H7X), C7E(H7E)
5.b Secondary CH2 refined with riding coordinates:
 C1C(H1E,H1F), C1G(H1R,H1S), C2C(H2E,H2F), C2G(H2R,H2S), C3C(H3E,H3F), C3G(H3R,
 H3S), C4C(H4E,H4F), C4G(H4R,H4S), C5C(H5E,H5F), C5G(H5R,H5S), C9A(H9A,H9B),
 C9B(H9C,H9D), C10A(H10A,H10B), C10B(H10C,H10D), C11A(H11A,H11B), C11B(H11C,
 H11D), C12A(H12A,H12B), C12B(H12C,H12D), C13A(H13A,H13B), C13B(H13C,H13D),
 C1E(H1I,H1J), C2E(H2I,H2J), C2E(H2K,H2L), C3E(H3I,H3J), C3F(H3M,H3N), C4E(H4I,
 H4J), C4F(H4M,H4N), C5E(H5I,H5J), C5F(H5M,H5N)
5.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C10C(H10F), C10G(H10G), C11C(H11F), C11G(H11G),
 C12C(H12F), C12G(H12G), C10E(H10E), C11E(H11E), C12E(H12E)
5.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B), O1C(H1C), O1G(H1G), O1H(H1H), O1E(H1), O1F(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.20421(11) 0.26400(15) 0.62448(9) 0.0313(3) Uani 0.5675(12) 1 d D . P
A 1
Cl1B Cl 0.21400(15) 0.2414(2) 0.61103(12) 0.0313(3) Uani 0.4325(12) 1 d D . P A
2
Cl1C Cl 0.45359(3) 0.40049(7) 0.83911(4) 0.03537(17) Uani 0.986(3) 1 d D . P B
1
Cl1D Cl 0.452(2) 0.430(4) 0.821(2) 0.03537(17) Uani 0.014(3) 1 d D . P B 2
Cl1G Cl 0.06784(16) 0.57729(15) 0.65044(8) 0.0256(3) Uani 0.750(11) 1 d D . P C
1
Cl1H Cl 0.0522(3) 0.5889(4) 0.6560(2) 0.0256(3) Uani 0.250(11) 1 d D . P C 2
Cl2A Cl 0.17020(13) 0.6525(2) 0.50127(10) 0.0269(3) Uani 0.5675(12) 1 d D . P A
1
Cl2B Cl 0.15810(19) 0.6447(3) 0.51313(15) 0.0269(3) Uani 0.4325(12) 1 d D . P A
2
Cl2C Cl 0.40420(3) 0.12416(8) 0.64596(2) 0.02833(17) Uani 0.986(3) 1 d D . P B
1
Cl2D Cl 0.3904(18) 0.165(5) 0.6438(13) 0.02833(17) Uani 0.014(3) 1 d D . P B 2
Cl2G Cl 0.0983(3) 0.8604(5) 0.8459(2) 0.0257(4) Uani 0.750(11) 1 d D . P C 1
Cl2H Cl 0.1021(9) 0.8652(16) 0.8407(7) 0.0257(4) Uani 0.250(11) 1 d D . P C 2
O1A O 0.24919(12) 0.4832(2) 0.66192(10) 0.0275(4) Uani 0.5675(12) 1 d D . P A 1
H1A H 0.290654 0.464448 0.673763 0.041 Uiso 0.5675(12) 1 calc R U P A 1
O1B O 0.21879(17) 0.4650(3) 0.66849(14) 0.0275(4) Uani 0.4325(12) 1 d D . P A 2
H1B H 0.218500 0.522109 0.689585 0.041 Uiso 0.4325(12) 1 calc R U P A 2
O1C O 0.32614(7) 0.37661(10) 0.74800(6) 0.0339(3) Uani 1 1 d . . . . .
H1C H 0.304500 0.388257 0.779346 0.051 Uiso 1 1 calc R U . . .
O1G O 0.1941(2) 0.6250(3) 0.7400(2) 0.0255(6) Uani 0.750(11) 1 d D . P C 1
H1G H 0.181439 0.592010 0.707663 0.038 Uiso 0.750(11) 1 calc R U P C 1
O1H O 0.1790(7) 0.6186(10) 0.7438(9) 0.0255(6) Uani 0.250(11) 1 d D . P C 2
H1H H 0.217316 0.612069 0.765273 0.038 Uiso 0.250(11) 1 calc R U P C 2
C1A C 0.16452(8) 0.34228(16) 0.56686(8) 0.0307(4) Uani 1 1 d D . . . .
C1C C 0.24918(8) 0.19963(14) 0.80559(8) 0.0290(3) Uani 1 1 d . . . . .
H1E H 0.228917 0.274160 0.802366 0.035 Uiso 1 1 calc R U . . .
H1F H 0.230181 0.157211 0.769841 0.035 Uiso 1 1 calc R U . . .
C1G C 0.25722(7) 0.80553(14) 0.68144(7) 0.0239(3) Uani 1 1 d . . . . .
H1R H 0.276403 0.845598 0.717985 0.029 Uiso 1 1 calc R U . . .
H1S H 0.279515 0.732323 0.681902 0.029 Uiso 1 1 calc R U . . .
C2A C 0.10877(9) 0.29683(18) 0.53077(9) 0.0406(4) Uani 1 1 d . . . . .
H2A H 0.096441 0.222264 0.535629 0.049 Uiso 1 1 calc R U . . .
C2C C 0.22687(9) 0.14540(15) 0.86352(9) 0.0334(4) Uani 1 1 d . . . . .
H2E H 0.174488 0.140492 0.862037 0.040 Uiso 1 1 calc R U . . .
H2F H 0.242953 0.190551 0.899115 0.040 Uiso 1 1 calc R U . . .
C2G C 0.27598(8) 0.86722(16) 0.62441(8) 0.0305(4) Uani 1 1 d . . . . .
H2R H 0.328060 0.876629 0.625127 0.037 Uiso 1 1 calc R U . . .
H2S H 0.260595 0.823928 0.587919 0.037 Uiso 1 1 calc R U . . .
C3A C 0.07135(9) 0.36056(17) 0.48779(8) 0.0361(4) Uani 1 1 d . . . . .
H3A H 0.033329 0.329915 0.462894 0.043 Uiso 1 1 calc R U . . .
C3C C 0.25872(9) 0.03108(15) 0.87063(9) 0.0328(4) Uani 1 1 d . . . . .
H3E H 0.238059 -0.016571 0.837693 0.039 Uiso 1 1 calc R U . . .
H3F H 0.246610 -0.000397 0.909924 0.039 Uiso 1 1 calc R U . . .
C3G C 0.24038(8) 0.97856(15) 0.62065(7) 0.0299(4) Uani 1 1 d . . . . .
H3R H 0.250745 1.014662 0.582102 0.036 Uiso 1 1 calc R U . . .
H3S H 0.259787 1.024885 0.654670 0.036 Uiso 1 1 calc R U . . .
C4A C 0.08949(8) 0.46869(16) 0.48124(7) 0.0290(3) Uani 1 1 d . . . . .
H4A H 0.063979 0.513263 0.451974 0.035 Uiso 1 1 calc R U . . .
C4C C 0.33959(8) 0.03431(15) 0.86827(8) 0.0310(4) Uani 1 1 d . . . . .
H4E H 0.360681 0.073687 0.904372 0.037 Uiso 1 1 calc R U . . .
H4F H 0.358354 -0.041233 0.869585 0.037 Uiso 1 1 calc R U . . .
C4G C 0.16008(8) 0.96756(15) 0.62361(8) 0.0289(3) Uani 1 1 d . . . . .
H4R H 0.138424 1.041200 0.623619 0.035 Uiso 1 1 calc R U . . .
H4S H 0.140057 0.928223 0.587110 0.035 Uiso 1 1 calc R U . . .
C5A C 0.14530(8) 0.51180(14) 0.51776(7) 0.0248(3) Uani 1 1 d D . . . .
C5C C 0.36137(8) 0.09092(13) 0.81069(8) 0.0247(3) Uani 1 1 d . . . . .
H5E H 0.344463 0.047556 0.774635 0.030 Uiso 1 1 calc R U . . .
H5F H 0.413756 0.095117 0.811636 0.030 Uiso 1 1 calc R U . . .
C5G C 0.14151(7) 0.90577(13) 0.68061(7) 0.0226(3) Uani 1 1 d . . . . .
H5R H 0.089390 0.897250 0.680327 0.027 Uiso 1 1 calc R U . . .
H5S H 0.157658 0.948399 0.717156 0.027 Uiso 1 1 calc R U . . .
C6A C 0.18487(7) 0.45120(14) 0.56237(6) 0.0226(3) Uani 1 1 d . . . . .
C6C C 0.33011(7) 0.20622(12) 0.80552(7) 0.0210(3) Uani 1 1 d . . . . .
H6C H 0.348303 0.248901 0.842025 0.025 Uiso 1 1 calc R U . . .
C6G C 0.17661(7) 0.79300(12) 0.68355(6) 0.0188(3) Uani 1 1 d . . . . .
H6G H 0.158371 0.750249 0.647091 0.023 Uiso 1 1 calc R U . . .
C7A C 0.2474(3) 0.5157(5) 0.5997(3) 0.0185(9) Uani 0.5675(12) 1 d D . P A 1
H7A H 0.234776 0.595082 0.598078 0.022 Uiso 0.5675(12) 1 calc R U P A 1
C7B C 0.2371(5) 0.4919(8) 0.6082(4) 0.0185(9) Uani 0.4325(12) 1 d D . P A 2
H7B H 0.235063 0.573410 0.605318 0.022 Uiso 0.4325(12) 1 calc R U P A 2
C7C C 0.35117(8) 0.26662(12) 0.74858(7) 0.0219(3) Uani 1 1 d . . . . .
H7C H 0.327229 0.228801 0.712532 0.026 Uiso 1 1 calc R U . . .
C7G C 0.15931(7) 0.72970(12) 0.74060(6) 0.0189(3) Uani 1 1 d D . . . .
H7Y H 0.182237 0.768041 0.776909 0.023 Uiso 0.250(11) 1 calc R U P C 2
H7G H 0.180931 0.770909 0.776430 0.023 Uiso 0.750(11) 1 calc R U P C 1
C8A C 0.32105(13) 0.5041(2) 0.57452(12) 0.0194(4) Uani 0.5675(12) 1 d D . P A 1
H8A H 0.316548 0.528079 0.531070 0.023 Uiso 0.5675(12) 1 calc R U P A 1
C8B C 0.31530(17) 0.4602(3) 0.60144(16) 0.0194(4) Uani 0.4325(12) 1 d D . P A 2
H8B H 0.324042 0.388595 0.622480 0.023 Uiso 0.4325(12) 1 calc R U P A 2
C8C C 0.43053(8) 0.26528(12) 0.74075(7) 0.0225(3) Uani 1 1 d . . . . .
C8G C 0.08010(8) 0.72049(12) 0.74868(6) 0.0201(3) Uani 1 1 d . . . . .
C9A C 0.34916(13) 0.3872(2) 0.57598(12) 0.0218(4) Uani 0.5675(12) 1 d D . P A 1
H9A H 0.316823 0.340540 0.549915 0.026 Uiso 0.5675(12) 1 calc R U P A 1
H9B H 0.349750 0.358849 0.618048 0.026 Uiso 0.5675(12) 1 calc R U P A 1
C9B C 0.33492(17) 0.4469(3) 0.53565(15) 0.0218(4) Uani 0.4325(12) 1 d D . P A 2
H9C H 0.326641 0.516449 0.513396 0.026 Uiso 0.4325(12) 1 calc R U P A 2
H9D H 0.304668 0.389977 0.515118 0.026 Uiso 0.4325(12) 1 calc R U P A 2
C9C C 0.48028(9) 0.32388(14) 0.77777(7) 0.0285(3) Uani 1 1 d D . . . .
C9G C 0.03397(9) 0.65429(14) 0.71193(7) 0.0262(3) Uani 1 1 d D . . . .
C10A C 0.42419(17) 0.3801(3) 0.55385(15) 0.0236(6) Uani 0.5675(12) 1 d D . P A
1
H10A H 0.441478 0.303934 0.557657 0.028 Uiso 0.5675(12) 1 calc R U P A 1
H10B H 0.422864 0.400916 0.510404 0.028 Uiso 0.5675(12) 1 calc R U P A 1
C10B C 0.4134(2) 0.4141(4) 0.5349(2) 0.0236(6) Uani 0.4325(12) 1 d D . P A 2
H10C H 0.420668 0.341871 0.554584 0.028 Uiso 0.4325(12) 1 calc R U P A 2
H10D H 0.426187 0.407515 0.492277 0.028 Uiso 0.4325(12) 1 calc R U P A 2
C10C C 0.55234(10) 0.32432(18) 0.76904(9) 0.0402(5) Uani 1 1 d . . . . .
H10F H 0.584073 0.366974 0.794618 0.048 Uiso 1 1 calc R U . . .
C10G C -0.03730(9) 0.64305(16) 0.72109(8) 0.0355(4) Uani 1 1 d . . . . .
H10G H -0.066438 0.596124 0.695722 0.043 Uiso 1 1 calc R U . . .
C11A C 0.47517(14) 0.4557(2) 0.59084(15) 0.0274(5) Uani 0.5675(12) 1 d D . P A
1
H11A H 0.479220 0.431761 0.633828 0.033 Uiso 0.5675(12) 1 calc R U P A 1
H11B H 0.522842 0.451436 0.575048 0.033 Uiso 0.5675(12) 1 calc R U P A 1
C11B C 0.46186(19) 0.4980(3) 0.5680(2) 0.0274(5) Uani 0.4325(12) 1 d D . P A 2
H11C H 0.511604 0.472439 0.568758 0.033 Uiso 0.4325(12) 1 calc R U P A 2
H11D H 0.458563 0.568175 0.545683 0.033 Uiso 0.4325(12) 1 calc R U P A 2
C11C C 0.57751(10) 0.2623(2) 0.72292(9) 0.0438(5) Uani 1 1 d . . . . .
H11F H 0.626805 0.261723 0.716945 0.053 Uiso 1 1 calc R U . . .
C11G C -0.06584(9) 0.70062(18) 0.76745(9) 0.0390(4) Uani 1 1 d . . . . .
H11G H -0.114819 0.693605 0.773840 0.047 Uiso 1 1 calc R U . . .
C12A C 0.44863(14) 0.5727(2) 0.58701(14) 0.0273(5) Uani 0.5675(12) 1 d D . P A
1
H12A H 0.448268 0.598325 0.544416 0.033 Uiso 0.5675(12) 1 calc R U P A 1
H12B H 0.481321 0.620162 0.612231 0.033 Uiso 0.5675(12) 1 calc R U P A 1
C12B C 0.44177(18) 0.5162(3) 0.63304(18) 0.0273(5) Uani 0.4325(12) 1 d D . P A
2
H12C H 0.471127 0.575867 0.651835 0.033 Uiso 0.4325(12) 1 calc R U P A 2
H12D H 0.451744 0.448986 0.657099 0.033 Uiso 0.4325(12) 1 calc R U P A 2
C12C C 0.53131(9) 0.20114(17) 0.68549(8) 0.0345(4) Uani 1 1 d . . . . .
H12F H 0.548290 0.157872 0.653848 0.041 Uiso 1 1 calc R U . . .
C12G C -0.02314(9) 0.76857(16) 0.80464(8) 0.0318(4) Uani 1 1 d . . . . .
H12G H -0.042552 0.808813 0.836347 0.038 Uiso 1 1 calc R U . . .
C13A C 0.37348(14) 0.5820(2) 0.60906(14) 0.0241(5) Uani 0.5675(12) 1 d D . P A
1
H13A H 0.356477 0.658118 0.603414 0.029 Uiso 0.5675(12) 1 calc R U P A 1
H13B H 0.375092 0.565091 0.653021 0.029 Uiso 0.5675(12) 1 calc R U P A 1
C13B C 0.36333(19) 0.5457(3) 0.63467(19) 0.0241(5) Uani 0.4325(12) 1 d D . P A
2
H13C H 0.354749 0.617958 0.615388 0.029 Uiso 0.4325(12) 1 calc R U P A 2
H13D H 0.351107 0.551065 0.677484 0.029 Uiso 0.4325(12) 1 calc R U P A 2
C13C C 0.45935(8) 0.20406(13) 0.69499(7) 0.0248(3) Uani 1 1 d D . . . .
C13G C 0.04837(8) 0.77691(13) 0.79486(7) 0.0227(3) Uani 1 1 d D . . . .
Cl1E Cl 0.27573(12) 0.75842(18) 0.88619(10) 0.0245(3) Uani 0.722(6) 1 d D . P D
1
Cl1F Cl 0.2844(3) 0.7480(5) 0.8780(3) 0.0245(3) Uani 0.278(6) 1 d D . P D 2
Cl2E Cl 0.35204(11) 0.35502(16) 0.97526(9) 0.0268(3) Uani 0.722(6) 1 d D . P D
1
Cl2F Cl 0.3426(3) 0.3546(5) 0.9860(2) 0.0268(3) Uani 0.278(6) 1 d D . P D 2
O1E O 0.2842(3) 0.5389(3) 0.82455(17) 0.0202(6) Uani 0.722(6) 1 d D . P D 1
H1 H 0.247095 0.552193 0.802579 0.030 Uiso 0.722(6) 1 calc R U P D 1
O1F O 0.2884(8) 0.5139(9) 0.8211(5) 0.0202(6) Uani 0.278(6) 1 d D . P D 2
H2 H 0.316146 0.462815 0.813674 0.030 Uiso 0.278(6) 1 calc R U P D 2
C1E C 0.14237(8) 0.44257(14) 0.84970(8) 0.0299(3) Uani 1 1 d . . . . .
H1I H 0.155886 0.446000 0.807191 0.036 Uiso 1 1 calc R U . . .
H1J H 0.152912 0.368029 0.865246 0.036 Uiso 1 1 calc R U . . .
C2E C 0.06287(8) 0.46457(17) 0.85098(8) 0.0342(4) Uani 1 1 d D . . . .
H2I H 0.036191 0.403054 0.831220 0.041 Uiso 0.722(6) 1 calc R U P D 1
H2J H 0.050701 0.531616 0.827392 0.041 Uiso 0.722(6) 1 calc R U P D 1
H2K H 0.035740 0.421062 0.819434 0.041 Uiso 0.278(6) 1 calc R U P D 2
H2L H 0.052427 0.542960 0.843829 0.041 Uiso 0.278(6) 1 calc R U P D 2
C3E C 0.0402(2) 0.4785(4) 0.91586(17) 0.0489(12) Uani 0.722(6) 1 d D . P D 1
H3I H 0.045123 0.407654 0.937366 0.059 Uiso 0.722(6) 1 calc R U P D 1
H3J H -0.010485 0.499690 0.914107 0.059 Uiso 0.722(6) 1 calc R U P D 1
C3F C 0.0436(6) 0.4302(11) 0.9151(5) 0.0489(12) Uani 0.278(6) 1 d D . P D 2
H3M H -0.007933 0.438620 0.919200 0.059 Uiso 0.278(6) 1 calc R U P D 2
H3N H 0.056984 0.353135 0.923274 0.059 Uiso 0.278(6) 1 calc R U P D 2
C4E C 0.08464(15) 0.5659(4) 0.95236(14) 0.0464(11) Uani 0.722(6) 1 d D . P D 1
H4I H 0.076157 0.638625 0.933557 0.056 Uiso 0.722(6) 1 calc R U P D 1
H4J H 0.070007 0.568987 0.994550 0.056 Uiso 0.722(6) 1 calc R U P D 1
C4F C 0.0858(4) 0.5064(11) 0.9584(4) 0.0464(11) Uani 0.278(6) 1 d D . P D 2
H4M H 0.073429 0.492020 1.000518 0.056 Uiso 0.278(6) 1 calc R U P D 2
H4N H 0.073078 0.583074 0.948324 0.056 Uiso 0.278(6) 1 calc R U P D 2
C5E C 0.16403(16) 0.5373(4) 0.95299(14) 0.0336(8) Uani 0.722(6) 1 d D . P D 1
H5I H 0.192391 0.595526 0.974300 0.040 Uiso 0.722(6) 1 calc R U P D 1
H5J H 0.173169 0.468030 0.975355 0.040 Uiso 0.722(6) 1 calc R U P D 1
C5F C 0.1670(5) 0.4903(9) 0.9543(4) 0.0336(8) Uani 0.278(6) 1 d D . P D 2
H5M H 0.179837 0.412789 0.961715 0.040 Uiso 0.278(6) 1 calc R U P D 2
H5N H 0.193604 0.535588 0.985300 0.040 Uiso 0.278(6) 1 calc R U P D 2
C6E C 0.18658(8) 0.52550(15) 0.88824(7) 0.0251(3) Uani 1 1 d D . . . .
H6E H 0.177539 0.598081 0.868365 0.030 Uiso 0.722(6) 1 calc R U P D 1
H6O H 0.173596 0.602959 0.878252 0.030 Uiso 0.278(6) 1 calc R U P D 2
C7E C 0.26562(7) 0.50173(13) 0.88348(6) 0.0211(3) Uani 1 1 d D . . . .
H7X H 0.270564 0.421850 0.892292 0.025 Uiso 0.278(6) 1 calc R U P D 2
H7E H 0.273021 0.420910 0.885874 0.025 Uiso 0.722(6) 1 calc R U P D 1
C8E C 0.31720(7) 0.55628(12) 0.93031(6) 0.0180(3) Uani 1 1 d . . . . .
C9E C 0.32925(7) 0.66899(13) 0.93167(7) 0.0214(3) Uani 1 1 d D . . . .
C10E C 0.38068(9) 0.71849(14) 0.97055(8) 0.0284(3) Uani 1 1 d . . . . .
H10E H 0.386962 0.795469 0.969842 0.034 Uiso 1 1 calc R U . . .
C11E C 0.42269(8) 0.65446(15) 1.01033(7) 0.0285(3) Uani 1 1 d . . . . .
H11E H 0.458745 0.687214 1.036509 0.034 Uiso 1 1 calc R U . . .
C12E C 0.41210(8) 0.54276(14) 1.01192(7) 0.0243(3) Uani 1 1 d . . . . .
H12E H 0.440157 0.498513 1.039644 0.029 Uiso 1 1 calc R U . . .
C13E C 0.36003(7) 0.49589(13) 0.97257(7) 0.0207(3) Uani 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
Cl1A C1A 1.721(3) . ?
Cl1B C1A 1.795(3) . ?
Cl1C C9C 1.7495(18) . ?
Cl1D C9C 1.717(18) . ?
Cl1G C9G 1.806(4) . ?
Cl1H C9G 1.530(5) . ?
Cl2A C5A 1.829(3) . ?
Cl2B C5A 1.649(4) . ?
Cl2C C13C 1.7471(16) . ?
Cl2D C13C 1.732(17) . ?
Cl2G C13G 1.747(4) . ?
Cl2H C13G 1.753(13) . ?
O1A H1A 0.8400 . ?
O1A C7A 1.427(6) . ?
O1B H1B 0.8400 . ?
O1B C7B 1.436(8) . ?
O1C H1C 0.8400 . ?
O1C C7C 1.4267(18) . ?
O1G H1G 0.8400 . ?
O1G C7G 1.440(4) . ?
O1H H1H 0.8400 . ?
O1H C7G 1.411(12) . ?
C1A C2A 1.391(3) . ?
C1A C6A 1.393(3) . ?
C1C H1E 0.9900 . ?
C1C H1F 0.9900 . ?
C1C C2C 1.526(3) . ?
C1C C6C 1.532(2) . ?
C1G H1R 0.9900 . ?
C1G H1S 0.9900 . ?
C1G C2G 1.530(2) . ?
C1G C6G 1.5349(19) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.383(3) . ?
C2C H2E 0.9900 . ?
C2C H2F 0.9900 . ?
C2C C3C 1.527(2) . ?
C2G H2R 0.9900 . ?
C2G H2S 0.9900 . ?
C2G C3G 1.520(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.377(3) . ?
C3C H3E 0.9900 . ?
C3C H3F 0.9900 . ?
C3C C4C 1.533(2) . ?
C3G H3R 0.9900 . ?
C3G H3S 0.9900 . ?
C3G C4G 1.529(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.385(2) . ?
C4C H4E 0.9900 . ?
C4C H4F 0.9900 . ?
C4C C5C 1.529(2) . ?
C4G H4R 0.9900 . ?
C4G H4S 0.9900 . ?
C4G C5G 1.529(2) . ?
C5A C6A 1.405(2) . ?
C5C H5E 0.9900 . ?
C5C H5F 0.9900 . ?
C5C C6C 1.531(2) . ?
C5G H5R 0.9900 . ?
C5G H5S 0.9900 . ?
C5G C6G 1.531(2) . ?
C6A C7A 1.600(7) . ?
C6A C7B 1.450(11) . ?
C6C H6C 1.0000 . ?
C6C C7C 1.534(2) . ?
C6G H6G 1.0000 . ?
C6G C7G 1.5327(19) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.542(6) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.545(9) . ?
C7C H7C 1.0000 . ?
C7C C8C 1.522(2) . ?
C7G H7Y 1.0000 . ?
C7G H7G 1.0000 . ?
C7G C8G 1.5241(19) . ?
C8A H8A 1.0000 . ?
C8A C9A 1.526(4) . ?
C8A C13A 1.538(4) . ?
C8B H8B 1.0000 . ?
C8B C9B 1.532(5) . ?
C8B C13B 1.537(5) . ?
C8C C9C 1.399(2) . ?
C8C C13C 1.398(2) . ?
C8G C9G 1.405(2) . ?
C8G C13G 1.400(2) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C9A C10A 1.534(4) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C9B C10B 1.538(5) . ?
C9C C10C 1.389(3) . ?
C9G C10G 1.383(2) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.529(4) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.527(6) . ?
C10C H10F 0.9500 . ?
C10C C11C 1.381(3) . ?
C10G H10G 0.9500 . ?
C10G C11G 1.382(3) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.518(4) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C11B C12B 1.525(6) . ?
C11C H11F 0.9500 . ?
C11C C12C 1.379(3) . ?
C11G H11G 0.9500 . ?
C11G C12G 1.386(3) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C12A C13A 1.538(4) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C12B C13B 1.528(5) . ?
C12C H12F 0.9500 . ?
C12C C13C 1.391(2) . ?
C12G H12G 0.9500 . ?
C12G C13G 1.387(2) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
Cl1E C9E 1.756(2) . ?
Cl1F C9E 1.708(6) . ?
Cl2E C13E 1.732(3) . ?
Cl2F C13E 1.790(6) . ?
O1E H1 0.8400 . ?
O1E C7E 1.444(4) . ?
O1F H2 0.8400 . ?
O1F C7E 1.478(11) . ?
C1E H1I 0.9900 . ?
C1E H1J 0.9900 . ?
C1E C2E 1.528(2) . ?
C1E C6E 1.533(2) . ?
C2E H2I 0.9900 . ?
C2E H2J 0.9900 . ?
C2E H2K 0.9900 . ?
C2E H2L 0.9900 . ?
C2E C3E 1.532(4) . ?
C2E C3F 1.543(10) . ?
C3E H3I 0.9900 . ?
C3E H3J 0.9900 . ?
C3E C4E 1.550(5) . ?
C3F H3M 0.9900 . ?
C3F H3N 0.9900 . ?
C3F C4F 1.521(13) . ?
C4E H4I 0.9900 . ?
C4E H4J 0.9900 . ?
C4E C5E 1.540(4) . ?
C4F H4M 0.9900 . ?
C4F H4N 0.9900 . ?
C4F C5F 1.556(10) . ?
C5E H5I 0.9900 . ?
C5E H5J 0.9900 . ?
C5E C6E 1.526(3) . ?
C5F H5M 0.9900 . ?
C5F H5N 0.9900 . ?
C5F C6E 1.587(8) . ?
C6E H6E 1.0000 . ?
C6E H6O 1.0000 . ?
C6E C7E 1.5326(19) . ?
C7E H7X 1.0000 . ?
C7E H7E 1.0000 . ?
C7E C8E 1.5231(19) . ?
C8E C9E 1.398(2) . ?
C8E C13E 1.401(2) . ?
C9E C10E 1.389(2) . ?
C10E H10E 0.9500 . ?
C10E C11E 1.384(2) . ?
C11E H11E 0.9500 . ?
C11E C12E 1.383(2) . ?
C12E H12E 0.9500 . ?
C12E C13E 1.389(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A O1A H1A 109.5 . . ?
C7B O1B H1B 109.5 . . ?
C7C O1C H1C 109.5 . . ?
C7G O1G H1G 109.5 . . ?
C7G O1H H1H 109.5 . . ?
C2A C1A Cl1A 118.22(16) . . ?
C2A C1A Cl1B 112.32(18) . . ?
C2A C1A C6A 122.96(16) . . ?
C6A C1A Cl1A 118.51(15) . . ?
C6A C1A Cl1B 124.16(16) . . ?
H1E C1C H1F 108.0 . . ?
C2C C1C H1E 109.4 . . ?
C2C C1C H1F 109.4 . . ?
C2C C1C C6C 111.03(13) . . ?
C6C C1C H1E 109.4 . . ?
C6C C1C H1F 109.4 . . ?
H1R C1G H1S 108.0 . . ?
C2G C1G H1R 109.4 . . ?
C2G C1G H1S 109.4 . . ?
C2G C1G C6G 111.25(12) . . ?
C6G C1G H1R 109.4 . . ?
C6G C1G H1S 109.4 . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A C1A 119.77(19) . . ?
C3A C2A H2A 120.1 . . ?
C1C C2C H2E 109.5 . . ?
C1C C2C H2F 109.5 . . ?
C1C C2C C3C 110.76(14) . . ?
H2E C2C H2F 108.1 . . ?
C3C C2C H2E 109.5 . . ?
C3C C2C H2F 109.5 . . ?
C1G C2G H2R 109.4 . . ?
C1G C2G H2S 109.4 . . ?
H2R C2G H2S 108.0 . . ?
C3G C2G C1G 111.11(13) . . ?
C3G C2G H2R 109.4 . . ?
C3G C2G H2S 109.4 . . ?
C2A C3A H3A 120.2 . . ?
C4A C3A C2A 119.67(17) . . ?
C4A C3A H3A 120.2 . . ?
C2C C3C H3E 109.4 . . ?
C2C C3C H3F 109.4 . . ?
C2C C3C C4C 111.06(14) . . ?
H3E C3C H3F 108.0 . . ?
C4C C3C H3E 109.4 . . ?
C4C C3C H3F 109.4 . . ?
C2G C3G H3R 109.5 . . ?
C2G C3G H3S 109.5 . . ?
C2G C3G C4G 110.82(14) . . ?
H3R C3G H3S 108.1 . . ?
C4G C3G H3R 109.5 . . ?
C4G C3G H3S 109.5 . . ?
C3A C4A H4A 120.3 . . ?
C3A C4A C5A 119.33(16) . . ?
C5A C4A H4A 120.3 . . ?
C3C C4C H4E 109.3 . . ?
C3C C4C H4F 109.3 . . ?
H4E C4C H4F 108.0 . . ?
C5C C4C C3C 111.56(14) . . ?
C5C C4C H4E 109.3 . . ?
C5C C4C H4F 109.3 . . ?
C3G C4G H4R 109.3 . . ?
C3G C4G H4S 109.3 . . ?
H4R C4G H4S 108.0 . . ?
C5G C4G C3G 111.41(12) . . ?
C5G C4G H4R 109.3 . . ?
C5G C4G H4S 109.3 . . ?
C4A C5A Cl2A 116.04(15) . . ?
C4A C5A Cl2B 116.66(19) . . ?
C4A C5A C6A 123.49(16) . . ?
C6A C5A Cl2A 120.33(15) . . ?
C6A C5A Cl2B 119.43(19) . . ?
C4C C5C H5E 109.5 . . ?
C4C C5C H5F 109.5 . . ?
C4C C5C C6C 110.76(13) . . ?
H5E C5C H5F 108.1 . . ?
C6C C5C H5E 109.5 . . ?
C6C C5C H5F 109.5 . . ?
C4G C5G H5R 109.5 . . ?
C4G C5G H5S 109.5 . . ?
C4G C5G C6G 110.90(13) . . ?
H5R C5G H5S 108.0 . . ?
C6G C5G H5R 109.5 . . ?
C6G C5G H5S 109.5 . . ?
C1A C6A C5A 114.78(14) . . ?
C1A C6A C7A 129.3(2) . . ?
C1A C6A C7B 117.2(3) . . ?
C5A C6A C7A 115.9(2) . . ?
C5A C6A C7B 127.5(4) . . ?
C1C C6C H6C 108.2 . . ?
C1C C6C C7C 110.07(12) . . ?
C5C C6C C1C 109.36(12) . . ?
C5C C6C H6C 108.2 . . ?
C5C C6C C7C 112.59(12) . . ?
C7C C6C H6C 108.2 . . ?
C1G C6G H6G 108.3 . . ?
C5G C6G C1G 109.67(12) . . ?
C5G C6G H6G 108.3 . . ?
C5G C6G C7G 111.94(12) . . ?
C7G C6G C1G 110.20(11) . . ?
C7G C6G H6G 108.3 . . ?
O1A C7A C6A 108.9(3) . . ?
O1A C7A H7A 107.2 . . ?
O1A C7A C8A 111.1(5) . . ?
C6A C7A H7A 107.2 . . ?
C8A C7A C6A 114.9(5) . . ?
C8A C7A H7A 107.2 . . ?
O1B C7B C6A 111.7(5) . . ?
O1B C7B H7B 106.1 . . ?
O1B C7B C8B 109.1(6) . . ?
C6A C7B H7B 106.1 . . ?
C6A C7B C8B 117.0(7) . . ?
C8B C7B H7B 106.1 . . ?
O1C C7C C6C 110.92(13) . . ?
O1C C7C H7C 107.4 . . ?
O1C C7C C8C 109.75(13) . . ?
C6C C7C H7C 107.4 . . ?
C8C C7C C6C 113.74(12) . . ?
C8C C7C H7C 107.4 . . ?
O1G C7G C6G 108.6(2) . . ?
O1G C7G H7G 107.1 . . ?
O1G C7G C8G 112.80(19) . . ?
O1H C7G C6G 117.2(7) . . ?
O1H C7G H7Y 108.3 . . ?
O1H C7G C8G 100.4(5) . . ?
C6G C7G H7Y 108.3 . . ?
C6G C7G H7G 107.1 . . ?
C8G C7G C6G 113.69(11) . . ?
C8G C7G H7Y 108.3 . . ?
C8G C7G H7G 107.1 . . ?
C7A C8A H8A 107.5 . . ?
C9A C8A C7A 113.6(3) . . ?
C9A C8A H8A 107.5 . . ?
C9A C8A C13A 111.1(2) . . ?
C13A C8A C7A 109.3(3) . . ?
C13A C8A H8A 107.5 . . ?
C7B C8B H8B 107.6 . . ?
C9B C8B C7B 114.6(4) . . ?
C9B C8B H8B 107.6 . . ?
C9B C8B C13B 110.5(3) . . ?
C13B C8B C7B 108.6(5) . . ?
C13B C8B H8B 107.6 . . ?
C9C C8C C7C 123.74(15) . . ?
C13C C8C C7C 121.68(13) . . ?
C13C C8C C9C 114.59(14) . . ?
C9G C8G C7G 123.34(14) . . ?
C13G C8G C7G 121.55(13) . . ?
C13G C8G C9G 115.10(14) . . ?
C8A C9A H9A 109.2 . . ?
C8A C9A H9B 109.2 . . ?
C8A C9A C10A 112.0(2) . . ?
H9A C9A H9B 107.9 . . ?
C10A C9A H9A 109.2 . . ?
C10A C9A H9B 109.2 . . ?
C8B C9B H9C 109.7 . . ?
C8B C9B H9D 109.7 . . ?
C8B C9B C10B 109.7(3) . . ?
H9C C9B H9D 108.2 . . ?
C10B C9B H9C 109.7 . . ?
C10B C9B H9D 109.7 . . ?
C8C C9C Cl1C 120.50(13) . . ?
C8C C9C Cl1D 119.5(13) . . ?
C10C C9C Cl1C 116.39(13) . . ?
C10C C9C Cl1D 114.8(13) . . ?
C10C C9C C8C 123.11(17) . . ?
C8G C9G Cl1G 119.74(14) . . ?
C8G C9G Cl1H 127.0(2) . . ?
C10G C9G Cl1G 117.30(15) . . ?
C10G C9G Cl1H 110.1(2) . . ?
C10G C9G C8G 122.95(16) . . ?
C9A C10A H10A 109.4 . . ?
C9A C10A H10B 109.4 . . ?
H10A C10A H10B 108.0 . . ?
C11A C10A C9A 111.0(3) . . ?
C11A C10A H10A 109.4 . . ?
C11A C10A H10B 109.4 . . ?
C9B C10B H10C 109.3 . . ?
C9B C10B H10D 109.3 . . ?
H10C C10B H10D 108.0 . . ?
C11B C10B C9B 111.4(3) . . ?
C11B C10B H10C 109.3 . . ?
C11B C10B H10D 109.3 . . ?
C9C C10C H10F 120.2 . . ?
C11C C10C C9C 119.50(16) . . ?
C11C C10C H10F 120.2 . . ?
C9G C10G H10G 120.2 . . ?
C11G C10G C9G 119.50(16) . . ?
C11G C10G H10G 120.2 . . ?
C10A C11A H11A 109.6 . . ?
C10A C11A H11B 109.6 . . ?
H11A C11A H11B 108.1 . . ?
C12A C11A C10A 110.3(2) . . ?
C12A C11A H11A 109.6 . . ?
C12A C11A H11B 109.6 . . ?
C10B C11B H11C 109.3 . . ?
C10B C11B H11D 109.3 . . ?
H11C C11B H11D 108.0 . . ?
C12B C11B C10B 111.6(3) . . ?
C12B C11B H11C 109.3 . . ?
C12B C11B H11D 109.3 . . ?
C10C C11C H11F 119.9 . . ?
C12C C11C C10C 120.19(17) . . ?
C12C C11C H11F 119.9 . . ?
C10G C11G H11G 119.9 . . ?
C10G C11G C12G 120.15(16) . . ?
C12G C11G H11G 119.9 . . ?
C11A C12A H12A 109.4 . . ?
C11A C12A H12B 109.4 . . ?
C11A C12A C13A 111.2(2) . . ?
H12A C12A H12B 108.0 . . ?
C13A C12A H12A 109.4 . . ?
C13A C12A H12B 109.4 . . ?
C11B C12B H12C 109.4 . . ?
C11B C12B H12D 109.4 . . ?
C11B C12B C13B 111.3(3) . . ?
H12C C12B H12D 108.0 . . ?
C13B C12B H12C 109.4 . . ?
C13B C12B H12D 109.4 . . ?
C11C C12C H12F 120.6 . . ?
C11C C12C C13C 118.70(17) . . ?
C13C C12C H12F 120.6 . . ?
C11G C12G H12G 120.5 . . ?
C11G C12G C13G 118.98(17) . . ?
C13G C12G H12G 120.5 . . ?
C8A C13A H13A 109.2 . . ?
C8A C13A H13B 109.2 . . ?
C12A C13A C8A 112.0(2) . . ?
C12A C13A H13A 109.2 . . ?
C12A C13A H13B 109.2 . . ?
H13A C13A H13B 107.9 . . ?
C8B C13B H13C 109.3 . . ?
C8B C13B H13D 109.3 . . ?
C12B C13B C8B 111.7(3) . . ?
C12B C13B H13C 109.3 . . ?
C12B C13B H13D 109.3 . . ?
H13C C13B H13D 108.0 . . ?
C8C C13C Cl2C 120.07(12) . . ?
C8C C13C Cl2D 107.8(17) . . ?
C12C C13C Cl2C 116.04(13) . . ?
C12C C13C Cl2D 126.4(14) . . ?
C12C C13C C8C 123.89(15) . . ?
C8G C13G Cl2G 121.2(2) . . ?
C8G C13G Cl2H 117.6(6) . . ?
C12G C13G Cl2G 115.5(2) . . ?
C12G C13G Cl2H 119.1(6) . . ?
C12G C13G C8G 123.29(15) . . ?
C7E O1E H1 109.5 . . ?
C7E O1F H2 109.5 . . ?
H1I C1E H1J 107.9 . . ?
C2E C1E H1I 109.3 . . ?
C2E C1E H1J 109.3 . . ?
C2E C1E C6E 111.77(15) . . ?
C6E C1E H1I 109.3 . . ?
C6E C1E H1J 109.3 . . ?
C1E C2E H2I 109.2 . . ?
C1E C2E H2J 109.2 . . ?
C1E C2E H2K 110.7 . . ?
C1E C2E H2L 110.7 . . ?
C1E C2E C3E 112.2(2) . . ?
C1E C2E C3F 105.4(5) . . ?
H2I C2E H2J 107.9 . . ?
H2K C2E H2L 108.8 . . ?
C3E C2E H2I 109.2 . . ?
C3E C2E H2J 109.2 . . ?
C3F C2E H2K 110.7 . . ?
C3F C2E H2L 110.7 . . ?
C2E C3E H3I 109.1 . . ?
C2E C3E H3J 109.1 . . ?
C2E C3E C4E 112.6(3) . . ?
H3I C3E H3J 107.8 . . ?
C4E C3E H3I 109.1 . . ?
C4E C3E H3J 109.1 . . ?
C2E C3F H3M 110.7 . . ?
C2E C3F H3N 110.7 . . ?
H3M C3F H3N 108.8 . . ?
C4F C3F C2E 105.1(7) . . ?
C4F C3F H3M 110.7 . . ?
C4F C3F H3N 110.7 . . ?
C3E C4E H4I 109.7 . . ?
C3E C4E H4J 109.7 . . ?
H4I C4E H4J 108.2 . . ?
C5E C4E C3E 109.8(3) . . ?
C5E C4E H4I 109.7 . . ?
C5E C4E H4J 109.7 . . ?
C3F C4F H4M 109.4 . . ?
C3F C4F H4N 109.4 . . ?
C3F C4F C5F 111.2(9) . . ?
H4M C4F H4N 108.0 . . ?
C5F C4F H4M 109.4 . . ?
C5F C4F H4N 109.4 . . ?
C4E C5E H5I 109.6 . . ?
C4E C5E H5J 109.6 . . ?
H5I C5E H5J 108.1 . . ?
C6E C5E C4E 110.5(2) . . ?
C6E C5E H5I 109.6 . . ?
C6E C5E H5J 109.6 . . ?
C4F C5F H5M 110.0 . . ?
C4F C5F H5N 110.0 . . ?
C4F C5F C6E 108.3(6) . . ?
H5M C5F H5N 108.4 . . ?
C6E C5F H5M 110.0 . . ?
C6E C5F H5N 110.0 . . ?
C1E C6E C5F 100.1(4) . . ?
C1E C6E H6E 106.0 . . ?
C1E C6E H6O 113.0 . . ?
C5E C6E C1E 113.84(19) . . ?
C5E C6E H6E 106.0 . . ?
C5E C6E C7E 114.85(16) . . ?
C5F C6E H6O 113.0 . . ?
C7E C6E C1E 109.37(13) . . ?
C7E C6E C5F 107.6(3) . . ?
C7E C6E H6E 106.0 . . ?
C7E C6E H6O 113.0 . . ?
O1E C7E C6E 107.6(2) . . ?
O1E C7E H7E 108.5 . . ?
O1E C7E C8E 106.7(2) . . ?
O1F C7E C6E 113.2(6) . . ?
O1F C7E H7X 104.5 . . ?
O1F C7E C8E 111.9(6) . . ?
C6E C7E H7X 104.5 . . ?
C6E C7E H7E 108.5 . . ?
C8E C7E C6E 116.76(12) . . ?
C8E C7E H7X 104.5 . . ?
C8E C7E H7E 108.5 . . ?
C9E C8E C7E 122.86(13) . . ?
C9E C8E C13E 114.88(13) . . ?
C13E C8E C7E 122.11(13) . . ?
C8E C9E Cl1E 121.09(14) . . ?
C8E C9E Cl1F 118.2(3) . . ?
C10E C9E Cl1E 115.48(15) . . ?
C10E C9E Cl1F 118.2(3) . . ?
C10E C9E C8E 123.34(14) . . ?
C9E C10E H10E 120.4 . . ?
C11E C10E C9E 119.29(16) . . ?
C11E C10E H10E 120.4 . . ?
C10E C11E H11E 120.1 . . ?
C12E C11E C10E 119.90(15) . . ?
C12E C11E H11E 120.1 . . ?
C11E C12E H12E 120.3 . . ?
C11E C12E C13E 119.34(14) . . ?
C13E C12E H12E 120.3 . . ?
C8E C13E Cl2E 120.02(13) . . ?
C8E C13E Cl2F 121.0(2) . . ?
C12E C13E Cl2E 116.70(13) . . ?
C12E C13E Cl2F 115.3(2) . . ?
C12E C13E C8E 123.22(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1A O1C 0.84 2.03 2.651(3) 129.9 . yes
O1B H1B O1H 0.84 1.87 2.652(16) 153.8 . yes
O1C H1C O1E 0.84 2.14 2.760(3) 130.0 . yes
O1C H1C O1F 0.84 1.83 2.469(10) 131.7 . yes
O1G H1G Cl1G 0.84 2.42 3.044(5) 131.9 . yes
O1G H1G O1A 0.84 2.15 2.706(5) 123.7 . yes
O1H H1H O1F 0.84 2.13 2.88(2) 149.6 . yes
O1E H1 O1G 0.84 1.87 2.653(6) 154.0 . yes
O1F H2 Cl1D 0.84 2.60 3.26(4) 137.2 . yes
O1F H2 O1C 0.84 1.81 2.469(10) 133.7 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1A C1A C2A C3A 174.00(16) . . . . ?
Cl1A C1A C6A C5A -174.30(12) . . . . ?
Cl1A C1A C6A C7A 7.0(4) . . . . ?
Cl1B C1A C2A C3A -171.13(17) . . . . ?
Cl1B C1A C6A C5A 169.82(14) . . . . ?
Cl1B C1A C6A C7B -17.7(5) . . . . ?
Cl1C C9C C10C C11C 177.54(17) . . . . ?
Cl1D C9C C10C C11C -163(2) . . . . ?
Cl1G C9G C10G C11G -179.76(16) . . . . ?
Cl1H C9G C10G C11G -176.5(2) . . . . ?
Cl2A C5A C6A C1A -174.49(13) . . . . ?
Cl2A C5A C6A C7A 4.4(3) . . . . ?
Cl2B C5A C6A C1A 173.15(16) . . . . ?
Cl2B C5A C6A C7B 1.6(5) . . . . ?
O1A C7A C8A C9A 61.2(5) . . . . ?
O1A C7A C8A C13A -63.5(5) . . . . ?
O1B C7B C8B C9B 159.9(5) . . . . ?
O1B C7B C8B C13B -76.0(6) . . . . ?
O1C C7C C8C C9C 54.21(19) . . . . ?
O1C C7C C8C C13C -125.73(15) . . . . ?
O1G C7G C8G C9G -52.7(3) . . . . ?
O1G C7G C8G C13G 126.0(3) . . . . ?
O1H C7G C8G C9G -54.6(8) . . . . ?
O1H C7G C8G C13G 124.1(8) . . . . ?
C1A C2A C3A C4A -0.2(3) . . . . ?
C1A C6A C7A O1A -41.0(6) . . . . ?
C1A C6A C7A C8A 84.4(4) . . . . ?
C1A C6A C7B O1B -49.2(8) . . . . ?
C1A C6A C7B C8B 77.5(5) . . . . ?
C1C C2C C3C C4C 54.9(2) . . . . ?
C1C C6C C7C O1C 62.64(16) . . . . ?
C1C C6C C7C C8C -173.08(13) . . . . ?
C1G C2G C3G C4G -55.41(18) . . . . ?
C1G C6G C7G O1G -57.7(2) . . . . ?
C1G C6G C7G O1H -67.5(7) . . . . ?
C1G C6G C7G C8G 175.88(12) . . . . ?
C2A C1A C6A C5A -0.9(2) . . . . ?
C2A C1A C6A C7A -179.6(3) . . . . ?
C2A C1A C6A C7B 171.6(4) . . . . ?
C2A C3A C4A C5A 0.3(3) . . . . ?
C2C C1C C6C C5C 58.95(17) . . . . ?
C2C C1C C6C C7C -176.88(13) . . . . ?
C2C C3C C4C C5C -54.4(2) . . . . ?
C2G C1G C6G C5G -57.09(16) . . . . ?
C2G C1G C6G C7G 179.25(13) . . . . ?
C2G C3G C4G C5G 55.59(19) . . . . ?
C3A C4A C5A Cl2A 174.94(15) . . . . ?
C3A C4A C5A Cl2B -173.08(17) . . . . ?
C3A C4A C5A C6A -0.7(2) . . . . ?
C3C C4C C5C C6C 56.17(19) . . . . ?
C3G C4G C5G C6G -56.72(18) . . . . ?
C4A C5A C6A C1A 1.0(2) . . . . ?
C4A C5A C6A C7A 179.9(3) . . . . ?
C4A C5A C6A C7B -170.6(4) . . . . ?
C4C C5C C6C C1C -57.82(17) . . . . ?
C4C C5C C6C C7C 179.49(12) . . . . ?
C4G C5G C6G C1G 56.89(16) . . . . ?
C4G C5G C6G C7G 179.53(12) . . . . ?
C5A C6A C7A O1A 140.3(3) . . . . ?
C5A C6A C7A C8A -94.3(4) . . . . ?
C5A C6A C7B O1B 122.3(5) . . . . ?
C5A C6A C7B C8B -111.0(6) . . . . ?
C5C C6C C7C O1C -175.08(12) . . . . ?
C5C C6C C7C C8C -50.80(16) . . . . ?
C5G C6G C7G O1G 180.0(2) . . . . ?
C5G C6G C7G O1H 170.2(7) . . . . ?
C5G C6G C7G C8G 53.55(16) . . . . ?
C6A C1A C2A C3A 0.6(3) . . . . ?
C6A C7A C8A C9A -62.9(4) . . . . ?
C6A C7A C8A C13A 172.3(3) . . . . ?
C6A C7B C8B C9B 32.0(7) . . . . ?
C6A C7B C8B C13B 156.0(4) . . . . ?
C6C C1C C2C C3C -57.79(18) . . . . ?
C6C C7C C8C C9C -70.70(19) . . . . ?
C6C C7C C8C C13C 109.37(16) . . . . ?
C6G C1G C2G C3G 56.83(17) . . . . ?
C6G C7G C8G C9G 71.47(18) . . . . ?
C6G C7G C8G C13G -109.85(15) . . . . ?
C7A C8A C9A C10A -176.8(4) . . . . ?
C7A C8A C13A C12A 178.8(3) . . . . ?
C7B C8B C9B C10B -179.3(4) . . . . ?
C7B C8B C13B C12B 176.8(4) . . . . ?
C7C C8C C9C Cl1C 2.6(2) . . . . ?
C7C C8C C9C Cl1D -18(3) . . . . ?
C7C C8C C9C C10C -178.13(16) . . . . ?
C7C C8C C13C Cl2C -1.4(2) . . . . ?
C7C C8C C13C Cl2D 14.0(19) . . . . ?
C7C C8C C13C C12C 179.19(15) . . . . ?
C7G C8G C9G Cl1G -1.5(2) . . . . ?
C7G C8G C9G Cl1H -5.2(3) . . . . ?
C7G C8G C9G C10G 177.35(15) . . . . ?
C7G C8G C13G Cl2G -0.3(3) . . . . ?
C7G C8G C13G Cl2H 3.6(8) . . . . ?
C7G C8G C13G C12G -178.34(15) . . . . ?
C8A C9A C10A C11A 56.0(3) . . . . ?
C8B C9B C10B C11B -57.5(4) . . . . ?
C8C C9C C10C C11C -1.8(3) . . . . ?
C8G C9G C10G C11G 1.4(3) . . . . ?
C9A C8A C13A C12A 52.6(3) . . . . ?
C9A C10A C11A C12A -57.6(3) . . . . ?
C9B C8B C13B C12B -56.8(4) . . . . ?
C9B C10B C11B C12B 55.8(4) . . . . ?
C9C C8C C13C Cl2C 178.69(12) . . . . ?
C9C C8C C13C Cl2D -165.9(19) . . . . ?
C9C C8C C13C C12C -0.7(2) . . . . ?
C9C C10C C11C C12C 0.6(3) . . . . ?
C9G C8G C13G Cl2G 178.5(3) . . . . ?
C9G C8G C13G Cl2H -177.6(7) . . . . ?
C9G C8G C13G C12G 0.4(2) . . . . ?
C9G C10G C11G C12G -0.4(3) . . . . ?
C10A C11A C12A C13A 57.2(3) . . . . ?
C10B C11B C12B C13B -53.7(4) . . . . ?
C10C C11C C12C C13C 0.4(3) . . . . ?
C10G C11G C12G C13G -0.5(3) . . . . ?
C11A C12A C13A C8A -55.1(3) . . . . ?
C11B C12B C13B C8B 54.4(4) . . . . ?
C11C C12C C13C Cl2C -179.79(16) . . . . ?
C11C C12C C13C Cl2D 162(3) . . . . ?
C11C C12C C13C C8C -0.3(3) . . . . ?
C11G C12G C13G Cl2G -177.6(3) . . . . ?
C11G C12G C13G Cl2H 178.5(8) . . . . ?
C11G C12G C13G C8G 0.5(3) . . . . ?
C13A C8A C9A C10A -53.1(3) . . . . ?
C13B C8B C9B C10B 57.6(4) . . . . ?
C13C C8C C9C Cl1C -177.48(12) . . . . ?
C13C C8C C9C Cl1D 162(3) . . . . ?
C13C C8C C9C C10C 1.8(2) . . . . ?
C13G C8G C9G Cl1G 179.78(12) . . . . ?
C13G C8G C9G Cl1H 176.1(3) . . . . ?
C13G C8G C9G C10G -1.4(2) . . . . ?
Cl1E C9E C10E C11E 176.57(14) . . . . ?
Cl1F C9E C10E C11E -173.5(2) . . . . ?
O1E C7E C8E C9E 51.8(2) . . . . ?
O1E C7E C8E C13E -123.39(19) . . . . ?
O1F C7E C8E C9E 64.2(5) . . . . ?
O1F C7E C8E C13E -111.0(5) . . . . ?
C1E C2E C3E C4E 53.3(3) . . . . ?
C1E C2E C3F C4F 63.0(8) . . . . ?
C1E C6E C7E O1E 75.0(2) . . . . ?
C1E C6E C7E O1F 62.8(5) . . . . ?
C1E C6E C7E C8E -165.17(13) . . . . ?
C2E C1E C6E C5E 51.9(2) . . . . ?
C2E C1E C6E C5F 69.0(4) . . . . ?
C2E C1E C6E C7E -178.10(13) . . . . ?
C2E C3E C4E C5E -56.1(3) . . . . ?
C2E C3F C4F C5F -62.8(10) . . . . ?
C3E C4E C5E C6E 56.0(3) . . . . ?
C3F C4F C5F C6E 64.8(9) . . . . ?
C4E C5E C6E C1E -55.3(3) . . . . ?
C4E C5E C6E C7E 177.5(2) . . . . ?
C4F C5F C6E C1E -62.0(7) . . . . ?
C4F C5F C6E C7E -176.2(6) . . . . ?
C5E C6E C7E O1E -155.6(3) . . . . ?
C5E C6E C7E C8E -35.7(3) . . . . ?
C5F C6E C7E O1F 170.6(7) . . . . ?
C5F C6E C7E C8E -57.3(5) . . . . ?
C6E C1E C2E C3E -49.9(3) . . . . ?
C6E C1E C2E C3F -72.4(6) . . . . ?
C6E C7E C8E C9E -68.49(18) . . . . ?
C6E C7E C8E C13E 116.29(15) . . . . ?
C7E C8E C9E Cl1E 9.6(2) . . . . ?
C7E C8E C9E Cl1F -0.5(3) . . . . ?
C7E C8E C9E C10E -173.99(14) . . . . ?
C7E C8E C13E Cl2E -3.3(2) . . . . ?
C7E C8E C13E Cl2F -14.7(3) . . . . ?
C7E C8E C13E C12E 173.79(13) . . . . ?
C8E C9E C10E C11E 0.0(2) . . . . ?
C9E C8E C13E Cl2E -178.92(13) . . . . ?
C9E C8E C13E Cl2F 169.8(2) . . . . ?
C9E C8E C13E C12E -1.8(2) . . . . ?
C9E C10E C11E C12E -1.4(2) . . . . ?
C10E C11E C12E C13E 1.2(2) . . . . ?
C11E C12E C13E Cl2E 177.71(14) . . . . ?
C11E C12E C13E Cl2F -171.5(2) . . . . ?
C11E C12E C13E C8E 0.5(2) . . . . ?
C13E C8E C9E Cl1E -174.86(13) . . . . ?
C13E C8E C9E Cl1F 175.1(2) . . . . ?
C13E C8E C9E C10E 1.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_kaz273
_database_code_depnum_ccdc_archive 'CCDC 2336549'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-07-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H22 B F N2 O'
_chemical_formula_sum            'C17 H22 B F N2 O'
_chemical_formula_weight         300.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H28N2O
_chemical_oxdiff_usercomment     kaz273
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.16710(10)
_cell_length_b                   10.20320(10)
_cell_length_c                   22.0229(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3183.41(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15990
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      77.6440
_cell_measurement_theta_min      3.9920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.5
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.583
_diffrn_reflns_theta_min         4.015
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -22.00   0.50    1.03    --  -86.25  44.00  48.00   56
  2  ω    -70.00  24.00   0.50    0.26    --  -48.70  76.00-141.00  188
  3  ω   -120.00 -66.00   0.50    0.26    --  -48.70-137.00-146.00  108
  4  ω    -20.00  26.00   0.50    0.26    --  -48.70  19.00 120.00   92
  5  ω     98.00 134.00   0.50    1.03    --  107.75  15.00  60.00   72
  6  ω     99.00 155.00   0.50    1.03    --  107.75  44.00  48.00  112
  7  ω    108.00 134.00   0.50    1.03    --  107.75  50.00 146.87   52
  8  ω    139.00 164.00   0.50    1.03    --  107.75  50.00 146.87   50
  9  ω    124.00 150.00   0.50    1.03    --  107.75  76.00-141.00   52
 10  ω    100.00 141.00   0.50    1.03    --  107.75  30.00-120.00   82
 11  ω     36.00  71.00   0.50    1.03    --  107.75 -61.00-120.00   70
 12  ω     70.00 101.00   0.50    1.03    --  107.75 -77.00   0.00   62
 13  ω     36.00  67.00   0.50    1.03    --  107.75 -77.00   0.00   62
 14  ω     36.00  62.00   0.50    1.03    --  107.75 -61.00 -30.00   52
 15  ω     61.00  96.00   0.50    1.03    --  107.75 -77.00  30.00   70
 16  ω     77.00 103.00   0.50    1.03    --  107.75 -77.00  60.00   52
 17  ω     57.00  83.00   0.50    1.03    --  107.75 -76.00  91.00   52
 18  ω     36.00  71.00   0.50    1.03    --  107.75 -77.00 150.00   70
 19  ω     36.00  61.00   0.50    1.03    --  107.75 -61.00  90.00   50
 20  ω     39.00  70.00   0.50    1.03    --  107.75 -61.00  60.00   62
 21  ω     56.00  81.00   0.50    1.03    --  107.75-137.00-146.00   50
 22  ω     51.00  77.00   0.50    1.03    --  107.75-125.00 -60.00   52
 23  ω     86.00 111.00   0.50    1.03    --  107.75-125.00 -60.00   50
 24  ω     56.00  82.00   0.50    1.03    --  107.75 -95.00 -90.00   52
 25  ω     53.00 109.00   0.50    1.03    --  107.75-115.00 -26.58  112
 26  ω     40.00  66.00   0.50    1.03    --  107.75 -87.00-159.06   52
 27  ω     91.00 118.00   0.50    1.03    --  107.75-133.00  30.00   54
 28  ω     49.00  75.00   0.50    1.03    --  107.75 -95.00 150.00   52
 29  ω     65.00 102.00   0.50    1.03    --  107.75 -95.00  90.00   74
 30  ω     49.00  75.00   0.50    1.03    --  107.75-133.00  30.00   52
 31  ω     89.00 124.00   0.50    1.03    --  107.75 -87.00-159.06   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0819276000
_diffrn_orient_matrix_UB_12      -0.0746576000
_diffrn_orient_matrix_UB_13      -0.0302715000
_diffrn_orient_matrix_UB_21      -0.0383567000
_diffrn_orient_matrix_UB_22      0.0378572000
_diffrn_orient_matrix_UB_23      -0.0630062000
_diffrn_orient_matrix_UB_31      0.0603434000
_diffrn_orient_matrix_UB_32      0.1257796000
_diffrn_orient_matrix_UB_33      0.0009313000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3242
_reflns_number_total             3379
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.030
_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)+(0.0433P)²+1.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.49784(4) 0.95514(6) 0.66580(3) 0.02263(15) Uani 1 1 d . . . . .
O1 O 0.47288(5) 0.74100(7) 0.62696(3) 0.01901(16) Uani 1 1 d . . . . .
N1 N 0.38183(6) 0.80386(8) 0.70918(4) 0.01771(18) Uani 1 1 d . . . . .
N2 N 0.39538(6) 0.66676(8) 0.71066(4) 0.01912(18) Uani 1 1 d . . . . .
C1 C 0.44686(7) 0.64336(10) 0.66262(4) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.47679(7) 0.51040(10) 0.64559(5) 0.0187(2) Uani 1 1 d . . . . .
C3 C 0.52929(7) 0.49279(10) 0.59246(5) 0.0212(2) Uani 1 1 d . . . . .
H3 H 0.544602 0.565994 0.567691 0.025 Uiso 1 1 calc R U . . .
C4 C 0.55901(7) 0.36813(11) 0.57597(5) 0.0248(2) Uani 1 1 d . . . . .
H4 H 0.594795 0.356100 0.539915 0.030 Uiso 1 1 calc R U . . .
C5 C 0.53653(8) 0.26098(10) 0.61204(5) 0.0258(2) Uani 1 1 d . . . . .
H5 H 0.557742 0.175941 0.600981 0.031 Uiso 1 1 calc R U . . .
C6 C 0.48297(8) 0.27814(11) 0.66439(5) 0.0265(2) Uani 1 1 d . . . . .
H6 H 0.466851 0.204553 0.688701 0.032 Uiso 1 1 calc R U . . .
C7 C 0.45303(7) 0.40239(10) 0.68117(5) 0.0231(2) Uani 1 1 d . . . . .
H7 H 0.416356 0.413844 0.716890 0.028 Uiso 1 1 calc R U . . .
C8 C 0.33722(7) 0.86065(10) 0.75197(4) 0.0193(2) Uani 1 1 d . . . . .
C9 C 0.31236(7) 1.00239(10) 0.76073(5) 0.0217(2) Uani 1 1 d . . . . .
H9A H 0.268623 1.037598 0.729690 0.026 Uiso 1 1 calc R U . . .
H9B H 0.367620 1.060556 0.766265 0.026 Uiso 1 1 calc R U . . .
C10 C 0.26346(8) 0.96162(11) 0.82098(5) 0.0273(2) Uani 1 1 d . . . . .
H10A H 0.194388 0.976313 0.820970 0.033 Uiso 1 1 calc R U . . .
H10B H 0.292894 1.000505 0.857559 0.033 Uiso 1 1 calc R U . . .
C11 C 0.29192(8) 0.81598(11) 0.80995(5) 0.0239(2) Uani 1 1 d . . . . .
H11A H 0.336899 0.780689 0.840219 0.029 Uiso 1 1 calc R U . . .
H11B H 0.237707 0.756081 0.804076 0.029 Uiso 1 1 calc R U . . .
C12 C 0.35183(7) 0.92105(10) 0.60190(4) 0.0189(2) Uani 1 1 d . . . . .
H12 H 0.324040 1.002858 0.619392 0.023 Uiso 1 1 calc R U . . .
C13 C 0.27091(7) 0.82403(11) 0.58974(5) 0.0233(2) Uani 1 1 d . . . . .
H13A H 0.297838 0.738988 0.576769 0.028 Uiso 1 1 calc R U . . .
H13B H 0.235565 0.809246 0.627910 0.028 Uiso 1 1 calc R U . . .
C14 C 0.20272(7) 0.87304(12) 0.54093(5) 0.0266(2) Uani 1 1 d . . . . .
H14A H 0.153862 0.805623 0.533357 0.032 Uiso 1 1 calc R U . . .
H14B H 0.170725 0.953397 0.555454 0.032 Uiso 1 1 calc R U . . .
C15 C 0.25493(7) 0.90269(11) 0.48188(5) 0.0246(2) Uani 1 1 d . . . . .
H15A H 0.209840 0.936861 0.451399 0.030 Uiso 1 1 calc R U . . .
H15B H 0.282963 0.820995 0.465660 0.030 Uiso 1 1 calc R U . . .
C16 C 0.33269(8) 1.00355(11) 0.49277(5) 0.0245(2) Uani 1 1 d . . . . .
H16A H 0.303995 1.087773 0.505320 0.029 Uiso 1 1 calc R U . . .
H16B H 0.367766 1.018550 0.454515 0.029 Uiso 1 1 calc R U . . .
C17 C 0.40112(7) 0.95690(10) 0.54196(4) 0.0209(2) Uani 1 1 d . . . . .
H17A H 0.447905 1.026920 0.549880 0.025 Uiso 1 1 calc R U . . .
H17B H 0.435779 0.879259 0.526799 0.025 Uiso 1 1 calc R U . . .
B1 B 0.42806(8) 0.86575(11) 0.64894(5) 0.0182(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3953(13) . ?
O1 C1 1.3211(12) . ?
O1 B1 1.5025(12) . ?
N1 N2 1.4123(11) . ?
N1 C8 1.2741(13) . ?
N1 B1 1.6088(13) . ?
N2 C1 1.3069(13) . ?
C1 C2 1.4700(13) . ?
C2 C3 1.3982(14) . ?
C2 C7 1.3934(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3881(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3884(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3912(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3870(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.5009(14) . ?
C8 C11 1.5000(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5536(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5588(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.5381(14) . ?
C12 C17 1.5376(13) . ?
C12 B1 1.5992(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5293(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5265(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5265(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5297(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 109.24(7) . . ?
N2 N1 B1 110.64(7) . . ?
C8 N1 N2 120.06(8) . . ?
C8 N1 B1 129.30(9) . . ?
C1 N2 N1 103.78(8) . . ?
O1 C1 C2 117.64(8) . . ?
N2 C1 O1 119.94(9) . . ?
N2 C1 C2 122.42(9) . . ?
C3 C2 C1 119.05(9) . . ?
C7 C2 C1 121.12(9) . . ?
C7 C2 C3 119.83(9) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.87(10) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.15(10) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.01(10) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.17(10) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 119.95(10) . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C9 130.52(9) . . ?
N1 C8 C11 134.72(10) . . ?
C11 C8 C9 94.76(8) . . ?
C8 C9 H9A 114.1 . . ?
C8 C9 H9B 114.1 . . ?
C8 C9 C10 87.50(8) . . ?
H9A C9 H9B 111.3 . . ?
C10 C9 H9A 114.1 . . ?
C10 C9 H9B 114.1 . . ?
C9 C10 H10A 113.6 . . ?
C9 C10 H10B 113.6 . . ?
C9 C10 C11 90.39(8) . . ?
H10A C10 H10B 110.8 . . ?
C11 C10 H10A 113.6 . . ?
C11 C10 H10B 113.6 . . ?
C8 C11 C10 87.34(8) . . ?
C8 C11 H11A 114.1 . . ?
C8 C11 H11B 114.1 . . ?
C10 C11 H11A 114.1 . . ?
C10 C11 H11B 114.1 . . ?
H11A C11 H11B 111.3 . . ?
C13 C12 H12 108.1 . . ?
C13 C12 B1 112.90(8) . . ?
C17 C12 H12 108.1 . . ?
C17 C12 C13 110.00(8) . . ?
C17 C12 B1 109.47(8) . . ?
B1 C12 H12 108.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 112.51(9) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 110.95(8) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C14 C15 C16 110.45(9) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C15 C16 C17 111.03(9) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C12 C17 H17A 108.9 . . ?
C12 C17 H17B 108.9 . . ?
C16 C17 C12 113.22(8) . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
F1 B1 O1 109.88(8) . . ?
F1 B1 N1 108.99(8) . . ?
F1 B1 C12 114.85(8) . . ?
O1 B1 N1 96.03(7) . . ?
O1 B1 C12 112.07(8) . . ?
C12 B1 N1 113.44(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
O1 C1 C2 C3 -1.20(13) . . . . ?
O1 C1 C2 C7 179.34(9) . . . . ?
N1 N2 C1 O1 0.25(11) . . . . ?
N1 N2 C1 C2 -178.91(8) . . . . ?
N1 C8 C9 C10 179.69(11) . . . . ?
N1 C8 C11 C10 -179.71(12) . . . . ?
N2 N1 C8 C9 -179.01(10) . . . . ?
N2 N1 C8 C11 1.27(17) . . . . ?
N2 N1 B1 F1 -119.09(8) . . . . ?
N2 N1 B1 O1 -5.64(9) . . . . ?
N2 N1 B1 C12 111.59(9) . . . . ?
N2 C1 C2 C3 177.97(9) . . . . ?
N2 C1 C2 C7 -1.49(15) . . . . ?
C1 O1 B1 F1 118.25(9) . . . . ?
C1 O1 B1 N1 5.53(9) . . . . ?
C1 O1 B1 C12 -112.79(9) . . . . ?
C1 C2 C3 C4 179.34(9) . . . . ?
C1 C2 C7 C6 -179.36(10) . . . . ?
C2 C3 C4 C5 0.13(16) . . . . ?
C3 C2 C7 C6 1.18(15) . . . . ?
C3 C4 C5 C6 0.93(16) . . . . ?
C4 C5 C6 C7 -0.94(17) . . . . ?
C5 C6 C7 C2 -0.12(16) . . . . ?
C7 C2 C3 C4 -1.19(15) . . . . ?
C8 N1 N2 C1 -176.82(9) . . . . ?
C8 N1 B1 F1 61.52(13) . . . . ?
C8 N1 B1 O1 174.97(9) . . . . ?
C8 N1 B1 C12 -67.80(13) . . . . ?
C8 C9 C10 C11 0.49(8) . . . . ?
C9 C8 C11 C10 0.50(8) . . . . ?
C9 C10 C11 C8 -0.49(8) . . . . ?
C11 C8 C9 C10 -0.51(8) . . . . ?
C12 C13 C14 C15 56.42(12) . . . . ?
C13 C12 C17 C16 52.12(11) . . . . ?
C13 C12 B1 F1 -174.13(8) . . . . ?
C13 C12 B1 O1 59.56(11) . . . . ?
C13 C12 B1 N1 -47.85(11) . . . . ?
C13 C14 C15 C16 -57.44(12) . . . . ?
C14 C15 C16 C17 56.45(11) . . . . ?
C15 C16 C17 C12 -54.78(12) . . . . ?
C17 C12 C13 C14 -52.76(11) . . . . ?
C17 C12 B1 F1 62.97(11) . . . . ?
C17 C12 B1 O1 -63.33(10) . . . . ?
C17 C12 B1 N1 -170.75(8) . . . . ?
B1 O1 C1 N2 -4.36(12) . . . . ?
B1 O1 C1 C2 174.84(8) . . . . ?
B1 N1 N2 C1 3.73(10) . . . . ?
B1 N1 C8 C9 0.33(17) . . . . ?
B1 N1 C8 C11 -179.39(10) . . . . ?
B1 C12 C13 C14 -175.36(8) . . . . ?
B1 C12 C17 C16 176.72(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.781
####################################################################### 
# 
# 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_km1797-11
_database_code_depnum_ccdc_archive 'CCDC 2336548'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2024-01-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     KM1797.1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.13130(10)
_cell_length_b                   13.6328(2)
_cell_length_c                   9.04630(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1126.13(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12852
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      80.4710
_cell_measurement_theta_min      3.2330
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0933
2 1 -2 0.1638
-1 0 -2 0.1138
0 0 1 0.0983
2 1 2 0.1051
-2 -1 2 0.1408
2 1 -1 0.1650
-1 -1 -2 0.1237
1 1 1 0.1150
1 0 -2 0.1555
-1 -2 -2 0.1320
-1 1 2 0.0939
1 -2 -2 0.1668
0 -1 0 0.0991
0 1 0 0.0973
-1 1 1 0.0908
1 -1 -1 0.1615
-2 1 0 0.1487
-2 2 -1 0.1476
4 -5 3 0.0514

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
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
0.9986 0.0037 0.9996 0.0484 0.2342 -0.0140
1.9988 1.0014 -1.9988 -0.0137 -0.0310 -0.4910
-0.9979 -0.0051 -1.9988 -0.0490 -0.3643 -0.0957
-0.0007 0.0013 0.9992 0.0006 0.1301 0.1097
1.9960 1.0068 1.9981 -0.0114 0.4895 -0.0523
-1.9988 -1.0014 1.9988 0.0137 0.0310 0.4910
1.9981 1.0027 -0.9996 -0.0131 0.0992 -0.3813
-0.9967 -1.0044 -1.9978 0.0592 -0.3854 -0.0714
0.9974 1.0030 0.9985 -0.0598 0.2553 -0.0383
1.0007 -0.0003 -1.9981 0.0467 -0.1561 -0.3431
-0.9954 -2.0036 -1.9967 0.1675 -0.4065 -0.0471
-1.0019 0.9996 1.9970 -0.1549 0.1772 0.3187
1.0032 -1.9988 -1.9960 0.2631 -0.1983 -0.2944
0.0012 -0.9993 0.0011 0.1082 -0.0211 0.0243
-0.0012 0.9993 -0.0011 -0.1082 0.0211 -0.0243
-1.0012 0.9982 0.9978 -0.1555 0.0471 0.2090
1.0012 -0.9982 -0.9978 0.1555 -0.0471 -0.2090
-1.9998 0.9945 -0.0018 -0.2039 -0.1871 0.2230
-2.0004 1.9924 -1.0021 -0.3128 -0.2961 0.0890
4.0013 -4.9827 3.0044 0.7344 0.7012 -0.0440

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14533
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         81.093
_diffrn_reflns_theta_min         3.242
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  30.00   0.50    0.10    --  -44.12  57.00 135.00  188
  2  ω    -81.00 -22.00   0.50    0.40    --  -96.00  67.00 -23.00  118
  3  ω    -51.00 -21.00   0.50    0.40    --  -96.00  45.00 -30.00   60
  4  ω   -118.00 -21.00   0.50    0.10    --  -44.12 -67.00-157.00  194
  5  ω   -118.00 -24.00   0.50    0.10    --  -44.12 -57.00  -5.00  188
  6  ω     45.00  71.00   0.50    0.40    --  117.50 -61.00 -30.00   52
  7  ω     45.00 105.00   0.50    0.40    --  117.50 -77.00 -90.00  120
  8  ω     45.00  81.00   0.50    0.40    --  117.50 -67.00-157.00   72
  9  ω    103.00 178.00   0.50    0.40    --  117.50 110.00-143.00  150
 10  ω     95.00 178.00   0.50    0.40    --  117.50 125.00 -90.00  166
 11  ω     45.00 105.00   0.50    0.40    --  117.50 -77.00 120.00  120
 12  ω     45.00  71.00   0.50    0.40    --  117.50 -61.00  60.00   52
 13  ω     45.00  71.00   0.50    0.40    --  117.50 -61.00 -90.00   52
 14  ω     45.00 105.00   0.50    0.40    --  117.50 -95.00-150.00  120
 15  ω     34.00  94.00   0.50    0.10    --   44.12-125.00-180.00  120
 16  ω     47.00 111.00   0.50    0.40    --  117.50-125.00-180.00  128
 17  ω     47.00 111.00   0.50    0.40    --  117.50-125.00-150.00  128
 18  ω     47.00 111.00   0.50    0.40    --  117.50-125.00 -30.00  128
 19  ω     45.00 105.00   0.50    0.40    --  117.50 -95.00 -90.00  120
 20  ω     45.00 105.00   0.50    0.40    --  117.50 -95.00 -30.00  120
 21  ω     46.00 108.00   0.50    0.40    --  117.50-110.00 121.00  124
 22  ω     86.00 160.00   0.50    0.40    --  117.50  15.00  90.00  148
 23  ω     91.00 178.00   0.50    0.40    --  117.50  77.00  60.00  174
 24  ω     91.00 178.00   0.50    0.40    --  117.50  77.00  60.00  174
 25  ω     98.00 178.00   0.50    0.40    --  117.50  45.00  60.00  160
 26  ω     98.00 178.00   0.50    0.40    --  117.50  57.00 135.00  160
 27  ω     86.00 178.00   0.50    0.40    --  117.50  15.00 150.00  184
 28  ω     95.00 178.00   0.50    0.40    --  117.50  67.00 -23.00  166
 29  ω     91.00 178.00   0.50    0.40    --  117.50  77.00 -90.00  174
 30  ω     91.00 178.00   0.50    0.40    --  117.50  77.00 -90.00  174
 31  ω     98.00 178.00   0.50    0.40    --  117.50  30.00-150.00  160
 32  ω     86.00 178.00   0.50    0.40    --  117.50  15.00 -60.00  184
 33  ω     86.00 160.00   0.50    0.40    --  117.50  15.00  90.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0481398000
_diffrn_orient_matrix_UB_12      -0.1082620000
_diffrn_orient_matrix_UB_13      0.0007725000
_diffrn_orient_matrix_UB_21      0.1040586000
_diffrn_orient_matrix_UB_22      0.0213781000
_diffrn_orient_matrix_UB_23      0.1302556000
_diffrn_orient_matrix_UB_31      -0.1237319000
_diffrn_orient_matrix_UB_32      -0.0243665000
_diffrn_orient_matrix_UB_33      0.1097237000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2350
_reflns_number_total             2367
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.062
_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)+(0.0343P)²+0.2879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30870(15) 0.42175(9) 0.30376(14) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.318429 0.389032 0.225693 0.036 Uiso 1 1 calc R U . . .
O2 O 0.40060(13) 0.62393(8) 0.39376(13) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.68765(14) 0.67145(9) 0.53808(14) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.729758 0.642697 0.467809 0.031 Uiso 1 1 calc R U . . .
C1 C 0.23221(19) 0.51144(12) 0.2717(2) 0.0238(4) Uani 1 1 d . . . . .
H1A H 0.158747 0.524026 0.349907 0.029 Uiso 1 1 calc R U . . .
H1B H 0.179658 0.504721 0.176499 0.029 Uiso 1 1 calc R U . . .
C2 C 0.33530(17) 0.59579(12) 0.2630(2) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.3866(2) 0.65061(12) 0.15057(19) 0.0206(3) Uani 1 1 d . . . . .
H3A H 0.358725 0.645961 0.049643 0.025 Uiso 1 1 calc R U . . .
C4 C 0.49117(18) 0.71720(12) 0.2122(2) 0.0189(3) Uani 1 1 d . . . . .
H4 H 0.546442 0.765113 0.160200 0.023 Uiso 1 1 calc R U . . .
C5 C 0.49591(17) 0.69862(11) 0.35854(19) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.58538(16) 0.74166(12) 0.48032(19) 0.0163(3) Uani 1 1 d . . . . .
H6 H 0.643101 0.797238 0.437765 0.020 Uiso 1 1 calc R U . . .
C7 C 0.49544(17) 0.78229(12) 0.60960(19) 0.0157(3) Uani 1 1 d . . . . .
H7 H 0.442472 0.726630 0.657828 0.019 Uiso 1 1 calc R U . . .
C8 C 0.59673(18) 0.83012(13) 0.7245(2) 0.0199(3) Uani 1 1 d . . . . .
H8A H 0.661495 0.779325 0.767448 0.024 Uiso 1 1 calc R U . . .
H8B H 0.659422 0.879326 0.674774 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5111(2) 0.88008(13) 0.8489(2) 0.0236(4) Uani 1 1 d . . . . .
H9A H 0.458162 0.829720 0.906855 0.028 Uiso 1 1 calc R U . . .
H9B H 0.580463 0.913688 0.916044 0.028 Uiso 1 1 calc R U . . .
C10 C 0.40166(19) 0.95450(13) 0.7887(2) 0.0233(4) Uani 1 1 d . . . . .
H10A H 0.344251 0.982624 0.871275 0.028 Uiso 1 1 calc R U . . .
H10B H 0.454893 1.008655 0.739399 0.028 Uiso 1 1 calc R U . . .
C11 C 0.29854(19) 0.90564(13) 0.6786(2) 0.0215(3) Uani 1 1 d . . . . .
H11A H 0.231522 0.955601 0.637025 0.026 Uiso 1 1 calc R U . . .
H11B H 0.238430 0.856089 0.730767 0.026 Uiso 1 1 calc R U . . .
C12 C 0.38216(19) 0.85598(12) 0.55262(18) 0.0192(3) Uani 1 1 d . . . . .
H12A H 0.432412 0.906690 0.492935 0.023 Uiso 1 1 calc R U . . .
H12B H 0.311727 0.821604 0.487505 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C1 1.438(2) . ?
O2 C2 1.379(2) . ?
O2 C5 1.3769(19) . ?
O3 H3 0.8400 . ?
O3 C6 1.4358(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.488(2) . ?
C2 C3 1.346(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.430(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.349(2) . ?
C5 C6 1.492(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.533(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.537(2) . ?
C7 C12 1.531(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.525(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.530(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C5 O2 C2 106.29(13) . . ?
C6 O3 H3 109.5 . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.13(14) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
O2 C2 C1 116.32(16) . . ?
C3 C2 O2 110.07(14) . . ?
C3 C2 C1 133.53(17) . . ?
C2 C3 H3A 126.6 . . ?
C2 C3 C4 106.86(15) . . ?
C4 C3 H3A 126.6 . . ?
C3 C4 H4 126.7 . . ?
C5 C4 C3 106.54(16) . . ?
C5 C4 H4 126.7 . . ?
O2 C5 C6 117.79(14) . . ?
C4 C5 O2 110.23(15) . . ?
C4 C5 C6 131.96(16) . . ?
O3 C6 C5 111.27(13) . . ?
O3 C6 H6 107.6 . . ?
O3 C6 C7 108.16(13) . . ?
C5 C6 H6 107.6 . . ?
C5 C6 C7 114.34(13) . . ?
C7 C6 H6 107.6 . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 110.30(13) . . ?
C8 C7 H7 108.5 . . ?
C12 C7 C6 110.01(14) . . ?
C12 C7 H7 108.5 . . ?
C12 C7 C8 110.85(14) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.26(14) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.62(16) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.34(14) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C10 C11 C12 111.83(14) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C7 C12 H12A 109.2 . . ?
C7 C12 H12B 109.2 . . ?
C11 C12 C7 112.12(14) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.84 1.89 2.7188(17) 170.0 2_664 yes
O3 H3 O1 0.84 1.87 2.7073(17) 175.3 3_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 -68.50(19) . . . . ?
O1 C1 C2 C3 107.8(2) . . . . ?
O2 C2 C3 C4 0.35(19) . . . . ?
O2 C5 C6 O3 66.01(17) . . . . ?
O2 C5 C6 C7 -56.90(18) . . . . ?
O3 C6 C7 C8 58.70(17) . . . . ?
O3 C6 C7 C12 -178.71(13) . . . . ?
C1 C2 C3 C4 -176.16(17) . . . . ?
C2 O2 C5 C4 0.11(18) . . . . ?
C2 O2 C5 C6 -178.40(13) . . . . ?
C2 C3 C4 C5 -0.28(19) . . . . ?
C3 C4 C5 O2 0.10(19) . . . . ?
C3 C4 C5 C6 178.33(16) . . . . ?
C4 C5 C6 O3 -112.1(2) . . . . ?
C4 C5 C6 C7 124.98(19) . . . . ?
C5 O2 C2 C1 176.89(13) . . . . ?
C5 O2 C2 C3 -0.29(18) . . . . ?
C5 C6 C7 C8 -176.73(13) . . . . ?
C5 C6 C7 C12 -54.14(18) . . . . ?
C6 C7 C8 C9 174.77(13) . . . . ?
C6 C7 C12 C11 -174.89(14) . . . . ?
C7 C8 C9 C10 -55.01(19) . . . . ?
C8 C7 C12 C11 -52.63(19) . . . . ?
C8 C9 C10 C11 56.01(19) . . . . ?
C9 C10 C11 C12 -56.2(2) . . . . ?
C10 C11 C12 C7 55.21(19) . . . . ?
C12 C7 C8 C9 52.67(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.718
####################################################################### 
# 
# 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_kaz280
_database_code_depnum_ccdc_archive 'CCDC 2336550'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 B F N2 O'
_chemical_formula_sum            'C19 H26 B F N2 O'
_chemical_formula_weight         328.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H24N2O
_chemical_oxdiff_usercomment     kaz280
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.52990(10)
_cell_length_b                   11.13290(10)
_cell_length_c                   18.1267(2)
_cell_angle_alpha                101.2000(10)
_cell_angle_beta                 94.3790(10)
_cell_angle_gamma                105.7310(10)
_cell_volume                     1798.84(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35053
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      77.4410
_cell_measurement_theta_min      2.5020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.5
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47208
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.888
_diffrn_reflns_theta_min         2.508
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -3.00   0.50    0.15    --  -48.70 112.00 -52.00  158
  2  ω     25.00  85.00   0.50    0.15    --   48.70-112.00-145.00  120
  3  ω   -154.00 -81.00   0.50    0.60    --  -86.25-112.00-145.00  146
  4  ω    -83.00 -18.00   0.50    0.60    --  -86.25 112.00 -52.00  130
  5  ω     40.00 109.00   0.50    0.60    --  107.75-112.00-145.00  138
  6  ω    103.00 176.00   0.50    0.60    --  107.75 112.00 -52.00  146
  7  ω   -118.00 -73.00   0.50    0.15    --  -48.70-125.00   0.00   90
  8  ω    -63.00  24.00   0.50    0.15    --  -48.70  57.00 -60.00  174
  9  ω    -26.00  26.00   0.50    0.15    --  -48.70  19.00  90.00  104
 10  ω    -26.00  26.00   0.50    0.15    --  -48.70  19.00   0.00  104
 11  ω   -118.00 -73.00   0.50    0.15    --  -48.70-125.00 -30.00   90
 12  ω    -26.00  26.00   0.50    0.15    --  -48.70  19.00-150.00  104
 13  ω    -25.00  26.00   0.50    0.15    --   48.70 -19.00 120.00  102
 14  ω    -51.00 -14.00   0.50    0.60    --  -86.25  45.00-120.00   74
 15  ω   -158.00 -72.00   0.50    0.60    --  -86.25 -59.00 -75.62  172
 16  ω    -51.00 -14.00   0.50    0.60    --  -86.25  45.00 -90.00   74
 17  ω     39.00 111.00   0.50    0.60    --  107.75-125.00  90.00  144
 18  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00-120.00  138
 19  ω     38.00 107.00   0.50    0.60    --  107.75-104.00 119.22  138
 20  ω     39.00 111.00   0.50    0.60    --  107.75-125.00  30.00  144
 21  ω     97.00 178.00   0.50    0.60    --  107.75  45.00  90.00  162
 22  ω     93.00 178.00   0.50    0.60    --  107.75  61.00   0.00  170
 23  ω     36.00  71.00   0.50    0.60    --  107.75 -61.00   0.00   70
 24  ω     93.00 178.00   0.50    0.60    --  107.75  61.00-150.00  170
 25  ω     79.00 167.00   0.50    0.60    --  107.75 148.00  56.67  176
 26  ω     97.00 178.00   0.50    0.60    --  107.75  45.00-120.00  162
 27  ω     95.00 177.00   0.50    0.60    --  107.75 125.00 -90.00  164
 28  ω     97.00 178.00   0.50    0.60    --  107.75  15.00-180.00  162
 29  ω    124.00 173.00   0.50    0.60    --  107.75  77.00  60.00   98
 30  ω     65.00 107.00   0.50    0.60    --  107.75-125.00 120.00   84
 31  ω     79.00 105.00   0.50    0.60    --  107.75 -95.00-150.00   52
 32  ω     50.00 110.00   0.50    0.60    --  107.75-125.00-180.00  120
 33  ω     57.00  83.00   0.50    0.60    --  107.75 -83.00  -7.10   52
 34  ω    130.00 176.00   0.50    0.60    --  107.75  30.00 120.00   92
 35  ω     38.00  70.00   0.50    0.60    --  107.75 -61.00 120.00   64
 36  ω     39.00  71.00   0.50    0.60    --  107.75 -61.00  90.00   64
 37  ω    116.00 149.00   0.50    0.60    --  107.75 125.00-180.00   66
 38  ω     40.00  79.00   0.50    0.60    --  107.75 -82.00  10.95   78
 39  ω     41.00  71.00   0.50    0.60    --  107.75 -61.00 -60.00   60
 40  ω     36.00  61.00   0.50    0.60    --  107.75 -61.00 -90.00   50
 41  ω     88.00 132.00   0.50    0.60    --  107.75 -82.00  10.95   88
 42  ω     50.00  84.00   0.50    0.60    --  107.75 -82.00 107.06   68
 43  ω     98.00 124.00   0.50    0.60    --  107.75 -82.00 107.06   52
 44  ω     61.00 110.00   0.50    0.60    --  107.75-125.00 -60.00   98
 45  ω     60.00 124.00   0.50    0.60    --  107.75-141.00  21.93  128
 46  ω     86.00 177.00   0.50    0.60    --  107.75  77.00-180.00  182
 47  ω    110.00 136.00   0.50    0.60    --  107.75  58.00 -49.11   52
 48  ω    141.00 167.00   0.50    0.60    --  107.75  58.00 -49.11   52
 49  ω    141.00 167.00   0.50    0.60    --  107.75 125.00 -30.00   52
 50  ω     46.00 105.00   0.50    0.60    --  107.75 -83.00   2.19  118
 51  ω     78.00 104.00   0.50    0.60    --  107.75-103.00 -59.40   52
 52  ω     46.00  72.00   0.50    0.60    --  107.75-103.00 -59.40   52
 53  ω     90.00 115.00   0.50    0.60    --  107.75-130.00-150.69   50
 54  ω     86.00 116.00   0.50    0.60    --  107.75  77.00  60.00   60
 55  ω     57.00  83.00   0.50    0.60    --  107.75-125.00  60.00   52
 56  ω     50.00  77.00   0.50    0.60    --  107.75-125.00 -30.00   54
 57  ω     68.00 121.00   0.50    0.60    --  107.75 -85.00 -40.20  106
 58  ω    137.00 177.00   0.50    0.60    --  107.75 125.00 150.00   80
 59  ω     55.00  84.00   0.50    0.60    --  107.75 -95.00-120.00   58
 60  ω     37.00  69.00   0.50    0.60    --  107.75 -61.00-120.00   64
 61  ω     98.00 157.00   0.50    0.60    --  107.75  30.00  30.00  118
 62  ω    128.00 154.00   0.50    0.60    --  107.75  15.00-150.00   52
 63  ω     74.00 105.00   0.50    0.60    --  107.75-110.00 -52.94   62
 64  ω     54.00  80.00   0.50    0.60    --  107.75 -77.00 -90.00   52
 65  ω     36.00  70.00   0.50    0.60    --  107.75 -77.00 -60.00   68
 66  ω     56.00  82.00   0.50    0.60    --  107.75 -77.00  60.00   52
 67  ω     74.00  99.00   0.50    0.60    --  107.75 -77.00 120.00   50
 68  ω     42.00  84.00   0.50    0.60    --  107.75-130.00-150.69   84
 69  ω    127.00 172.00   0.50    0.60    --  107.75  45.00 -90.00   90
 70  ω    109.00 135.00   0.50    0.60    --  107.75  45.00 150.00   52
 71  ω    135.00 168.00   0.50    0.60    --  107.75  30.00-150.00   66
 72  ω    134.00 178.00   0.50    0.60    --  107.75  30.00 -60.00   88
 73  ω    123.00 149.00   0.50    0.60    --  107.75  61.00  30.00   52
 74  ω    153.00 178.00   0.50    0.60    --  107.75  61.00  30.00   50
 75  ω     87.00 152.00   0.50    0.60    --  107.75  77.00 -60.00  130
 76  ω     82.00 108.00   0.50    0.60    --  107.75 -79.00-142.37   52
 77  ω     92.00 123.00   0.50    0.60    --  107.75 -87.00  16.05   62
 78  ω     38.00  70.00   0.50    0.60    --  107.75 -61.00  60.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0690235000
_diffrn_orient_matrix_UB_12      -0.1458301000
_diffrn_orient_matrix_UB_13      -0.0128501000
_diffrn_orient_matrix_UB_21      -0.0441053000
_diffrn_orient_matrix_UB_22      -0.0076798000
_diffrn_orient_matrix_UB_23      -0.0847211000
_diffrn_orient_matrix_UB_31      0.1484363000
_diffrn_orient_matrix_UB_32      -0.0208362000
_diffrn_orient_matrix_UB_33      -0.0174995000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7204
_reflns_number_total             7592
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.034
_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)+(0.0459P)²+0.6067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
  C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,
 H32B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B),
 C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.25483(7) 0.31460(6) 0.23138(3) 0.02328(14) Uani 1 1 d . . . . .
F2 F 0.25337(7) 0.81830(6) 0.27576(3) 0.02450(14) Uani 1 1 d . . . . .
O1 O 0.20970(8) 0.25833(7) 0.34889(4) 0.02076(15) Uani 1 1 d . . . . .
O2 O 0.31116(8) 0.72704(7) 0.15688(4) 0.02276(16) Uani 1 1 d . . . . .
N1 N 0.34393(9) 0.46932(8) 0.35361(5) 0.01825(17) Uani 1 1 d . . . . .
N2 N 0.26377(9) 0.46393(8) 0.41581(5) 0.01959(17) Uani 1 1 d . . . . .
N3 N 0.17078(9) 0.86900(8) 0.15689(5) 0.01911(17) Uani 1 1 d . . . . .
N4 N 0.25858(10) 0.87446(8) 0.09757(5) 0.02060(18) Uani 1 1 d . . . . .
C1 C 0.19324(11) 0.34334(9) 0.40705(6) 0.01854(19) Uani 1 1 d . . . . .
C2 C 0.09497(11) 0.29893(10) 0.46128(6) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.01924(11) 0.16954(10) 0.45117(6) 0.0222(2) Uani 1 1 d . . . . .
H3 H 0.030108 0.109150 0.408780 0.027 Uiso 1 1 calc R U . . .
C4 C -0.07230(12) 0.12905(11) 0.50330(7) 0.0258(2) Uani 1 1 d . . . . .
H4 H -0.124722 0.040998 0.496142 0.031 Uiso 1 1 calc R U . . .
C5 C -0.08734(12) 0.21683(12) 0.56575(7) 0.0276(2) Uani 1 1 d . . . . .
H5 H -0.149043 0.188754 0.601571 0.033 Uiso 1 1 calc R U . . .
C6 C -0.01180(13) 0.34608(12) 0.57576(6) 0.0274(2) Uani 1 1 d . . . . .
H6 H -0.022755 0.406218 0.618267 0.033 Uiso 1 1 calc R U . . .
C7 C 0.07919(12) 0.38737(10) 0.52408(6) 0.0231(2) Uani 1 1 d . . . . .
H7 H 0.130837 0.475601 0.531228 0.028 Uiso 1 1 calc R U . . .
C8 C 0.46650(11) 0.28081(9) 0.30732(6) 0.0190(2) Uani 1 1 d . . . . .
H8 H 0.532308 0.325582 0.274434 0.023 Uiso 1 1 calc R U . . .
C9 C 0.55418(12) 0.31133(10) 0.38668(6) 0.0225(2) Uani 1 1 d . . . . .
H9A H 0.585188 0.405081 0.407179 0.027 Uiso 1 1 calc R U . . .
H9B H 0.490006 0.270830 0.420934 0.027 Uiso 1 1 calc R U . . .
C10 C 0.69045(12) 0.26347(11) 0.38535(7) 0.0266(2) Uani 1 1 d . . . . .
H10A H 0.759797 0.310549 0.355543 0.032 Uiso 1 1 calc R U . . .
H10B H 0.740757 0.280788 0.437803 0.032 Uiso 1 1 calc R U . . .
C11 C 0.64850(13) 0.11980(11) 0.35032(7) 0.0311(3) Uani 1 1 d . . . . .
H11A H 0.738974 0.092735 0.346783 0.037 Uiso 1 1 calc R U . . .
H11B H 0.589108 0.072127 0.383611 0.037 Uiso 1 1 calc R U . . .
C12 C 0.56070(13) 0.08699(11) 0.27135(7) 0.0291(2) Uani 1 1 d . . . . .
H12A H 0.528904 -0.007029 0.251869 0.035 Uiso 1 1 calc R U . . .
H12B H 0.624255 0.125906 0.236356 0.035 Uiso 1 1 calc R U . . .
C13 C 0.42574(11) 0.13591(10) 0.27320(6) 0.0221(2) Uani 1 1 d . . . . .
H13A H 0.357144 0.089614 0.303633 0.026 Uiso 1 1 calc R U . . .
H13B H 0.374318 0.117371 0.220889 0.026 Uiso 1 1 calc R U . . .
C14 C 0.42025(11) 0.57901(10) 0.34461(6) 0.0191(2) Uani 1 1 d . . . . .
C15 C 0.43754(11) 0.70248(10) 0.40000(6) 0.0211(2) Uani 1 1 d . . . . .
H15A H 0.384397 0.685862 0.443526 0.025 Uiso 1 1 calc R U . . .
H15B H 0.395650 0.759260 0.375239 0.025 Uiso 1 1 calc R U . . .
C16 C 0.60217(12) 0.76709(11) 0.42784(6) 0.0264(2) Uani 1 1 d . . . . .
H16A H 0.615541 0.851947 0.461511 0.032 Uiso 1 1 calc R U . . .
H16B H 0.640464 0.714356 0.457688 0.032 Uiso 1 1 calc R U . . .
C17 C 0.68908(13) 0.78368(11) 0.36147(7) 0.0306(2) Uani 1 1 d . . . . .
H17A H 0.795007 0.822171 0.381030 0.037 Uiso 1 1 calc R U . . .
H17B H 0.657078 0.842987 0.334482 0.037 Uiso 1 1 calc R U . . .
C18 C 0.66695(12) 0.65586(11) 0.30597(7) 0.0262(2) Uani 1 1 d . . . . .
H18A H 0.709721 0.600136 0.331251 0.031 Uiso 1 1 calc R U . . .
H18B H 0.719261 0.670696 0.261938 0.031 Uiso 1 1 calc R U . . .
C19 C 0.50285(12) 0.58815(10) 0.27804(6) 0.0222(2) Uani 1 1 d . . . . .
H19A H 0.463278 0.636803 0.245686 0.027 Uiso 1 1 calc R U . . .
H19B H 0.490499 0.501256 0.247221 0.027 Uiso 1 1 calc R U . . .
C20 C 0.33126(11) 0.79259(10) 0.10312(6) 0.0202(2) Uani 1 1 d . . . . .
C21 C 0.43533(11) 0.76934(9) 0.05026(6) 0.0210(2) Uani 1 1 d . . . . .
C22 C 0.51540(12) 0.68375(10) 0.05864(6) 0.0245(2) Uani 1 1 d . . . . .
H22 H 0.505246 0.642033 0.099785 0.029 Uiso 1 1 calc R U . . .
C23 C 0.60993(13) 0.65954(11) 0.00687(7) 0.0280(2) Uani 1 1 d . . . . .
H23 H 0.664758 0.601575 0.012845 0.034 Uiso 1 1 calc R U . . .
C24 C 0.62466(13) 0.71967(11) -0.05358(7) 0.0295(2) Uani 1 1 d . . . . .
H24 H 0.688305 0.701948 -0.089353 0.035 Uiso 1 1 calc R U . . .
C25 C 0.54585(13) 0.80610(11) -0.06165(7) 0.0294(2) Uani 1 1 d . . . . .
H25 H 0.557086 0.848261 -0.102583 0.035 Uiso 1 1 calc R U . . .
C26 C 0.45144(12) 0.83082(10) -0.01045(6) 0.0246(2) Uani 1 1 d . . . . .
H26 H 0.397494 0.889436 -0.016385 0.030 Uiso 1 1 calc R U . . .
C27 C 0.05050(11) 0.64058(10) 0.19020(6) 0.0215(2) Uani 1 1 d . . . . .
H27 H -0.022446 0.669604 0.220471 0.026 Uiso 1 1 calc R U . . .
C28 C 0.08909(12) 0.53395(10) 0.22271(6) 0.0237(2) Uani 1 1 d . . . . .
H28A H 0.163960 0.505690 0.194744 0.028 Uiso 1 1 calc R U . . .
H28B H 0.132492 0.568633 0.276619 0.028 Uiso 1 1 calc R U . . .
C29 C -0.04531(13) 0.41864(11) 0.21713(7) 0.0312(3) Uani 1 1 d . . . . .
H29A H -0.014735 0.351250 0.236723 0.037 Uiso 1 1 calc R U . . .
H29B H -0.116807 0.444678 0.248803 0.037 Uiso 1 1 calc R U . . .
C30 C -0.11807(16) 0.36549(12) 0.13525(9) 0.0404(3) Uani 1 1 d . . . . .
H30A H -0.208139 0.294403 0.133254 0.049 Uiso 1 1 calc R U . . .
H30B H -0.050152 0.330792 0.104809 0.049 Uiso 1 1 calc R U . . .
C31 C -0.15847(15) 0.46903(12) 0.10098(8) 0.0399(3) Uani 1 1 d . . . . .
H31A H -0.235593 0.496180 0.127473 0.048 Uiso 1 1 calc R U . . .
H31B H -0.198995 0.433162 0.046773 0.048 Uiso 1 1 calc R U . . .
C32 C -0.02426(14) 0.58555(11) 0.10783(7) 0.0310(3) Uani 1 1 d . . . . .
H32A H -0.055522 0.652667 0.088283 0.037 Uiso 1 1 calc R U . . .
H32B H 0.047588 0.560378 0.076084 0.037 Uiso 1 1 calc R U . . .
C33 C 0.09065(11) 0.94553(9) 0.16808(5) 0.0195(2) Uani 1 1 d . . . . .
C34 C 0.07875(12) 1.03666(10) 0.11893(6) 0.0214(2) Uani 1 1 d . . . . .
H34A H 0.139543 1.027563 0.077451 0.026 Uiso 1 1 calc R U . . .
H34B H 0.115360 1.125777 0.149319 0.026 Uiso 1 1 calc R U . . .
C35 C -0.08322(12) 1.00745(10) 0.08541(6) 0.0234(2) Uani 1 1 d . . . . .
H35A H -0.092812 1.072121 0.056337 0.028 Uiso 1 1 calc R U . . .
H35B H -0.115386 0.922361 0.049970 0.028 Uiso 1 1 calc R U . . .
C36 C -0.18179(12) 1.00874(11) 0.14761(7) 0.0273(2) Uani 1 1 d . . . . .
H36A H -0.285701 0.984921 0.124262 0.033 Uiso 1 1 calc R U . . .
H36B H -0.156537 1.096349 0.179819 0.033 Uiso 1 1 calc R U . . .
C37 C -0.16429(12) 0.91568(11) 0.19690(6) 0.0262(2) Uani 1 1 d . . . . .
H37A H -0.200123 0.826991 0.165857 0.031 Uiso 1 1 calc R U . . .
H37B H -0.225142 0.922550 0.238536 0.031 Uiso 1 1 calc R U . . .
C38 C -0.00266(12) 0.94371(10) 0.23082(6) 0.0229(2) Uani 1 1 d . . . . .
H38A H 0.029907 1.027519 0.267542 0.027 Uiso 1 1 calc R U . . .
H38B H 0.007406 0.876876 0.258035 0.027 Uiso 1 1 calc R U . . .
B1 B 0.32120(13) 0.32616(11) 0.30469(6) 0.0192(2) Uani 1 1 d . . . . .
B2 B 0.19357(13) 0.76064(11) 0.20026(6) 0.0204(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3942(13) . ?
F2 B2 1.3968(13) . ?
O1 C1 1.3228(12) . ?
O1 B1 1.5071(13) . ?
O2 C20 1.3221(12) . ?
O2 B2 1.5038(13) . ?
N1 N2 1.4112(11) . ?
N1 C14 1.2887(13) . ?
N1 B1 1.6148(13) . ?
N2 C1 1.3004(13) . ?
N3 N4 1.4125(12) . ?
N3 C33 1.2883(14) . ?
N3 B2 1.6140(14) . ?
N4 C20 1.2992(14) . ?
C1 C2 1.4717(14) . ?
C2 C3 1.3939(15) . ?
C2 C7 1.3997(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3911(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3885(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3924(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3842(15) . ?
C7 H7 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.5348(14) . ?
C8 C13 1.5400(14) . ?
C8 B1 1.5978(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5317(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5301(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5267(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5268(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.4969(14) . ?
C14 C19 1.4950(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5362(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5241(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5266(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5367(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.4686(14) . ?
C21 C22 1.3951(15) . ?
C21 C26 1.4014(15) . ?
C22 H22 0.9500 . ?
C22 C23 1.3884(16) . ?
C23 H23 0.9500 . ?
C23 C24 1.3878(17) . ?
C24 H24 0.9500 . ?
C24 C25 1.3932(18) . ?
C25 H25 0.9500 . ?
C25 C26 1.3818(16) . ?
C26 H26 0.9500 . ?
C27 H27 1.0000 . ?
C27 C28 1.5385(14) . ?
C27 C32 1.5355(15) . ?
C27 B2 1.5993(15) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.5287(15) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.5208(19) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.5314(18) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.5322(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.4946(14) . ?
C33 C38 1.4961(14) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.5380(15) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.5221(15) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.5264(15) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.5390(15) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 108.72(8) . . ?
C20 O2 B2 108.81(8) . . ?
N2 N1 B1 109.66(7) . . ?
C14 N1 N2 119.28(8) . . ?
C14 N1 B1 131.06(8) . . ?
C1 N2 N1 104.74(8) . . ?
N4 N3 B2 109.49(8) . . ?
C33 N3 N4 119.14(8) . . ?
C33 N3 B2 131.37(9) . . ?
C20 N4 N3 104.84(8) . . ?
O1 C1 C2 118.95(9) . . ?
N2 C1 O1 120.03(9) . . ?
N2 C1 C2 121.02(9) . . ?
C3 C2 C1 120.59(9) . . ?
C3 C2 C7 119.82(10) . . ?
C7 C2 C1 119.59(9) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.85(10) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.26(10) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.86(10) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.31(10) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.90(10) . . ?
C6 C7 H7 120.1 . . ?
C9 C8 H8 107.7 . . ?
C9 C8 C13 109.46(8) . . ?
C9 C8 B1 114.67(8) . . ?
C13 C8 H8 107.7 . . ?
C13 C8 B1 109.48(8) . . ?
B1 C8 H8 107.7 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.98(9) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.08(9) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C10 111.38(10) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C11 C12 C13 111.14(9) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C8 C13 H13A 109.2 . . ?
C8 C13 H13B 109.2 . . ?
C12 C13 C8 112.21(9) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N1 C14 C15 123.36(9) . . ?
N1 C14 C19 120.55(9) . . ?
C19 C14 C15 116.05(9) . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
C14 C15 C16 108.65(8) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 C15 111.22(9) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C16 C17 C18 111.45(9) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C17 C18 C19 111.24(9) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C14 C19 C18 109.67(8) . . ?
C14 C19 H19A 109.7 . . ?
C14 C19 H19B 109.7 . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
O2 C20 C21 118.51(9) . . ?
N4 C20 O2 119.93(9) . . ?
N4 C20 C21 121.56(9) . . ?
C22 C21 C20 120.57(9) . . ?
C22 C21 C26 119.60(10) . . ?
C26 C21 C20 119.80(10) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.01(10) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.27(11) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.81(11) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.36(11) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 119.94(11) . . ?
C25 C26 H26 120.0 . . ?
C28 C27 H27 107.6 . . ?
C28 C27 B2 110.20(8) . . ?
C32 C27 H27 107.6 . . ?
C32 C27 C28 109.36(9) . . ?
C32 C27 B2 114.11(9) . . ?
B2 C27 H27 107.6 . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 C27 112.32(9) . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C30 C29 C28 110.62(10) . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C29 C30 H30A 109.4 . . ?
C29 C30 H30B 109.4 . . ?
C29 C30 C31 111.31(10) . . ?
H30A C30 H30B 108.0 . . ?
C31 C30 H30A 109.4 . . ?
C31 C30 H30B 109.4 . . ?
C30 C31 H31A 109.4 . . ?
C30 C31 H31B 109.4 . . ?
C30 C31 C32 111.36(11) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C27 C32 H32A 109.2 . . ?
C27 C32 H32B 109.2 . . ?
C31 C32 C27 112.09(10) . . ?
C31 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
N3 C33 C34 123.54(9) . . ?
N3 C33 C38 120.78(9) . . ?
C34 C33 C38 115.63(9) . . ?
C33 C34 H34A 109.8 . . ?
C33 C34 H34B 109.8 . . ?
C33 C34 C35 109.16(8) . . ?
H34A C34 H34B 108.3 . . ?
C35 C34 H34A 109.8 . . ?
C35 C34 H34B 109.8 . . ?
C34 C35 H35A 109.4 . . ?
C34 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 C34 111.17(9) . . ?
C36 C35 H35A 109.4 . . ?
C36 C35 H35B 109.4 . . ?
C35 C36 H36A 109.4 . . ?
C35 C36 H36B 109.4 . . ?
C35 C36 C37 111.34(9) . . ?
H36A C36 H36B 108.0 . . ?
C37 C36 H36A 109.4 . . ?
C37 C36 H36B 109.4 . . ?
C36 C37 H37A 109.3 . . ?
C36 C37 H37B 109.3 . . ?
C36 C37 C38 111.43(9) . . ?
H37A C37 H37B 108.0 . . ?
C38 C37 H37A 109.3 . . ?
C38 C37 H37B 109.3 . . ?
C33 C38 C37 109.05(8) . . ?
C33 C38 H38A 109.9 . . ?
C33 C38 H38B 109.9 . . ?
C37 C38 H38A 109.9 . . ?
C37 C38 H38B 109.9 . . ?
H38A C38 H38B 108.3 . . ?
F1 B1 O1 109.64(8) . . ?
F1 B1 N1 109.22(8) . . ?
F1 B1 C8 113.79(8) . . ?
O1 B1 N1 96.58(7) . . ?
O1 B1 C8 112.19(8) . . ?
C8 B1 N1 114.10(8) . . ?
F2 B2 O2 109.47(8) . . ?
F2 B2 N3 109.15(8) . . ?
F2 B2 C27 114.10(9) . . ?
O2 B2 N3 96.71(7) . . ?
O2 B2 C27 111.98(9) . . ?
C27 B2 N3 114.05(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
O1 C1 C2 C3 -0.62(14) . . . . ?
O1 C1 C2 C7 178.49(9) . . . . ?
O2 C20 C21 C22 -2.56(14) . . . . ?
O2 C20 C21 C26 175.63(9) . . . . ?
N1 N2 C1 O1 0.84(12) . . . . ?
N1 N2 C1 C2 -179.44(8) . . . . ?
N1 C14 C15 C16 121.66(11) . . . . ?
N1 C14 C19 C18 -122.60(10) . . . . ?
N2 N1 C14 C15 4.39(14) . . . . ?
N2 N1 C14 C19 -178.23(8) . . . . ?
N2 N1 B1 F1 118.58(8) . . . . ?
N2 N1 B1 O1 5.09(9) . . . . ?
N2 N1 B1 C8 -112.81(9) . . . . ?
N2 C1 C2 C3 179.65(9) . . . . ?
N2 C1 C2 C7 -1.24(15) . . . . ?
N3 N4 C20 O2 0.19(12) . . . . ?
N3 N4 C20 C21 179.52(8) . . . . ?
N3 C33 C34 C35 121.29(10) . . . . ?
N3 C33 C38 C37 -121.77(10) . . . . ?
N4 N3 C33 C34 3.28(14) . . . . ?
N4 N3 C33 C38 -179.35(8) . . . . ?
N4 N3 B2 F2 117.73(9) . . . . ?
N4 N3 B2 O2 4.39(9) . . . . ?
N4 N3 B2 C27 -113.34(9) . . . . ?
N4 C20 C21 C22 178.11(10) . . . . ?
N4 C20 C21 C26 -3.71(15) . . . . ?
C1 O1 B1 F1 -117.61(9) . . . . ?
C1 O1 B1 N1 -4.46(9) . . . . ?
C1 O1 B1 C8 114.94(9) . . . . ?
C1 C2 C3 C4 179.48(9) . . . . ?
C1 C2 C7 C6 -179.29(9) . . . . ?
C2 C3 C4 C5 -0.65(16) . . . . ?
C3 C2 C7 C6 -0.17(15) . . . . ?
C3 C4 C5 C6 0.73(16) . . . . ?
C4 C5 C6 C7 -0.53(17) . . . . ?
C5 C6 C7 C2 0.25(16) . . . . ?
C7 C2 C3 C4 0.37(15) . . . . ?
C8 C9 C10 C11 -56.05(12) . . . . ?
C9 C8 C13 C12 -55.57(12) . . . . ?
C9 C8 B1 F1 171.20(8) . . . . ?
C9 C8 B1 O1 -63.60(11) . . . . ?
C9 C8 B1 N1 44.94(12) . . . . ?
C9 C10 C11 C12 54.99(13) . . . . ?
C10 C11 C12 C13 -54.86(13) . . . . ?
C11 C12 C13 C8 55.79(13) . . . . ?
C13 C8 C9 C10 55.61(11) . . . . ?
C13 C8 B1 F1 -65.34(11) . . . . ?
C13 C8 B1 O1 59.86(11) . . . . ?
C13 C8 B1 N1 168.40(8) . . . . ?
C14 N1 N2 C1 176.60(9) . . . . ?
C14 N1 B1 F1 -62.03(13) . . . . ?
C14 N1 B1 O1 -175.51(10) . . . . ?
C14 N1 B1 C8 66.58(13) . . . . ?
C14 C15 C16 C17 54.79(12) . . . . ?
C15 C14 C19 C18 54.97(12) . . . . ?
C15 C16 C17 C18 -56.69(13) . . . . ?
C16 C17 C18 C19 55.26(13) . . . . ?
C17 C18 C19 C14 -52.54(12) . . . . ?
C19 C14 C15 C16 -55.83(11) . . . . ?
C20 O2 B2 F2 -117.22(9) . . . . ?
C20 O2 B2 N3 -4.13(9) . . . . ?
C20 O2 B2 C27 115.21(9) . . . . ?
C20 C21 C22 C23 177.95(10) . . . . ?
C20 C21 C26 C25 -177.98(10) . . . . ?
C21 C22 C23 C24 -0.34(17) . . . . ?
C22 C21 C26 C25 0.22(16) . . . . ?
C22 C23 C24 C25 0.95(17) . . . . ?
C23 C24 C25 C26 -0.97(17) . . . . ?
C24 C25 C26 C21 0.39(17) . . . . ?
C26 C21 C22 C23 -0.24(16) . . . . ?
C27 C28 C29 C30 56.91(13) . . . . ?
C28 C27 C32 C31 54.77(13) . . . . ?
C28 C27 B2 F2 -62.34(12) . . . . ?
C28 C27 B2 O2 62.72(11) . . . . ?
C28 C27 B2 N3 171.27(8) . . . . ?
C28 C29 C30 C31 -55.60(15) . . . . ?
C29 C30 C31 C32 55.05(17) . . . . ?
C30 C31 C32 C27 -55.16(16) . . . . ?
C32 C27 C28 C29 -55.89(12) . . . . ?
C32 C27 B2 F2 174.18(9) . . . . ?
C32 C27 B2 O2 -60.76(12) . . . . ?
C32 C27 B2 N3 47.79(12) . . . . ?
C33 N3 N4 C20 176.62(9) . . . . ?
C33 N3 B2 F2 -61.94(14) . . . . ?
C33 N3 B2 O2 -175.28(10) . . . . ?
C33 N3 B2 C27 67.00(14) . . . . ?
C33 C34 C35 C36 54.35(11) . . . . ?
C34 C33 C38 C37 55.80(11) . . . . ?
C34 C35 C36 C37 -55.88(12) . . . . ?
C35 C36 C37 C38 55.66(12) . . . . ?
C36 C37 C38 C33 -53.65(12) . . . . ?
C38 C33 C34 C35 -56.20(11) . . . . ?
B1 O1 C1 N2 2.83(12) . . . . ?
B1 O1 C1 C2 -176.90(8) . . . . ?
B1 N1 N2 C1 -3.92(10) . . . . ?
B1 N1 C14 C15 -174.95(9) . . . . ?
B1 N1 C14 C19 2.43(16) . . . . ?
B1 C8 C9 C10 179.08(9) . . . . ?
B1 C8 C13 C12 177.95(9) . . . . ?
B2 O2 C20 N4 3.00(12) . . . . ?
B2 O2 C20 C21 -176.35(9) . . . . ?
B2 N3 N4 C20 -3.09(10) . . . . ?
B2 N3 C33 C34 -177.08(9) . . . . ?
B2 N3 C33 C38 0.29(16) . . . . ?
B2 C27 C28 C29 177.91(9) . . . . ?
B2 C27 C32 C31 178.70(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.585
####################################################################### 
# 
# 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_km1802-3
_database_code_depnum_ccdc_archive 'CCDC 2336547'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_km1802-3            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.70 eA-3  
RESPONSE: Largest peaks of the residual electron density are resulted
from presence of disordered part of the molecule, that could not be
modeled due to low occupancy of the second component.
;
_vrf_PLAT918_km1802-3            
;
PROBLEM: Reflection(s) with I(obs) much Smaller I(calc) .          1 Check 
RESPONSE: The multidomain crystal was refined as a two-component twin.
;
# end Validation Reply Form
_audit_creation_date             2024-02-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H21NO2
_chemical_oxdiff_usercomment     KM1802.3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.0689(2)
_cell_length_b                   11.9115(2)
_cell_length_c                   9.37870(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.217(2)
_cell_angle_gamma                90
_cell_volume                     1317.74(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22366
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.3190
_cell_measurement_theta_min      3.7580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 0 0.0457
2 1 0 0.0295
-1 -1 2 0.0959
-1 0 0 0.0247
1 0 0 0.0162
-2 1 0 0.0434
2 -1 0 0.0332
-1 1 -2 0.1300
0 -1 0 0.0650
-1 -2 -1 0.0965

_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.041
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9995 -0.9960 0.0008 -0.0712 -0.2701 0.0822
1.9995 0.9960 -0.0008 0.0712 0.2701 -0.0822
-0.9989 -0.9979 2.0003 -0.0423 -0.1977 -0.2953
-0.9991 0.0015 0.0001 0.0262 -0.1180 0.0492
0.9991 -0.0015 -0.0001 -0.0262 0.1180 -0.0492
-1.9968 1.0019 -0.0003 0.1760 -0.2019 0.1144
1.9968 -1.0019 0.0003 -0.1760 0.2019 -0.1144
-0.9993 1.0009 -2.0000 0.0947 -0.0383 0.3936
-0.0014 -0.9989 0.0005 -0.1236 -0.0341 -0.0161
-1.0026 -1.9961 -0.9986 -0.2485 -0.1634 0.1812

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.810
_diffrn_reflns_theta_min         3.747
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -46.00   0.50    1.00    --  -44.25 119.00-122.00   50
  2  ω    -85.00 -60.00   0.50    1.00    --  -44.25 157.00  33.00   50
  3  ω   -113.00 -53.00   0.50    1.00    --  -44.25-157.00  -2.00  120
  4  ω     77.00 115.00   0.50    1.00    --   44.25-157.00  -2.00   76
  5  ω     78.00 106.00   0.50    1.00    --   44.25 157.00  33.00   56
  6  ω     41.00  90.00   0.50    1.00    --   44.25-119.00 153.00   98
  7  ω   -122.00 -97.00   0.50    4.00    --  -96.00-157.00  -2.00   50
  8  ω    -79.00 -54.00   0.50    4.00    --  -96.00 119.00-122.00   50
  9  ω   -146.00-121.00   0.50    4.00    --  -96.00-119.00 153.00   50
 10  ω     78.00 109.00   0.50    4.00    --  117.50-119.00 153.00   62
 11  ω    114.00 139.00   0.50    4.00    --  117.50 119.00-122.00   50
 12  ω     92.00 117.00   0.50    4.00    --  117.50-157.00  -2.00   50
 13  ω    117.00 142.00   0.50    4.00    --  117.50 157.00  33.00   50
 14  ω    -27.00   7.00   0.50    1.00    --  -44.25  19.00 150.00   68
 15  ω    -13.00  35.00   0.50    1.00    --  -44.25  19.00-120.00   96
 16  ω     -9.00  34.00   0.50    1.00    --  -44.25  19.00  90.00   86
 17  ω     -4.00  25.00   0.50    1.00    --  -44.25  19.00-150.00   58
 18  ω    -27.00  34.00   0.50    1.00    --  -44.25  19.00-180.00  122
 19  ω    -28.00  24.00   0.50    1.00    --   44.25 -19.00 -30.00  104
 20  ω    -21.00  41.00   0.50    1.00    --   44.25 -38.00-120.00  124
 21  ω    -49.00 -21.00   0.50    4.00    --  -96.00  45.00 120.00   56
 22  ω    -51.00 -26.00   0.50    4.00    --  -96.00  45.00  90.00   50
 23  ω    -50.00 -21.00   0.50    4.00    --  -96.00  45.00  30.00   58
 24  ω    -51.00 -24.00   0.50    4.00    --  -96.00  45.00 -90.00   54
 25  ω     45.00  70.00   0.50    4.00    --  117.50 -61.00 -90.00   50
 26  ω     49.00 105.00   0.50    4.00    --  117.50 -95.00 150.00  112
 27  ω    133.00 159.00   0.50    4.00    --  117.50 125.00 -60.00   52
 28  ω     74.00 103.00   0.50    4.00    --  117.50-125.00   0.00   58
 29  ω     46.00  71.00   0.50    4.00    --  117.50 -61.00  90.00   50
 30  ω     51.00 107.00   0.50    4.00    --  117.50-106.00  94.43  112
 31  ω     45.00  70.00   0.50    4.00    --  117.50 -61.00 -60.00   50
 32  ω     64.00  90.00   0.50    4.00    --  117.50-125.00-120.00   52
 33  ω    121.00 175.00   0.50    4.00    --  117.50  45.00 150.00  108
 34  ω     46.00  71.00   0.50    4.00    --  117.50 -61.00  60.00   50
 35  ω     89.00 123.00   0.50    4.00    --  117.50  15.00-180.00   68
 36  ω     54.00  80.00   0.50    4.00    --  117.50 -77.00-120.00   52
 37  ω     57.00  83.00   0.50    4.00    --  117.50-112.00  16.63   52
 38  ω     84.00 109.00   0.50    4.00    --  117.50-112.00  16.63   50
 39  ω     76.00 105.00   0.50    4.00    --  117.50 -95.00 -90.00   58
 40  ω     49.00  74.00   0.50    4.00    --  117.50-125.00-150.00   50
 41  ω     98.00 124.00   0.50    4.00    --  117.50 125.00 -60.00   52
 42  ω     99.00 150.00   0.50    4.00    --  117.50 -88.00-139.13  102
 43  ω    105.00 177.00   0.50    4.00    --  117.50  61.00 -30.00  144
 44  ω     86.00 111.00   0.50    4.00    --  117.50-125.00 -90.00   50
 45  ω     70.00  96.00   0.50    4.00    --  117.50 -95.00   0.00   52
 46  ω     93.00 163.00   0.50    4.00    --  117.50  77.00  60.00  140
 47  ω    114.00 146.00   0.50    4.00    --  117.50 -81.00 127.20   64
 48  ω    107.00 138.00   0.50    4.00    --  117.50  30.00 -90.00   62
 49  ω     72.00  98.00   0.50    4.00    --  117.50 -81.00 127.20   52
 50  ω     45.00  77.00   0.50    4.00    --  117.50 -77.00 -90.00   64
 51  ω     45.00  70.00   0.50    4.00    --  117.50 -61.00-150.00   50
 52  ω    101.00 158.00   0.50    4.00    --  117.50  30.00 120.00  114
 53  ω     46.00  93.00   0.50    4.00    --  117.50 -77.00  60.00   94
 54  ω    109.00 159.00   0.50    4.00    --  117.50  15.00 -60.00  100
 55  ω    101.00 133.00   0.50    4.00    --  117.50  77.00   0.00   64
 56  ω    105.00 131.00   0.50    4.00    --  117.50  45.00-150.00   52
 57  ω    135.00 178.00   0.50    4.00    --  117.50  45.00-150.00   86
 58  ω     47.00  80.00   0.50    4.00    --  117.50-125.00  90.00   66
 59  ω     85.00 111.00   0.50    4.00    --  117.50-125.00  90.00   52
 60  ω     51.00  81.00   0.50    4.00    --  117.50-125.00 -90.00   60
 61  ω     66.00 107.00   0.50    4.00    --  117.50-125.00  30.00   82
 62  ω    107.00 132.00   0.50    4.00    --  117.50  45.00  60.00   50
 63  ω     46.00  74.00   0.50    4.00    --  117.50 -95.00-150.00   56
 64  ω     80.00 105.00   0.50    4.00    --  117.50 -95.00-150.00   50
 65  ω     48.00  73.00   0.50    4.00    --  117.50 -95.00 -90.00   50
 66  ω    150.00 176.00   0.50    4.00    --  117.50   0.00 -90.00   52
 67  ω     46.00  73.00   0.50    4.00    --  117.50 -95.00 120.00   54
 68  ω    121.00 178.00   0.50    4.00    --  117.50  30.00-120.00  114
 69  ω     73.00  99.00   0.50    4.00    --  117.50 -77.00   0.00   52
 70  ω     81.00 108.00   0.50    4.00    --  117.50-125.00-150.00   54
 71  ω     48.00 109.00   0.50    4.00    --  117.50-125.00  60.00  122
 72  ω     79.00 113.00   0.50    4.00    --  117.50   0.00 -90.00   68
 73  ω    109.00 134.00   0.50    4.00    --  117.50  77.00 -60.00   50
 74  ω    143.00 178.00   0.50    4.00    --  117.50  77.00 -60.00   70
 75  ω    108.00 134.00   0.50    4.00    --  117.50  77.00 -30.00   52
 76  ω    124.00 149.00   0.50    4.00    --  117.50 -87.00  44.77   50
 77  ω     50.00  98.00   0.50    4.00    --  117.50 -87.00  44.77   96
 78  ω     45.00  75.00   0.50    4.00    --  117.50   0.00 -90.00   60
 79  ω     66.00 105.00   0.50    4.00    --  117.50 -95.00-180.00   78
 80  ω     71.00 102.00   0.50    4.00    --  117.50 -95.00 -60.00   62
 81  ω     73.00  98.00   0.50    4.00    --  117.50-125.00 -60.00   50
 82  ω     95.00 160.00   0.50    4.00    --  117.50 125.00 -30.00  130
 83  ω     86.00 111.00   0.50    4.00    --  117.50-125.00 120.00   50
 84  ω    126.00 167.00   0.50    4.00    --  117.50  61.00 -60.00   82
 85  ω    101.00 144.00   0.50    4.00    --  117.50  30.00 -60.00   86
 86  ω     98.00 155.00   0.50    4.00    --  117.50  30.00 -30.00  114
 87  ω    108.00 134.00   0.50    4.00    --  117.50  61.00  90.00   52
 88  ω     96.00 121.00   0.50    4.00    --  117.50  77.00  90.00   50
 89  ω     63.00  89.00   0.50    4.00    --  117.50 -80.00 145.72   52
 90  ω    120.00 146.00   0.50    4.00    --  117.50 -80.00 145.72   52
 91  ω    107.00 148.00   0.50    4.00    --  117.50 -87.00-162.66   82
 92  ω     45.00  70.00   0.50    4.00    --  117.50 -61.00 150.00   50
 93  ω     31.00  57.00   0.50    1.00    --   44.25  57.00  90.00   52
 94  ω     64.00  90.00   0.50    1.00    --   44.25-125.00 -90.00   52
 95  ω    120.00 164.00   0.50    4.00    --  117.50  45.00 120.00   88
 96  ω     63.00  89.00   0.50    4.00    --  117.50 -88.00 -18.64   52
 97  ω     51.00  77.00   0.50    4.00    --  117.50 -77.00 -60.00   52
 98  ω     48.00  74.00   0.50    4.00    --  117.50 -77.00   0.00   52
 99  ω     75.00 108.00   0.50    4.00    --  117.50-125.00-180.00   66
100  ω    132.00 158.00   0.50    4.00    --  117.50  30.00  30.00   52
101  ω     97.00 138.00   0.50    4.00    --  117.50  61.00-150.00   82
102  ω    153.00 178.00   0.50    4.00    --  117.50  61.00-150.00   50
103  ω    141.00 167.00   0.50    4.00    --  117.50 125.00 -30.00   52
104  ω    125.00 161.00   0.50    4.00    --  117.50 125.00-150.00   72
105  ω     55.00  81.00   0.50    4.00    --  117.50 -77.00-150.00   52
106  ω     78.00 104.00   0.50    4.00    --  117.50   6.00-118.85   52
107  ω    115.00 141.00   0.50    4.00    --  117.50   6.00-118.85   52
108  ω    124.00 168.00   0.50    4.00    --  117.50 125.00   0.00   88
109  ω    105.00 131.00   0.50    4.00    --  117.50 -88.00 -18.64   52
110  ω     63.00 114.00   0.50    4.00    --  117.50 -88.00-178.79  102
111  ω     98.00 124.00   0.50    4.00    --  117.50  45.00 -30.00   52
112  ω    142.00 168.00   0.50    4.00    --  117.50  45.00 -30.00   52
113  ω    117.00 155.00   0.50    4.00    --  117.50  30.00  90.00   76
114  ω    100.00 126.00   0.50    4.00    --  117.50  61.00  60.00   52
115  ω    140.00 166.00   0.50    4.00    --  117.50  61.00  60.00   52
116  ω     45.00  70.00   0.50    4.00    --  117.50 -61.00-120.00   50
117  ω     63.00 113.00   0.50    4.00    --  117.50 -86.00 -83.10  100
118  ω     53.00  79.00   0.50    4.00    --  117.50 -77.00-180.00   52
119  ω     55.00  81.00   0.50    4.00    --  117.50 -77.00 150.00   52
120  ω     47.00  73.00   0.50    4.00    --  117.50 -95.00 -90.00   52
121  ω     50.00  76.00   0.50    4.00    --  117.50 -95.00 120.00   52
122  ω     85.00 111.00   0.50    4.00    --  117.50-125.00 -30.00   52
123  ω     62.00  87.00   0.50    4.00    --  117.50-125.00 150.00   50
124  ω     83.00 109.00   0.50    4.00    --  117.50 -78.00 -95.21   52
125  ω    105.00 131.00   0.50    4.00    --  117.50 125.00-180.00   52
126  ω    139.00 165.00   0.50    4.00    --  117.50 125.00-120.00   52
127  ω     93.00 119.00   0.50    4.00    --  117.50  77.00 -90.00   52
128  ω    137.00 163.00   0.50    4.00    --  117.50  77.00   0.00   52
129  ω    101.00 127.00   0.50    4.00    --  117.50  77.00  30.00   52
130  ω     92.00 117.00   0.50    4.00    --  117.50  77.00 150.00   50
131  ω    114.00 140.00   0.50    4.00    --  117.50 -81.00 -44.91   52
132  ω     90.00 116.00   0.50    4.00    --  117.50 -88.00 124.00   52
133  ω     52.00 102.00   0.50    4.00    --  117.50-125.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0260323000
_diffrn_orient_matrix_UB_12      0.1237519000
_diffrn_orient_matrix_UB_13      0.0276074000
_diffrn_orient_matrix_UB_21      0.1181382000
_diffrn_orient_matrix_UB_22      0.0339628000
_diffrn_orient_matrix_UB_23      -0.0228950000
_diffrn_orient_matrix_UB_31      -0.0491966000
_diffrn_orient_matrix_UB_32      0.0160948000
_diffrn_orient_matrix_UB_33      -0.1641847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5413
_reflns_number_total             5581
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         5581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.037
_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)+(0.0802P)²+0.5963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1518
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4654(16)
 0.5346(16)
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:
 C9(H9), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.02668(11) 0.20018(11) 0.66526(12) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.26368(12) 0.71012(12) 0.82645(15) 0.0330(3) Uani 1 1 d . . . . .
H2 H 0.187(3) 0.695(3) 0.809(3) 0.068(10) Uiso 1 1 d . . . . .
N1 N 0.03398(12) 0.28011(12) 0.47490(15) 0.0189(3) Uani 1 1 d . . . . .
H1 H 0.023(2) 0.2797(19) 0.381(3) 0.025(5) Uiso 1 1 d . . . . .
C1 C 0.23935(14) 0.55292(14) 0.65899(19) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.19652(15) 0.54409(14) 0.50988(19) 0.0246(4) Uani 1 1 d . . . . .
H2A H 0.213779 0.600479 0.446314 0.030 Uiso 1 1 calc R U . . .
C3 C 0.12884(14) 0.45392(14) 0.45267(18) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.099976 0.449483 0.350410 0.027 Uiso 1 1 calc R U . . .
C4 C 0.10256(13) 0.36940(13) 0.54370(16) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.14624(14) 0.37638(15) 0.69328(17) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.130739 0.319093 0.756792 0.027 Uiso 1 1 calc R U . . .
C6 C 0.21302(15) 0.46847(16) 0.74875(18) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.241415 0.473664 0.851043 0.031 Uiso 1 1 calc R U . . .
C7 C -0.02585(13) 0.20472(13) 0.53394(17) 0.0194(3) Uani 1 1 d . . . . .
C8 C -0.09529(15) 0.12334(14) 0.42774(19) 0.0258(4) Uani 1 1 d . . . . .
H8A H -0.092135 0.048758 0.472534 0.039 Uiso 1 1 calc R U . . .
H8B H -0.064621 0.119441 0.339102 0.039 Uiso 1 1 calc R U . . .
H8C H -0.174171 0.149009 0.402664 0.039 Uiso 1 1 calc R U . . .
C9 C 0.31184(15) 0.65277(14) 0.72037(19) 0.0257(4) Uani 1 1 d . . . . .
H9 H 0.313719 0.705989 0.638458 0.031 Uiso 1 1 calc R U . . .
C10 C 0.43321(14) 0.62236(14) 0.79120(18) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.429972 0.577251 0.880153 0.027 Uiso 1 1 calc R U . . .
C11 C 0.50247(16) 0.72770(15) 0.8435(2) 0.0269(4) Uani 1 1 d . . . . .
H11A H 0.502735 0.777224 0.758762 0.032 Uiso 1 1 calc R U . . .
H11B H 0.465551 0.769022 0.912349 0.032 Uiso 1 1 calc R U . . .
C12 C 0.62425(17) 0.70138(17) 0.9182(2) 0.0347(4) Uani 1 1 d . . . . .
H12A H 0.666873 0.772426 0.941071 0.042 Uiso 1 1 calc R U . . .
H12B H 0.624865 0.661936 1.011325 0.042 Uiso 1 1 calc R U . . .
C13 C 0.68240(16) 0.62872(16) 0.8229(2) 0.0301(4) Uani 1 1 d . . . . .
H13A H 0.758588 0.607267 0.878523 0.036 Uiso 1 1 calc R U . . .
H13B H 0.692256 0.672591 0.736754 0.036 Uiso 1 1 calc R U . . .
C14 C 0.61445(16) 0.52282(16) 0.7718(2) 0.0320(4) Uani 1 1 d . . . . .
H14A H 0.651526 0.481329 0.703209 0.038 Uiso 1 1 calc R U . . .
H14B H 0.614063 0.473677 0.856815 0.038 Uiso 1 1 calc R U . . .
C15 C 0.49271(15) 0.55005(14) 0.6967(2) 0.0267(4) Uani 1 1 d . . . . .
H15A H 0.492776 0.589902 0.604042 0.032 Uiso 1 1 calc R U . . .
H15B H 0.450011 0.479157 0.672696 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.235(2) . ?
O2 H2 0.92(4) . ?
O2 C9 1.428(2) . ?
N1 H1 0.86(2) . ?
N1 C4 1.417(2) . ?
N1 C7 1.343(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.391(3) . ?
C1 C9 1.516(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(2) . ?
C4 C5 1.393(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.510(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 1.0000 . ?
C9 C10 1.519(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.530(2) . ?
C10 C15 1.521(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.519(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.525(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109(2) . . ?
C4 N1 H1 115.0(15) . . ?
C7 N1 H1 115.7(15) . . ?
C7 N1 C4 128.87(13) . . ?
C2 C1 C6 118.08(16) . . ?
C2 C1 C9 120.25(16) . . ?
C6 C1 C9 121.66(15) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.77(16) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.81(15) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 N1 116.64(14) . . ?
C5 C4 N1 124.32(14) . . ?
C5 C4 C3 119.03(15) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.22(15) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 122.07(15) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
O1 C7 N1 123.98(15) . . ?
O1 C7 C8 120.61(15) . . ?
N1 C7 C8 115.41(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C1 110.65(14) . . ?
O2 C9 H9 108.1 . . ?
O2 C9 C10 107.85(14) . . ?
C1 C9 H9 108.1 . . ?
C1 C9 C10 113.88(14) . . ?
C10 C9 H9 108.1 . . ?
C9 C10 H10 106.8 . . ?
C9 C10 C11 110.83(14) . . ?
C9 C10 C15 114.25(14) . . ?
C11 C10 H10 106.8 . . ?
C15 C10 H10 106.8 . . ?
C15 C10 C11 110.97(14) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.82(15) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.57(16) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.80(15) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C13 111.77(15) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C10 C15 C14 112.26(15) . . ?
C10 C15 H15A 109.2 . . ?
C10 C15 H15B 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.92(4) 2.00(4) 2.8803(19) 159(3) 2_556 yes
N1 H1 O1 0.86(2) 2.00(2) 2.8503(18) 169(2) 4_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 C11 -59.67(18) . . . . ?
O2 C9 C10 C15 174.07(14) . . . . ?
N1 C4 C5 C6 179.92(15) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C9 C10 C11 177.13(14) . . . . ?
C1 C9 C10 C15 50.9(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C9 O2 123.03(17) . . . . ?
C2 C1 C9 C10 -115.30(17) . . . . ?
C2 C3 C4 N1 -179.27(15) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 N1 C7 O1 -2.5(3) . . . . ?
C4 N1 C7 C8 177.01(14) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C9 O2 -56.5(2) . . . . ?
C6 C1 C9 C10 65.2(2) . . . . ?
C7 N1 C4 C3 -162.15(16) . . . . ?
C7 N1 C4 C5 19.2(3) . . . . ?
C9 C1 C2 C3 -179.12(15) . . . . ?
C9 C1 C6 C5 179.90(15) . . . . ?
C9 C10 C11 C12 178.78(15) . . . . ?
C9 C10 C15 C14 179.42(15) . . . . ?
C10 C11 C12 C13 53.5(2) . . . . ?
C11 C10 C15 C14 53.2(2) . . . . ?
C11 C12 C13 C14 -53.5(2) . . . . ?
C12 C13 C14 C15 54.0(2) . . . . ?
C13 C14 C15 C10 -54.2(2) . . . . ?
C15 C10 C11 C12 -53.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.351
_oxdiff_exptl_absorpt_empirical_full_min 0.514
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4654(16) 23969 8706 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5346(16) 24050 8706 nmt -1.0000 -0.0001 -0.5450 0.0000 -1.0002 -0.0000
0.0000 0.0001 0.9999

_twin_special_details            
;
Component 2 rotated by 179.9987° 
around [-0.26 0.00 0.96] (reciprocal) or [0.00 0.00 1.00] (direct)
;
