data_170427_s2_tjl
_audit_creation_date              2017-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number      '2014/7'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety          'C21 H24 Cl N O4'
_chemical_formula_sum             'C21 H24 Cl N O4'
_chemical_formula_weight          389.86
_chemical_absolute_configuration  unk
_chemical_melting_point           ?
_chemical_oxdiff_formula          c12h12n2o3
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            5
_space_group_name_H-M_alt         'I 1 2 1'
_space_group_name_Hall            'I 2y'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z'
 'x+1/2, y+1/2, z+1/2'
 '-x+1/2, y+1/2, -z+1/2'

_cell_length_a                    7.3616(5)
_cell_length_b                    8.6802(4)
_cell_length_c                    31.9635(16)
_cell_angle_alpha                 90
_cell_angle_beta                  92.700(6)
_cell_angle_gamma                 90
_cell_volume                      2040.2(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     1718
_cell_measurement_temperature     293(2)
_cell_measurement_theta_max       26.6050
_cell_measurement_theta_min       3.7980
_shelx_estimated_absorpt_T_max    0.949
_shelx_estimated_absorpt_T_min    0.920
_exptl_absorpt_coefficient_mu     0.213
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.93343
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             ?
_exptl_crystal_density_diffrn     1.269
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        ''
_exptl_crystal_F_000              824
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.35
_exptl_crystal_size_min           0.25
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0176
_diffrn_reflns_av_unetI/netI      0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_l_max        39
_diffrn_reflns_limit_l_min        -38
_diffrn_reflns_number             4568
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          26.372
_diffrn_reflns_theta_min          3.028
_diffrn_ambient_temperature       293.15
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  16.0874
_diffrn_detector_type             Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   41.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   19.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -150.0000 30
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'Xcalibur, Eos'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_UB_11       0.0921129000
_diffrn_orient_matrix_UB_12       0.0054570000
_diffrn_orient_matrix_UB_13       0.0073859000
_diffrn_orient_matrix_UB_21       -0.0276948000
_diffrn_orient_matrix_UB_22       -0.0007094000
_diffrn_orient_matrix_UB_23       0.0209487000
_diffrn_orient_matrix_UB_31       0.0064035000
_diffrn_orient_matrix_UB_32       -0.0815867000
_diffrn_orient_matrix_UB_33       0.0003280000
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage          0.408
_reflns_Friedel_fraction_full     0.502
_reflns_Friedel_fraction_max      0.468
_reflns_number_gt                 2663
_reflns_number_total              3139
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max          0.178
_refine_diff_density_min          -0.178
_refine_diff_density_rms          0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.05(4)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      249
_refine_ls_number_reflns          3139
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0517
_refine_ls_R_factor_gt            0.0412
_refine_ls_restrained_S_all       1.052
_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)+(0.0455P)²+0.2043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0899
_refine_ls_wR_factor_ref          0.0983
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C8(H8), C13(H13), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Cl1 Cl 0.26379(17) 0.38665(10) 0.52034(3) 0.0650(3) Uani 1 1 d . . . . .
 O1 O 0.3453(4) 0.5157(3) 0.60477(7) 0.0494(6) Uani 1 1 d . . . . .
 O2 O 0.3580(4) 0.0488(2) 0.67729(7) 0.0511(7) Uani 1 1 d . . . . .
 O3 O 0.3725(3) 0.3613(2) 0.67934(6) 0.0399(5) Uani 1 1 d . . . . .
 O4 O 0.0798(3) 0.3156(4) 0.66121(8) 0.0640(8) Uani 1 1 d . . . . .
 N1 N 0.2973(4) -0.1960(3) 0.56555(8) 0.0375(6) Uani 1 1 d . . . . .
 H1 H 0.2966 -0.2950 0.5657 0.045 Uiso 1 1 calc R . . . .
 C1 C 0.3134(5) 0.2853(4) 0.56636(9) 0.0395(8) Uani 1 1 d . . . . .
 C2 C 0.3500(4) 0.3737(4) 0.60294(9) 0.0382(7) Uani 1 1 d . . . . .
 C3 C 0.4210(4) 0.2837(4) 0.64205(9) 0.0336(7) Uani 1 1 d . . . . .
 C4 C 0.3636(4) 0.1149(4) 0.64387(10) 0.0345(7) Uani 1 1 d . . . . .
 C5 C 0.3332(4) 0.0372(4) 0.60336(9) 0.0320(7) Uani 1 1 d . . . . .
 C6 C 0.3260(4) -0.1204(4) 0.60171(8) 0.0344(7) Uani 1 1 d . . . . .
 H6 H 0.3415 -0.1764 0.6264 0.041 Uiso 1 1 calc R . . . .
 C7 C 0.2689(4) -0.1190(4) 0.52815(9) 0.0373(7) Uani 1 1 d . . . . .
 C8 C 0.2714(5) 0.0378(4) 0.52819(9) 0.0412(9) Uani 1 1 d . . . . .
 H8 H 0.2496 0.0899 0.5030 0.049 Uiso 1 1 calc R . . . .
 C9 C 0.3064(4) 0.1248(4) 0.56553(9) 0.0342(8) Uani 1 1 d . . . . .
 C10 C 0.6287(5) 0.2842(4) 0.64339(11) 0.0501(9) Uani 1 1 d . . . . .
 H10A H 0.6719 0.3885 0.6444 0.075 Uiso 1 1 calc GR . . . .
 H10B H 0.6703 0.2345 0.6188 0.075 Uiso 1 1 calc GR . . . .
 H10C H 0.6744 0.2298 0.6678 0.075 Uiso 1 1 calc GR . . . .
 C11 C 0.1924(5) 0.3688(4) 0.68558(10) 0.0474(9) Uani 1 1 d . . . . .
 C12 C 0.1586(7) 0.4484(6) 0.72563(12) 0.0780(15) Uani 1 1 d . . . . .
 H12A H 0.2016 0.3853 0.7487 0.117 Uiso 1 1 calc GR . . . .
 H12B H 0.0305 0.4662 0.7275 0.117 Uiso 1 1 calc GR . . . .
 H12C H 0.2218 0.5452 0.7266 0.117 Uiso 1 1 calc GR . . . .
 C13 C 0.2356(5) -0.2147(4) 0.49112(10) 0.0416(8) Uani 1 1 d . . . . .
 H13 H 0.2187 -0.3196 0.4953 0.050 Uiso 1 1 calc R . . . .
 C14 C 0.2272(5) -0.1644(4) 0.45176(10) 0.0430(8) Uani 1 1 d . . . . .
 H14 H 0.2485 -0.0600 0.4477 0.052 Uiso 1 1 calc R . . . .
 C15 C 0.1882(5) -0.2566(4) 0.41453(10) 0.0407(8) Uani 1 1 d . . . . .
 C16 C 0.1932(5) -0.1880(4) 0.37680(10) 0.0504(9) Uani 1 1 d . . . . .
 H16 H 0.2194 -0.0831 0.3774 0.060 Uiso 1 1 calc R . . . .
 C17 C 0.1627(5) -0.2563(4) 0.33414(10) 0.0473(9) Uani 1 1 d . . . . .
 H17 H 0.1092 -0.3589 0.3369 0.057 Uiso 1 1 calc R . . . .
 C18 C 0.3419(5) -0.2720(5) 0.31299(12) 0.0610(11) Uani 1 1 d . . . . .
 H18A H 0.4265 -0.3282 0.3315 0.073 Uiso 1 1 calc R . . . .
 H18B H 0.3919 -0.1700 0.3090 0.073 Uiso 1 1 calc R . . . .
 C19 C 0.3277(6) -0.3537(6) 0.27100(13) 0.0779(14) Uani 1 1 d . . . . .
 H19A H 0.2385 -0.3030 0.2530 0.117 Uiso 1 1 calc GR . . . .
 H19B H 0.2921 -0.4589 0.2750 0.117 Uiso 1 1 calc GR . . . .
 H19C H 0.4435 -0.3509 0.2584 0.117 Uiso 1 1 calc GR . . . .
 C20 C 0.1448(6) -0.4224(4) 0.42019(11) 0.0544(10) Uani 1 1 d . . . . .
 H20A H 0.2542 -0.4777 0.4279 0.082 Uiso 1 1 calc GR . . . .
 H20B H 0.0925 -0.4633 0.3945 0.082 Uiso 1 1 calc GR . . . .
 H20C H 0.0597 -0.4331 0.4419 0.082 Uiso 1 1 calc GR . . . .
 C21 C 0.0298(7) -0.1553(7) 0.30856(13) 0.0858(16) Uani 1 1 d . . . . .
 H21A H -0.0832 -0.1494 0.3223 0.129 Uiso 1 1 calc GR . . . .
 H21B H 0.0088 -0.1991 0.2812 0.129 Uiso 1 1 calc GR . . . .
 H21C H 0.0798 -0.0538 0.3061 0.129 Uiso 1 1 calc GR . . . .


_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
 Cl1 C1 1.738(3) . ?
 O1 C2 1.234(4) . ?
 O2 C4 1.215(4) . ?
 O3 C3 1.429(3) . ?
 O3 C11 1.351(4) . ?
 O4 C11 1.203(4) . ?
 N1 H1 0.8600 . ?
 N1 C6 1.337(4) . ?
 N1 C7 1.377(4) . ?
 C1 C2 1.414(4) . ?
 C1 C9 1.395(4) . ?
 C2 C3 1.545(4) . ?
 C3 C4 1.527(4) . ?
 C3 C10 1.527(4) . ?
 C4 C5 1.468(4) . ?
 C5 C6 1.370(5) . ?
 C5 C9 1.434(4) . ?
 C6 H6 0.9300 . ?
 C7 C8 1.361(5) . ?
 C7 C13 1.457(4) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.425(4) . ?
 C10 H10A 0.9600 . ?
 C10 H10B 0.9600 . ?
 C10 H10C 0.9600 . ?
 C11 C12 1.486(5) . ?
 C12 H12A 0.9600 . ?
 C12 H12B 0.9600 . ?
 C12 H12C 0.9600 . ?
 C13 H13 0.9300 . ?
 C13 C14 1.330(4) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.452(4) . ?
 C15 C16 1.347(4) . ?
 C15 C20 1.487(5) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.494(4) . ?
 C17 H17 0.9800 . ?
 C17 C18 1.516(5) . ?
 C17 C21 1.523(5) . ?
 C18 H18A 0.9700 . ?
 C18 H18B 0.9700 . ?
 C18 C19 1.517(5) . ?
 C19 H19A 0.9600 . ?
 C19 H19B 0.9600 . ?
 C19 H19C 0.9600 . ?
 C20 H20A 0.9600 . ?
 C20 H20B 0.9600 . ?
 C20 H20C 0.9600 . ?
 C21 H21A 0.9600 . ?
 C21 H21B 0.9600 . ?
 C21 H21C 0.9600 . ?

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
 C11 O3 C3 115.6(3) . . ?
 C6 N1 H1 119.2 . . ?
 C6 N1 C7 121.6(3) . . ?
 C7 N1 H1 119.2 . . ?
 C2 C1 Cl1 116.7(2) . . ?
 C9 C1 Cl1 118.9(3) . . ?
 C9 C1 C2 124.3(3) . . ?
 O1 C2 C1 125.2(3) . . ?
 O1 C2 C3 118.4(3) . . ?
 C1 C2 C3 116.1(3) . . ?
 O3 C3 C2 110.4(2) . . ?
 O3 C3 C4 109.9(2) . . ?
 O3 C3 C10 105.4(3) . . ?
 C4 C3 C2 115.6(3) . . ?
 C4 C3 C10 106.3(3) . . ?
 C10 C3 C2 108.7(3) . . ?
 O2 C4 C3 120.5(3) . . ?
 O2 C4 C5 123.3(3) . . ?
 C5 C4 C3 116.0(3) . . ?
 C6 C5 C4 119.8(3) . . ?
 C6 C5 C9 119.5(3) . . ?
 C9 C5 C4 120.6(3) . . ?
 N1 C6 C5 121.8(3) . . ?
 N1 C6 H6 119.1 . . ?
 C5 C6 H6 119.1 . . ?
 N1 C7 C13 116.2(3) . . ?
 C8 C7 N1 118.9(3) . . ?
 C8 C7 C13 124.9(3) . . ?
 C7 C8 H8 118.9 . . ?
 C7 C8 C9 122.2(3) . . ?
 C9 C8 H8 118.9 . . ?
 C1 C9 C5 120.7(3) . . ?
 C1 C9 C8 123.4(3) . . ?
 C8 C9 C5 115.9(3) . . ?
 C3 C10 H10A 109.5 . . ?
 C3 C10 H10B 109.5 . . ?
 C3 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 O3 C11 C12 110.8(3) . . ?
 O4 C11 O3 122.5(3) . . ?
 O4 C11 C12 126.7(4) . . ?
 C11 C12 H12A 109.5 . . ?
 C11 C12 H12B 109.5 . . ?
 C11 C12 H12C 109.5 . . ?
 H12A C12 H12B 109.5 . . ?
 H12A C12 H12C 109.5 . . ?
 H12B C12 H12C 109.5 . . ?
 C7 C13 H13 117.3 . . ?
 C14 C13 C7 125.4(3) . . ?
 C14 C13 H13 117.3 . . ?
 C13 C14 H14 116.8 . . ?
 C13 C14 C15 126.3(3) . . ?
 C15 C14 H14 116.8 . . ?
 C14 C15 C20 118.0(3) . . ?
 C16 C15 C14 118.5(3) . . ?
 C16 C15 C20 123.5(3) . . ?
 C15 C16 H16 115.4 . . ?
 C15 C16 C17 129.2(3) . . ?
 C17 C16 H16 115.4 . . ?
 C16 C17 H17 108.7 . . ?
 C16 C17 C18 110.3(3) . . ?
 C16 C17 C21 109.1(3) . . ?
 C18 C17 H17 108.7 . . ?
 C18 C17 C21 111.3(3) . . ?
 C21 C17 H17 108.7 . . ?
 C17 C18 H18A 108.7 . . ?
 C17 C18 H18B 108.7 . . ?
 C17 C18 C19 114.3(3) . . ?
 H18A C18 H18B 107.6 . . ?
 C19 C18 H18A 108.7 . . ?
 C19 C18 H18B 108.7 . . ?
 C18 C19 H19A 109.5 . . ?
 C18 C19 H19B 109.5 . . ?
 C18 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 C15 C20 H20A 109.5 . . ?
 C15 C20 H20B 109.5 . . ?
 C15 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C17 C21 H21A 109.5 . . ?
 C17 C21 H21B 109.5 . . ?
 C17 C21 H21C 109.5 . . ?
 H21A C21 H21B 109.5 . . ?
 H21A C21 H21C 109.5 . . ?
 H21B C21 H21C 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Cl1 C1 C2 O1 1.7(5) . . . . ?
 Cl1 C1 C2 C3 -171.4(2) . . . . ?
 Cl1 C1 C9 C5 -175.4(2) . . . . ?
 Cl1 C1 C9 C8 4.0(5) . . . . ?
 O1 C2 C3 O3 33.9(4) . . . . ?
 O1 C2 C3 C4 159.3(3) . . . . ?
 O1 C2 C3 C10 -81.2(4) . . . . ?
 O2 C4 C5 C6 -10.6(5) . . . . ?
 O2 C4 C5 C9 167.8(3) . . . . ?
 O3 C3 C4 O2 -29.8(4) . . . . ?
 O3 C3 C4 C5 155.6(3) . . . . ?
 N1 C7 C8 C9 1.4(5) . . . . ?
 N1 C7 C13 C14 -171.3(3) . . . . ?
 C1 C2 C3 O3 -152.5(3) . . . . ?
 C1 C2 C3 C4 -27.1(4) . . . . ?
 C1 C2 C3 C10 92.4(3) . . . . ?
 C2 C1 C9 C5 1.4(6) . . . . ?
 C2 C1 C9 C8 -179.2(3) . . . . ?
 C2 C3 C4 O2 -155.5(3) . . . . ?
 C2 C3 C4 C5 29.9(4) . . . . ?
 C3 O3 C11 O4 -0.9(5) . . . . ?
 C3 O3 C11 C12 178.7(3) . . . . ?
 C3 C4 C5 C6 163.8(3) . . . . ?
 C3 C4 C5 C9 -17.7(5) . . . . ?
 C4 C5 C6 N1 179.5(3) . . . . ?
 C4 C5 C9 C1 1.7(5) . . . . ?
 C4 C5 C9 C8 -177.8(3) . . . . ?
 C6 N1 C7 C8 0.4(5) . . . . ?
 C6 N1 C7 C13 -178.8(3) . . . . ?
 C6 C5 C9 C1 -179.9(3) . . . . ?
 C6 C5 C9 C8 0.7(5) . . . . ?
 C7 N1 C6 C5 -1.6(5) . . . . ?
 C7 C8 C9 C1 178.7(3) . . . . ?
 C7 C8 C9 C5 -1.9(5) . . . . ?
 C7 C13 C14 C15 -177.8(3) . . . . ?
 C8 C7 C13 C14 9.6(6) . . . . ?
 C9 C1 C2 O1 -175.1(3) . . . . ?
 C9 C1 C2 C3 11.8(5) . . . . ?
 C9 C5 C6 N1 1.0(5) . . . . ?
 C10 C3 C4 O2 83.7(4) . . . . ?
 C10 C3 C4 C5 -90.9(3) . . . . ?
 C11 O3 C3 C2 65.4(3) . . . . ?
 C11 O3 C3 C4 -63.3(3) . . . . ?
 C11 O3 C3 C10 -177.4(3) . . . . ?
 C13 C7 C8 C9 -179.5(3) . . . . ?
 C13 C14 C15 C16 -177.0(3) . . . . ?
 C13 C14 C15 C20 2.9(6) . . . . ?
 C14 C15 C16 C17 178.6(3) . . . . ?
 C15 C16 C17 C18 -106.1(5) . . . . ?
 C15 C16 C17 C21 131.4(5) . . . . ?
 C16 C17 C18 C19 174.7(4) . . . . ?
 C20 C15 C16 C17 -1.4(6) . . . . ?
 C21 C17 C18 C19 -64.1(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
