data_mo_dd03s_0m
_audit_creation_date               2020-03-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number       '2018/3'
loop_
  _audit_author_name
  _audit_author_email
  _audit_author_address
 'Sarlah, D.' sarlah@illinois.edu
;
University of Illinois at Urbana-Champaign
Department of Chemistry
600 S. Mathews Ave
Urbana
61801
USA
;
 'Shved, A.S.' shvedalx@illinois.edu
;
University of Illinois at Urbana-Champaign
Department of Chemistry
600 S. Mathews Ave
Urbana
61801
USA
;

_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic         
 (5S*,10R*,12R*,14S*)-6-chloro-2-methyl-5,10-dihydro-1H-5,10-[2,3]epoxireno[1,2,4]triazolo[1,2-b]phthalazine-1,3(2H)-dione
_chemical_formula_moiety           'C13 H10 Cl N3 O3'
_chemical_formula_sum              'C13 H10 Cl N3 O3'
_chemical_formula_weight           291.69
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 '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        'orthorhombic'
_space_group_IT_number             61
_space_group_name_H-M_alt          'P b c a'
_space_group_name_Hall             '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                     6.8955(2)
_cell_length_b                     15.5594(4)
_cell_length_c                     21.9079(6)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2350.50(11)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      9905
_cell_measurement_temperature      100.01
_cell_measurement_theta_max        28.283
_cell_measurement_theta_min        2.779
_shelx_estimated_absorpt_T_max     0.971
_shelx_estimated_absorpt_T_min     0.911
_exptl_absorpt_coefficient_mu      0.337
_exptl_absorpt_correction_T_max    0.7457
_exptl_absorpt_correction_T_min    0.6542
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0847 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8773.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.649
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1200
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 -1.00 0.00 0.00 0.0630
 0.00 1.00 -1.00 0.1110
 0.00 -1.00 1.00 0.1100
 0.00 -1.00 -1.00 0.0920
 0.00 1.00 1.00 0.1180
 1.00 0.00 -2.00 0.0460
 -1.00 0.00 2.00 0.0540
 0.00 0.00 -1.00 0.0340
 0.00 0.00 1.00 0.0440
 1.00 0.00 2.00 0.0500

_exptl_crystal_preparation         ?
_exptl_crystal_recrystallization_method  'Rerystallized from hot ethanol'
_exptl_crystal_size_max            0.281
_exptl_crystal_size_mid            0.126
_exptl_crystal_size_min            0.089
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0470
_diffrn_reflns_av_unetI/netI       0.0233
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         20
_diffrn_reflns_limit_k_min         -20
_diffrn_reflns_limit_l_max         29
_diffrn_reflns_limit_l_min         -29
_diffrn_reflns_number              27140
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.320
_diffrn_reflns_theta_min           2.618
_diffrn_ambient_temperature        100.01
_diffrn_detector                   'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean   ?
_diffrn_detector_type              'charge integrated pixel array'
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device         'kappa diffractometer'
_diffrn_measurement_device_type    DUO_PhotonII_Mo
_diffrn_measurement_method         'profile data from φ and ω scans'
_diffrn_radiation_monochromator    'multilayer mirrors'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_current             1.0
_diffrn_source_power               0.05
_diffrn_source_target              Mo
_diffrn_source_type                'Incoatec I\ms'
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2534
_reflns_number_total               2925
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max           0.319
_refine_diff_density_min           -0.247
_refine_diff_density_rms           0.052
_refine_ls_extinction_coef         0.0048(5)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.099
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       305
_refine_ls_number_reflns           2925
_refine_ls_number_restraints       756
_refine_ls_R_factor_all            0.0418
_refine_ls_R_factor_gt             0.0335
_refine_ls_restrained_S_all        0.994
_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)+(0.0294P)²+1.8961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0788
_refine_ls_wR_factor_ref           0.0826
_refine_special_details           
 'Initial refinement revealed a large unaccounted electron density spot right next to H9a. Upon manually fitting an idealized geometry of enantiomeric model so that the chlorine would occupy that spot, the whole molecule disorder could be refined to show about 7% occupancy of the respective atoms.'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1B-C6B \\sim Cl1A-C6A
 with sigma of 0.01
 O1B-C2B \\sim O1A-C3A \\sim O1B-C3B \\sim O1A-C2A
 with sigma of 0.01
 O3B-C11B \\sim O3A-C12A \\sim O2B-C12B \\sim O2A-C11A
 with sigma of 0.01
 C8B-C7B \\sim C8A-C7A
 with sigma of 0.01
 C8B-C9B \\sim C6A-C7A \\sim C6B-C7B \\sim C8A-C9A
 with sigma of 0.01
 N3B-C13B \\sim N3A-C13A
 with sigma of 0.01
 C9B-C10B \\sim C6A-C5A \\sim C6B-C5B \\sim C9A-C10A
 with sigma of 0.01
 N2B-N1B \\sim N1A-N2A
 with sigma of 0.01
 C10B-C5B \\sim C10A-C5A
 with sigma of 0.01
 N2B-C11B \\sim N2A-C12A \\sim N1B-C12B \\sim N1A-C11A
 with sigma of 0.01
 C10B-C1B \\sim C4A-C5A \\sim C4B-C5B \\sim C10A-C1A
 with sigma of 0.01
 N3B-C11B \\sim N3A-C12A \\sim N3B-C12B \\sim N3A-C11A
 with sigma of 0.01
 N2B-C1B \\sim N2A-C4A \\sim N1B-C4B \\sim N1A-C1A
 with sigma of 0.01
 C2B-C3B \\sim C2A-C3A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(C13B) = Uanis(C13A)
4. Others
 Sof(Cl1B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(N1B)=Sof(N2B)=Sof(N3B)=Sof(C1B)=
 Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=
 Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=
 Sof(C11B)=Sof(C12B)=Sof(C13B)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(Cl1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(N1A)=Sof(N2A)=Sof(N3A)=Sof(C1A)=
 Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(C11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Free rotating group:
 Cl1B(O1B,O2B,O3B,N1B,N2B,N3B,C1B,C2B,C3B,C4B,C5B,C6B,C7B,C8B,C9B,C10B,C11B,
 C12B,C13B)
5.b Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C7B(H7B), C8B(H8B), C9B(H9B)
5.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Cl1A Cl 0.77519(5) 0.46306(2) 0.75502(2) 0.01667(12) Uani 0.9328(17) 1 d D U P A
 1
 O1A O 0.31651(19) 0.54086(9) 0.60787(6) 0.0182(3) Uani 0.9328(17) 1 d D U P A
 1
 O2A O 0.9218(3) 0.73901(11) 0.52172(9) 0.0212(4) Uani 0.9328(17) 1 d D U P A
 1
 O3A O 0.8774(3) 0.72776(12) 0.73044(8) 0.0197(3) Uani 0.9328(17) 1 d D U P A
 1
 N1A N 0.6761(2) 0.69587(9) 0.58742(7) 0.0140(3) Uani 0.9328(17) 1 d D U P A 1
 N2A N 0.6628(2) 0.69127(9) 0.65294(7) 0.0131(3) Uani 0.9328(17) 1 d D U P A 1
 N3A N 0.9384(3) 0.75446(10) 0.62740(8) 0.0152(3) Uani 0.9328(17) 1 d D U P A
 1
 C1A C 0.5944(3) 0.61872(10) 0.55713(8) 0.0150(3) Uani 0.9328(17) 1 d D U P A
 1
 H1A H 0.604564 0.622202 0.511662 0.018 Uiso 0.9328(17) 1 calc R U P A 1
 C2A C 0.3830(3) 0.61876(11) 0.57881(8) 0.0173(3) Uani 0.9328(17) 1 d D U P A
 1
 H2A H 0.286749 0.655580 0.556851 0.021 Uiso 0.9328(17) 1 calc R U P A 1
 C3A C 0.3720(2) 0.61263(11) 0.64554(8) 0.0155(3) Uani 0.9328(17) 1 d D U P A
 1
 H3A H 0.268038 0.645425 0.667235 0.019 Uiso 0.9328(17) 1 calc R U P A 1
 C4A C 0.5752(2) 0.60925(10) 0.67416(7) 0.0127(3) Uani 0.9328(17) 1 d D U P A
 1
 H4A H 0.570336 0.605264 0.719693 0.015 Uiso 0.9328(17) 1 calc R U P A 1
 C5A C 0.6902(2) 0.53710(10) 0.64607(7) 0.0128(3) Uani 0.9328(17) 1 d D U P A
 1
 C6A C 0.7857(2) 0.47071(10) 0.67590(7) 0.0133(3) Uani 0.9328(17) 1 d D U P A
 1
 C7A C 0.8891(2) 0.40941(10) 0.64297(8) 0.0146(3) Uani 0.9328(17) 1 d D U P A
 1
 H7A H 0.954661 0.364227 0.663575 0.018 Uiso 0.9328(17) 1 calc R U P A 1
 C8A C 0.8954(2) 0.41490(10) 0.57958(8) 0.0177(3) Uani 0.9328(17) 1 d D U P A
 1
 H8A H 0.964790 0.372840 0.556963 0.021 Uiso 0.9328(17) 1 calc R U P A 1
 C9A C 0.8013(2) 0.48133(10) 0.54889(7) 0.0167(3) Uani 0.9328(17) 1 d D U P A
 1
 H9A H 0.806742 0.485063 0.505639 0.020 Uiso 0.9328(17) 1 calc R U P A 1
 C10A C 0.6998(2) 0.54173(10) 0.58238(7) 0.0144(3) Uani 0.9328(17) 1 d D U P A
 1
 C11A C 0.8544(3) 0.72999(10) 0.57263(8) 0.0153(4) Uani 0.9328(17) 1 d D U P A
 1
 C12A C 0.8327(3) 0.72409(11) 0.67693(8) 0.0146(3) Uani 0.9328(17) 1 d D U P A
 1
 C13A C 1.1099(3) 0.80879(12) 0.63218(10) 0.0201(4) Uani 0.9328(17) 1 d D U P A
 1
 H13A H 1.071820 0.869238 0.628389 0.030 Uiso 0.9328(17) 1 calc R U P A 1
 H13B H 1.201109 0.794124 0.599506 0.030 Uiso 0.9328(17) 1 calc R U P A 1
 H13C H 1.172004 0.799536 0.671876 0.030 Uiso 0.9328(17) 1 calc R U P A 1
 Cl1B Cl 0.8200(15) 0.4699(7) 0.4970(4) 0.075(4) Uani 0.0672(17) 1 d DG U P A
 2
 O1B O 0.3187(12) 0.5507(10) 0.6284(5) 0.018(3) Uani 0.0672(17) 1 d DG U P A 2
 O2B O 0.936(3) 0.7320(6) 0.5299(7) 0.013(5) Uani 0.0672(17) 1 d DG U P A 2
 O3B O 0.907(3) 0.7351(9) 0.7391(7) 0.021(5) Uani 0.0672(17) 1 d DG U P A 2
 N1B N 0.692(2) 0.6966(5) 0.5985(5) 0.014(2) Uani 0.0672(17) 1 d DG U P A 2
 N2B N 0.682(2) 0.6989(6) 0.6643(5) 0.014(2) Uani 0.0672(17) 1 d DG U P A 2
 N3B N 0.963(3) 0.7540(6) 0.6348(7) 0.015(3) Uani 0.0672(17) 1 d DG U P A 2
 C1B C 0.5836(18) 0.6217(7) 0.6900(4) 0.014(2) Uani 0.0672(17) 1 d DG U P A 2
 H1B H 0.578039 0.623186 0.735599 0.017 Uiso 0.0672(17) 1 calc R U P A 2
 C2B C 0.3814(17) 0.6263(9) 0.6612(5) 0.016(2) Uani 0.0672(17) 1 d DG U P A 2
 H2B H 0.281172 0.663930 0.680531 0.019 Uiso 0.0672(17) 1 calc R U P A 2
 C3B C 0.3929(16) 0.6230(8) 0.5941(5) 0.016(2) Uani 0.0672(17) 1 d DG U P A 2
 H3B H 0.300228 0.658474 0.569615 0.020 Uiso 0.0672(17) 1 calc R U P A 2
 C4B C 0.6050(16) 0.6169(6) 0.5731(4) 0.017(2) Uani 0.0672(17) 1 d DG U P A 2
 H4B H 0.616249 0.614402 0.527637 0.020 Uiso 0.0672(17) 1 calc R U P A 2
 C5B C 0.7028(11) 0.5420(5) 0.6034(4) 0.012(2) Uani 0.0672(17) 1 d DG U P A 2
 C6B C 0.8036(11) 0.4748(5) 0.5759(4) 0.020(2) Uani 0.0672(17) 1 d DG U P A 2
 C7B C 0.8899(14) 0.4106(5) 0.6109(5) 0.014(2) Uani 0.0672(17) 1 d DG U P A 2
 H7B H 0.958655 0.365129 0.591717 0.017 Uiso 0.0672(17) 1 calc R U P A 2
 C8B C 0.8747(17) 0.4137(7) 0.6745(5) 0.023(3) Uani 0.0672(17) 1 d DG U P A 2
 H8B H 0.932391 0.369778 0.698553 0.027 Uiso 0.0672(17) 1 calc R U P A 2
 C9B C 0.7752(17) 0.4808(7) 0.7030(4) 0.016(2) Uani 0.0672(17) 1 d DG U P A 2
 H9B H 0.765107 0.483199 0.746194 0.019 Uiso 0.0672(17) 1 calc R U P A 2
 C10B C 0.6909(14) 0.5443(6) 0.6668(4) 0.016(2) Uani 0.0672(17) 1 d DG U P A
 2
 C11B C 0.857(2) 0.7288(7) 0.6856(6) 0.015(3) Uani 0.0672(17) 1 d DG U P A 2
 C12B C 0.871(2) 0.7271(5) 0.5813(6) 0.014(3) Uani 0.0672(17) 1 d DG U P A 2
 C13B C 1.138(3) 0.8056(9) 0.6370(9) 0.0201(4) Uani 0.0672(17) 1 d DG U P A 2
 H13D H 1.245885 0.773308 0.618792 0.030 Uiso 0.0672(17) 1 calc R U P A 2
 H13E H 1.169359 0.819380 0.679498 0.030 Uiso 0.0672(17) 1 calc R U P A 2
 H13F H 1.118243 0.858945 0.614018 0.030 Uiso 0.0672(17) 1 calc R U P A 2


_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 C6A 1.7389(16) . ?
 O1A C2A 1.4438(19) . ?
 O1A C3A 1.4403(19) . ?
 O2A C11A 1.216(2) . ?
 O3A C12A 1.213(2) . ?
 N1A N2A 1.4401(18) . ?
 N1A C1A 1.483(2) . ?
 N1A C11A 1.378(2) . ?
 N2A C4A 1.4866(19) . ?
 N2A C12A 1.382(2) . ?
 N3A C11A 1.386(2) . ?
 N3A C12A 1.390(2) . ?
 N3A C13A 1.457(2) . ?
 C1A H1A 1.0000 . ?
 C1A C2A 1.533(2) . ?
 C1A C10A 1.506(2) . ?
 C2A H2A 1.0000 . ?
 C2A C3A 1.467(2) . ?
 C3A H3A 1.0000 . ?
 C3A C4A 1.536(2) . ?
 C4A H4A 1.0000 . ?
 C4A C5A 1.506(2) . ?
 C5A C6A 1.389(2) . ?
 C5A C10A 1.399(2) . ?
 C6A C7A 1.392(2) . ?
 C7A H7A 0.9500 . ?
 C7A C8A 1.392(2) . ?
 C8A H8A 0.9500 . ?
 C8A C9A 1.394(2) . ?
 C9A H9A 0.9500 . ?
 C9A C10A 1.383(2) . ?
 C13A H13A 0.9800 . ?
 C13A H13B 0.9800 . ?
 C13A H13C 0.9800 . ?
 Cl1B C6B 1.7335 . ?
 O1B C2B 1.4444 . ?
 O1B C3B 1.4458 . ?
 O2B C12B 1.2126 . ?
 O3B C11B 1.2262 . ?
 N1B N2B 1.4439 . ?
 N1B C4B 1.4866 . ?
 N1B C12B 1.3760 . ?
 N2B C1B 1.4895 . ?
 N2B C11B 1.3757 . ?
 N3B C11B 1.3861 . ?
 N3B C12B 1.3945 . ?
 N3B C13B 1.4542 . ?
 C1B H1B 1.0000 . ?
 C1B C2B 1.5327 . ?
 C1B C10B 1.5025 . ?
 C2B H2B 1.0000 . ?
 C2B C3B 1.4722 . ?
 C3B H3B 1.0000 . ?
 C3B C4B 1.5363 . ?
 C4B H4B 1.0000 . ?
 C4B C5B 1.5009 . ?
 C5B C6B 1.3920 . ?
 C5B C10B 1.3920 . ?
 C6B C7B 1.3928 . ?
 C7B H7B 0.9500 . ?
 C7B C8B 1.3983 . ?
 C8B H8B 0.9500 . ?
 C8B C9B 1.3969 . ?
 C9B H9B 0.9500 . ?
 C9B C10B 1.3933 . ?
 C13B H13D 0.9800 . ?
 C13B H13E 0.9800 . ?
 C13B H13F 0.9800 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C3A O1A C2A 61.15(10) . . ?
 N2A N1A C1A 112.43(12) . . ?
 C11A N1A N2A 108.09(13) . . ?
 C11A N1A C1A 123.09(13) . . ?
 N1A N2A C4A 112.35(12) . . ?
 C12A N2A N1A 107.87(12) . . ?
 C12A N2A C4A 122.87(13) . . ?
 C11A N3A C12A 111.31(14) . . ?
 C11A N3A C13A 124.11(14) . . ?
 C12A N3A C13A 124.52(14) . . ?
 N1A C1A H1A 112.0 . . ?
 N1A C1A C2A 102.85(13) . . ?
 N1A C1A C10A 107.22(13) . . ?
 C2A C1A H1A 112.0 . . ?
 C10A C1A H1A 112.0 . . ?
 C10A C1A C2A 110.19(13) . . ?
 O1A C2A C1A 115.98(14) . . ?
 O1A C2A H2A 118.8 . . ?
 O1A C2A C3A 59.31(10) . . ?
 C1A C2A H2A 118.8 . . ?
 C3A C2A C1A 110.97(14) . . ?
 C3A C2A H2A 118.8 . . ?
 O1A C3A C2A 59.54(10) . . ?
 O1A C3A H3A 118.5 . . ?
 O1A C3A C4A 116.73(13) . . ?
 C2A C3A H3A 118.5 . . ?
 C2A C3A C4A 111.22(14) . . ?
 C4A C3A H3A 118.5 . . ?
 N2A C4A C3A 102.34(12) . . ?
 N2A C4A H4A 112.3 . . ?
 N2A C4A C5A 107.34(12) . . ?
 C3A C4A H4A 112.3 . . ?
 C5A C4A C3A 109.83(13) . . ?
 C5A C4A H4A 112.3 . . ?
 C6A C5A C4A 127.74(14) . . ?
 C6A C5A C10A 119.04(14) . . ?
 C10A C5A C4A 113.21(13) . . ?
 C5A C6A Cl1A 120.01(12) . . ?
 C5A C6A C7A 120.57(14) . . ?
 C7A C6A Cl1A 119.41(12) . . ?
 C6A C7A H7A 120.3 . . ?
 C6A C7A C8A 119.41(14) . . ?
 C8A C7A H7A 120.3 . . ?
 C7A C8A H8A 119.6 . . ?
 C7A C8A C9A 120.81(15) . . ?
 C9A C8A H8A 119.6 . . ?
 C8A C9A H9A 120.5 . . ?
 C10A C9A C8A 118.94(14) . . ?
 C10A C9A H9A 120.5 . . ?
 C5A C10A C1A 112.62(13) . . ?
 C9A C10A C1A 126.14(14) . . ?
 C9A C10A C5A 121.22(14) . . ?
 O2A C11A N1A 126.94(16) . . ?
 O2A C11A N3A 127.06(16) . . ?
 N1A C11A N3A 105.98(13) . . ?
 O3A C12A N2A 126.91(16) . . ?
 O3A C12A N3A 127.21(17) . . ?
 N2A C12A N3A 105.85(13) . . ?
 N3A C13A H13A 109.5 . . ?
 N3A C13A H13B 109.5 . . ?
 N3A C13A H13C 109.5 . . ?
 H13A C13A H13B 109.5 . . ?
 H13A C13A H13C 109.5 . . ?
 H13B C13A H13C 109.5 . . ?
 C2B O1B C3B 61.2 . . ?
 N2B N1B C4B 112.0 . . ?
 C12B N1B N2B 108.0 . . ?
 C12B N1B C4B 123.2 . . ?
 N1B N2B C1B 112.3 . . ?
 C11B N2B N1B 107.6 . . ?
 C11B N2B C1B 123.0 . . ?
 C11B N3B C12B 110.6 . . ?
 C11B N3B C13B 124.6 . . ?
 C12B N3B C13B 124.7 . . ?
 N2B C1B H1B 112.1 . . ?
 N2B C1B C2B 102.7 . . ?
 N2B C1B C10B 107.1 . . ?
 C2B C1B H1B 112.1 . . ?
 C10B C1B H1B 112.1 . . ?
 C10B C1B C2B 110.2 . . ?
 O1B C2B C1B 116.0 . . ?
 O1B C2B H2B 118.8 . . ?
 O1B C2B C3B 59.4 . . ?
 C1B C2B H2B 118.8 . . ?
 C3B C2B C1B 111.1 . . ?
 C3B C2B H2B 118.8 . . ?
 O1B C3B C2B 59.3 . . ?
 O1B C3B H3B 118.8 . . ?
 O1B C3B C4B 116.4 . . ?
 C2B C3B H3B 118.8 . . ?
 C2B C3B C4B 110.6 . . ?
 C4B C3B H3B 118.8 . . ?
 N1B C4B C3B 102.8 . . ?
 N1B C4B H4B 112.0 . . ?
 N1B C4B C5B 107.5 . . ?
 C3B C4B H4B 112.0 . . ?
 C5B C4B C3B 110.1 . . ?
 C5B C4B H4B 112.0 . . ?
 C6B C5B C4B 128.1 . . ?
 C6B C5B C10B 118.7 . . ?
 C10B C5B C4B 113.2 . . ?
 C5B C6B Cl1B 119.8 . . ?
 C5B C6B C7B 120.9 . . ?
 C7B C6B Cl1B 119.3 . . ?
 C6B C7B H7B 120.3 . . ?
 C6B C7B C8B 119.5 . . ?
 C8B C7B H7B 120.3 . . ?
 C7B C8B H8B 119.8 . . ?
 C9B C8B C7B 120.5 . . ?
 C9B C8B H8B 119.8 . . ?
 C8B C9B H9B 120.6 . . ?
 C10B C9B C8B 118.7 . . ?
 C10B C9B H9B 120.6 . . ?
 C5B C10B C1B 112.8 . . ?
 C5B C10B C9B 121.7 . . ?
 C9B C10B C1B 125.5 . . ?
 O3B C11B N2B 126.7 . . ?
 O3B C11B N3B 126.7 . . ?
 N2B C11B N3B 106.6 . . ?
 O2B C12B N1B 127.2 . . ?
 O2B C12B N3B 126.6 . . ?
 N1B C12B N3B 106.2 . . ?
 N3B C13B H13D 109.5 . . ?
 N3B C13B H13E 109.5 . . ?
 N3B C13B H13F 109.5 . . ?
 H13D C13B H13E 109.5 . . ?
 H13D C13B H13F 109.5 . . ?
 H13E C13B H13F 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
 Cl1A C6A C7A C8A 179.18(12) . . . . ?
 O1A C2A C3A C4A 109.35(14) . . . . ?
 O1A C3A C4A N2A 124.82(14) . . . . ?
 O1A C3A C4A C5A 11.04(18) . . . . ?
 N1A N2A C4A C3A -61.46(15) . . . . ?
 N1A N2A C4A C5A 54.13(16) . . . . ?
 N1A N2A C12A O3A -177.01(16) . . . . ?
 N1A N2A C12A N3A 4.89(16) . . . . ?
 N1A C1A C2A O1A -125.22(14) . . . . ?
 N1A C1A C2A C3A -60.14(16) . . . . ?
 N1A C1A C10A C5A 55.40(17) . . . . ?
 N1A C1A C10A C9A -123.05(17) . . . . ?
 N2A N1A C1A C2A 59.73(15) . . . . ?
 N2A N1A C1A C10A -56.47(17) . . . . ?
 N2A N1A C11A O2A 175.51(17) . . . . ?
 N2A N1A C11A N3A -6.39(16) . . . . ?
 N2A C4A C5A C6A 122.96(16) . . . . ?
 N2A C4A C5A C10A -55.83(17) . . . . ?
 C1A N1A N2A C4A 1.55(17) . . . . ?
 C1A N1A N2A C12A 140.07(13) . . . . ?
 C1A N1A C11A O2A 41.7(3) . . . . ?
 C1A N1A C11A N3A -140.17(14) . . . . ?
 C1A C2A C3A O1A -108.55(14) . . . . ?
 C1A C2A C3A C4A 0.80(18) . . . . ?
 C2A O1A C3A C4A -100.02(16) . . . . ?
 C2A C1A C10A C5A -55.83(18) . . . . ?
 C2A C1A C10A C9A 125.72(17) . . . . ?
 C2A C3A C4A N2A 59.23(16) . . . . ?
 C2A C3A C4A C5A -54.55(17) . . . . ?
 C3A O1A C2A C1A 100.00(16) . . . . ?
 C3A C4A C5A C6A -126.52(16) . . . . ?
 C3A C4A C5A C10A 54.70(17) . . . . ?
 C4A N2A C12A O3A -43.8(2) . . . . ?
 C4A N2A C12A N3A 138.06(14) . . . . ?
 C4A C5A C6A Cl1A 1.6(2) . . . . ?
 C4A C5A C6A C7A -178.93(15) . . . . ?
 C4A C5A C10A C1A 0.73(19) . . . . ?
 C4A C5A C10A C9A 179.27(14) . . . . ?
 C5A C6A C7A C8A -0.3(2) . . . . ?
 C6A C5A C10A C1A -178.17(14) . . . . ?
 C6A C5A C10A C9A 0.4(2) . . . . ?
 C6A C7A C8A C9A 0.6(2) . . . . ?
 C7A C8A C9A C10A -0.4(2) . . . . ?
 C8A C9A C10A C1A 178.28(16) . . . . ?
 C8A C9A C10A C5A 0.0(2) . . . . ?
 C10A C1A C2A O1A -11.18(19) . . . . ?
 C10A C1A C2A C3A 53.90(17) . . . . ?
 C10A C5A C6A Cl1A -179.65(12) . . . . ?
 C10A C5A C6A C7A -0.2(2) . . . . ?
 C11A N1A N2A C4A -137.58(13) . . . . ?
 C11A N1A N2A C12A 0.94(16) . . . . ?
 C11A N1A C1A C2A -168.22(14) . . . . ?
 C11A N1A C1A C10A 75.59(18) . . . . ?
 C11A N3A C12A O3A 172.68(17) . . . . ?
 C11A N3A C12A N2A -9.23(17) . . . . ?
 C12A N2A C4A C3A 167.18(14) . . . . ?
 C12A N2A C4A C5A -77.23(17) . . . . ?
 C12A N3A C11A O2A -172.07(17) . . . . ?
 C12A N3A C11A N1A 9.83(17) . . . . ?
 C13A N3A C11A O2A 10.9(3) . . . . ?
 C13A N3A C11A N1A -167.24(14) . . . . ?
 C13A N3A C12A O3A -10.3(3) . . . . ?
 C13A N3A C12A N2A 167.81(15) . . . . ?
 Cl1B C6B C7B C8B -179.1 . . . . ?
 O1B C2B C3B C4B -109.2 . . . . ?
 O1B C3B C4B N1B -124.9 . . . . ?
 O1B C3B C4B C5B -10.6 . . . . ?
 N1B N2B C1B C2B -60.1 . . . . ?
 N1B N2B C1B C10B 56.0 . . . . ?
 N1B N2B C11B O3B -175.7 . . . . ?
 N1B N2B C11B N3B 7.0 . . . . ?
 N1B C4B C5B C6B -122.3 . . . . ?
 N1B C4B C5B C10B 56.0 . . . . ?
 N2B N1B C4B C3B 61.6 . . . . ?
 N2B N1B C4B C5B -54.6 . . . . ?
 N2B N1B C12B O2B 177.2 . . . . ?
 N2B N1B C12B N3B -4.6 . . . . ?
 N2B C1B C2B O1B 125.5 . . . . ?
 N2B C1B C2B C3B 60.2 . . . . ?
 N2B C1B C10B C5B -55.7 . . . . ?
 N2B C1B C10B C9B 123.2 . . . . ?
 C1B N2B C11B O3B -42.8 . . . . ?
 C1B N2B C11B N3B 139.8 . . . . ?
 C1B C2B C3B O1B 108.6 . . . . ?
 C1B C2B C3B C4B -0.6 . . . . ?
 C2B O1B C3B C4B 99.4 . . . . ?
 C2B C1B C10B C5B 55.4 . . . . ?
 C2B C1B C10B C9B -125.7 . . . . ?
 C2B C3B C4B N1B -59.8 . . . . ?
 C2B C3B C4B C5B 54.5 . . . . ?
 C3B O1B C2B C1B -100.2 . . . . ?
 C3B C4B C5B C6B 126.5 . . . . ?
 C3B C4B C5B C10B -55.3 . . . . ?
 C4B N1B N2B C1B -1.0 . . . . ?
 C4B N1B N2B C11B 137.4 . . . . ?
 C4B N1B C12B O2B 44.0 . . . . ?
 C4B N1B C12B N3B -137.7 . . . . ?
 C4B C5B C6B Cl1B -2.1 . . . . ?
 C4B C5B C6B C7B 178.7 . . . . ?
 C4B C5B C10B C1B -0.3 . . . . ?
 C4B C5B C10B C9B -179.2 . . . . ?
 C5B C6B C7B C8B 0.1 . . . . ?
 C6B C5B C10B C1B 178.1 . . . . ?
 C6B C5B C10B C9B -0.7 . . . . ?
 C6B C7B C8B C9B -0.5 . . . . ?
 C7B C8B C9B C10B 0.3 . . . . ?
 C8B C9B C10B C1B -178.4 . . . . ?
 C8B C9B C10B C5B 0.3 . . . . ?
 C10B C1B C2B O1B 11.5 . . . . ?
 C10B C1B C2B C3B -53.8 . . . . ?
 C10B C5B C6B Cl1B 179.7 . . . . ?
 C10B C5B C6B C7B 0.5 . . . . ?
 C11B N2B C1B C2B 168.9 . . . . ?
 C11B N2B C1B C10B -74.9 . . . . ?
 C11B N3B C12B O2B -172.5 . . . . ?
 C11B N3B C12B N1B 9.2 . . . . ?
 C12B N1B N2B C1B -139.9 . . . . ?
 C12B N1B N2B C11B -1.5 . . . . ?
 C12B N1B C4B C3B -166.8 . . . . ?
 C12B N1B C4B C5B 77.0 . . . . ?
 C12B N3B C11B O3B 172.5 . . . . ?
 C12B N3B C11B N2B -10.2 . . . . ?
 C13B N3B C11B O3B -10.9 . . . . ?
 C13B N3B C11B N2B 166.4 . . . . ?
 C13B N3B C12B O2B 10.9 . . . . ?
 C13B N3B C12B N1B -167.4 . . . . ?

_olex2_date_sample_data_collection  2018-12-10
_olex2_date_sample_submission      2018-12-07
_olex2_exptl_crystal_mounting_method 
 'Mounted using Paratone-N oil on a Cryo-Loop with (0 3 2) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id  D03S
_olex2_submission_special_instructions  'No special instructions were received'
