data_dm62w_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       '2014/7'
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. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic         
 (1aR*,2S*,8R*,8aS*)-5-methyl-1a,2,8,8a-tetrahydro-4H-2,8-ethenooxireno[2,3-d][1,2,4]triazolo[1,2-a]pyridazine-4,6(5H)-dione
_chemical_formula_moiety           'C9 H9 N3 O3'
_chemical_formula_sum              'C9 H9 N3 O3'
_chemical_formula_weight           207.19
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                     7.5594(7)
_cell_length_b                     15.3365(14)
_cell_length_c                     7.7117(7)
_cell_angle_alpha                  90
_cell_angle_beta                   98.206(2)
_cell_angle_gamma                  90
_cell_volume                       884.90(14)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      5557
_cell_measurement_temperature      296.15
_cell_measurement_theta_max        30.509
_cell_measurement_theta_min        2.981
_shelx_estimated_absorpt_T_max     0.965
_shelx_estimated_absorpt_T_min     0.939
_exptl_absorpt_coefficient_mu      0.120
_exptl_absorpt_correction_T_max    0.7461
_exptl_absorpt_correction_T_min    0.6925
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0417 before and 0.0349 after correction. The Ratio of minimum to maximum transmission is 0.9282. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.555
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               432
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 -2.00 1.00 2.00 0.0650
 2.00 -1.00 -2.00 0.1870
 0.00 1.00 -1.00 0.1610
 0.00 -1.00 1.00 0.1690
 1.00 1.00 1.00 0.1870
 0.00 -1.00 -1.00 0.1260
 1.00 0.00 -1.00 0.1520
 -1.00 0.00 1.00 0.0910
 -1.00 -2.00 0.00 0.2320
 0.00 -1.00 0.00 0.2080
 0.00 1.00 0.00 0.2360
 1.00 -1.00 0.00 0.3120
 1.00 3.00 1.00 0.2090
 0.00 2.00 -1.00 0.1750

_exptl_crystal_preparation         ?
_exptl_crystal_recrystallization_method  ?
_exptl_crystal_size_max            0.532
_exptl_crystal_size_mid            0.453
_exptl_crystal_size_min            0.302
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0190
_diffrn_reflns_av_unetI/netI       0.0151
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         21
_diffrn_reflns_limit_k_min         -21
_diffrn_reflns_limit_l_max         10
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              12250
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.538
_diffrn_reflns_theta_min           3.773
_diffrn_ambient_temperature        296.15
_diffrn_detector                   'Bruker APEXII CCD area detector'
_diffrn_detector_area_resol_mean   ?
_diffrn_detector_type              'CCD area detector'
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device         'kappa diffractometer'
_diffrn_measurement_device_type    Mo_ApexII
_diffrn_measurement_method         'profile data from φ and ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'fine-focus sealed X-ray tube'
_diffrn_source_current             30.0
_diffrn_source_power               1.5
_diffrn_source_target              Mo
_diffrn_source_type                'Siemens fine-focus sealed tube'
_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                  2347
_reflns_number_total               2701
_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 v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL  (Sheldrick, 2008)'
_computing_structure_solution      'XT (Sheldrick, 2015)'
_refine_diff_density_max           0.321
_refine_diff_density_min           -0.297
_refine_diff_density_rms           0.057
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       137
_refine_ls_number_reflns           2701
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0469
_refine_ls_R_factor_gt             0.0418
_refine_ls_restrained_S_all        1.036
_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)+(0.0821P)²+0.1637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1242
_refine_ls_wR_factor_ref           0.1306
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O -0.01522(12) 0.74201(6) 0.38706(15) 0.0459(3) Uani 1 1 d . . . . .
 O2 O 0.64635(10) 0.62479(6) 0.27244(13) 0.0395(2) Uani 1 1 d . . . . .
 O3 O 0.21773(12) 0.41382(5) 0.24780(13) 0.0396(2) Uani 1 1 d . . . . .
 N1 N 0.37206(11) 0.61972(5) 0.37540(11) 0.02482(19) Uani 1 1 d . . . . .
 N2 N 0.23816(11) 0.55272(5) 0.36955(11) 0.02493(19) Uani 1 1 d . . . . .
 N3 N 0.47271(12) 0.49954(6) 0.26294(12) 0.0274(2) Uani 1 1 d . . . . .
 C1 C 0.03260(16) 0.65605(8) 0.44810(17) 0.0363(3) Uani 1 1 d . . . . .
 H1 H -0.0041 0.6365 0.5586 0.044 Uiso 1 1 calc R U . . .
 C2 C 0.05525(13) 0.58813(7) 0.30845(15) 0.0297(2) Uani 1 1 d . . . . .
 H2 H -0.0366 0.5427 0.3017 0.036 Uiso 1 1 calc R U . . .
 C3 C 0.06052(15) 0.63108(8) 0.13455(16) 0.0352(2) Uani 1 1 d . . . . .
 H3 H -0.0155 0.6159 0.0334 0.042 Uiso 1 1 calc R U . . .
 C4 C 0.18441(15) 0.69305(8) 0.13893(16) 0.0345(2) Uani 1 1 d . . . . .
 H4 H 0.2028 0.7253 0.0410 0.041 Uiso 1 1 calc R U . . .
 C5 C 0.29166(13) 0.70599(6) 0.31642(15) 0.0292(2) Uani 1 1 d . . . . .
 H5 H 0.3827 0.7514 0.3154 0.035 Uiso 1 1 calc R U . . .
 C6 C 0.16855(16) 0.72396(7) 0.45355(17) 0.0365(3) Uani 1 1 d . . . . .
 H6 H 0.2198 0.7483 0.5672 0.044 Uiso 1 1 calc R U . . .
 C7 C 0.51271(13) 0.58639(7) 0.29807(13) 0.0261(2) Uani 1 1 d . . . . .
 C8 C 0.29921(14) 0.48070(6) 0.28647(13) 0.0261(2) Uani 1 1 d . . . . .
 C9 C 0.58980(17) 0.43924(8) 0.18910(17) 0.0395(3) Uani 1 1 d . . . . .
 H9A H 0.6509 0.4033 0.2806 0.059 Uiso 1 1 calc R U . . .
 H9B H 0.6757 0.4714 0.1344 0.059 Uiso 1 1 calc R U . . .
 H9C H 0.5202 0.4031 0.1034 0.059 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 C1 1.4288(14) . ?
 O1 C6 1.4374(15) . ?
 O2 C7 1.2098(13) . ?
 O3 C8 1.2116(13) . ?
 N1 N2 1.4386(11) . ?
 N1 C5 1.4993(13) . ?
 N1 C7 1.3886(13) . ?
 N2 C2 1.4976(13) . ?
 N2 C8 1.3885(13) . ?
 N3 C7 1.3839(13) . ?
 N3 C8 1.3801(13) . ?
 N3 C9 1.4516(14) . ?
 C1 H1 0.9800 . ?
 C1 C2 1.5254(16) . ?
 C1 C6 1.4595(17) . ?
 C2 H2 0.9800 . ?
 C2 C3 1.4997(16) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.3313(17) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.5011(16) . ?
 C5 H5 0.9800 . ?
 C5 C6 1.5301(15) . ?
 C6 H6 0.9800 . ?
 C9 H9A 0.9600 . ?
 C9 H9B 0.9600 . ?
 C9 H9C 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
 C1 O1 C6 61.22(8) . . ?
 N2 N1 C5 111.58(7) . . ?
 C7 N1 N2 107.58(8) . . ?
 C7 N1 C5 119.78(8) . . ?
 N1 N2 C2 111.40(7) . . ?
 C8 N2 N1 107.69(7) . . ?
 C8 N2 C2 119.74(8) . . ?
 C7 N3 C9 124.17(9) . . ?
 C8 N3 C7 111.16(8) . . ?
 C8 N3 C9 124.22(10) . . ?
 O1 C1 H1 118.6 . . ?
 O1 C1 C2 116.49(10) . . ?
 O1 C1 C6 59.68(8) . . ?
 C2 C1 H1 118.6 . . ?
 C6 C1 H1 118.6 . . ?
 C6 C1 C2 110.98(9) . . ?
 N2 C2 C1 102.54(9) . . ?
 N2 C2 H2 111.9 . . ?
 N2 C2 C3 107.42(8) . . ?
 C1 C2 H2 111.9 . . ?
 C3 C2 C1 110.57(9) . . ?
 C3 C2 H2 111.9 . . ?
 C2 C3 H3 123.2 . . ?
 C4 C3 C2 113.53(10) . . ?
 C4 C3 H3 123.2 . . ?
 C3 C4 H4 123.1 . . ?
 C3 C4 C5 113.83(10) . . ?
 C5 C4 H4 123.1 . . ?
 N1 C5 C4 107.62(9) . . ?
 N1 C5 H5 112.0 . . ?
 N1 C5 C6 102.09(8) . . ?
 C4 C5 H5 112.0 . . ?
 C4 C5 C6 110.57(9) . . ?
 C6 C5 H5 112.0 . . ?
 O1 C6 C1 59.10(8) . . ?
 O1 C6 C5 116.12(11) . . ?
 O1 C6 H6 119.0 . . ?
 C1 C6 C5 110.29(9) . . ?
 C1 C6 H6 119.0 . . ?
 C5 C6 H6 119.0 . . ?
 O2 C7 N1 126.82(10) . . ?
 O2 C7 N3 126.92(10) . . ?
 N3 C7 N1 106.21(8) . . ?
 O3 C8 N2 126.61(10) . . ?
 O3 C8 N3 127.17(10) . . ?
 N3 C8 N2 106.19(8) . . ?
 N3 C9 H9A 109.5 . . ?
 N3 C9 H9B 109.5 . . ?
 N3 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O1 C1 C2 N2 126.54(10) . . . . ?
 O1 C1 C2 C3 12.27(13) . . . . ?
 O1 C1 C6 C5 -109.01(11) . . . . ?
 N1 N2 C2 C1 -61.07(10) . . . . ?
 N1 N2 C2 C3 55.49(11) . . . . ?
 N1 N2 C8 O3 -175.00(10) . . . . ?
 N1 N2 C8 N3 7.12(10) . . . . ?
 N1 C5 C6 O1 -125.94(10) . . . . ?
 N1 C5 C6 C1 -61.31(12) . . . . ?
 N2 N1 C5 C4 -54.04(10) . . . . ?
 N2 N1 C5 C6 62.39(10) . . . . ?
 N2 N1 C7 O2 176.73(10) . . . . ?
 N2 N1 C7 N3 -5.68(10) . . . . ?
 N2 C2 C3 C4 -56.47(13) . . . . ?
 C1 O1 C6 C5 99.01(11) . . . . ?
 C1 C2 C3 C4 54.68(13) . . . . ?
 C2 N2 C8 O3 -46.44(15) . . . . ?
 C2 N2 C8 N3 135.67(9) . . . . ?
 C2 C1 C6 O1 109.22(11) . . . . ?
 C2 C1 C6 C5 0.20(14) . . . . ?
 C2 C3 C4 C5 0.20(15) . . . . ?
 C3 C4 C5 N1 55.70(12) . . . . ?
 C3 C4 C5 C6 -55.02(13) . . . . ?
 C4 C5 C6 O1 -11.67(13) . . . . ?
 C4 C5 C6 C1 52.96(13) . . . . ?
 C5 N1 N2 C2 -0.78(11) . . . . ?
 C5 N1 N2 C8 132.39(8) . . . . ?
 C5 N1 C7 O2 47.98(15) . . . . ?
 C5 N1 C7 N3 -134.43(9) . . . . ?
 C6 O1 C1 C2 -99.90(11) . . . . ?
 C6 C1 C2 N2 60.93(11) . . . . ?
 C6 C1 C2 C3 -53.34(13) . . . . ?
 C7 N1 N2 C2 -134.07(9) . . . . ?
 C7 N1 N2 C8 -0.89(10) . . . . ?
 C7 N1 C5 C4 72.87(11) . . . . ?
 C7 N1 C5 C6 -170.70(9) . . . . ?
 C7 N3 C8 O3 171.02(11) . . . . ?
 C7 N3 C8 N2 -11.11(11) . . . . ?
 C8 N2 C2 C1 172.08(9) . . . . ?
 C8 N2 C2 C3 -71.36(11) . . . . ?
 C8 N3 C7 O2 -171.86(11) . . . . ?
 C8 N3 C7 N1 10.55(11) . . . . ?
 C9 N3 C7 O2 0.63(17) . . . . ?
 C9 N3 C7 N1 -176.95(9) . . . . ?
 C9 N3 C8 O3 -1.47(17) . . . . ?
 C9 N3 C8 N2 176.40(10) . . . . ?

_olex2_date_sample_data_collection  2019-07-18
_olex2_date_sample_submission      2019-07-17
_olex2_exptl_crystal_mounting_method 
 'Mounted using Paratone-N oil on a Cryo-Loop with (2 2 1) face roughly perpendicular to the spindle axis'
_olex2_submission_original_sample_id  D62W
_olex2_submission_special_instructions  'No special instructions were received'
