data_mo_ydg_lcf_11_0m_a
_audit_creation_date               2022-11-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2014/7'
_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          ?
_chemical_formula_moiety           'C10 H12 Br F N6 O3'
_chemical_formula_sum              'C11 H12 Br F N5 O3'
_chemical_formula_weight           361.17
_chemical_absolute_configuration   .
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 '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             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'

_cell_length_a                     7.5369(3)
_cell_length_b                     12.4354(7)
_cell_length_c                     14.8372(7)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1390.61(12)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6149
_cell_measurement_temperature      303(2)
_cell_measurement_theta_max        26.797
_cell_measurement_theta_min        2.745
_shelx_estimated_absorpt_T_max     0.680
_shelx_estimated_absorpt_T_min     0.458
_exptl_absorpt_coefficient_mu      2.986
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.5833
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0728 after correction.
The Ratio of minimum to maximum transmission is 0.7823.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.725
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               724
_exptl_crystal_size_max            0.31
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.14
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0596
_diffrn_reflns_av_unetI/netI       0.0453
_diffrn_reflns_Laue_measured_fraction_full  1.001
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -9
_diffrn_reflns_limit_k_max         16
_diffrn_reflns_limit_k_min         -16
_diffrn_reflns_limit_l_max         19
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              20341
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.505
_diffrn_reflns_theta_min           2.137
_diffrn_ambient_temperature        303.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.001
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             1.4
_diffrn_source_power               0.07
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.727
_reflns_Friedel_fraction_full      0.997
_reflns_Friedel_fraction_max       0.993
_reflns_number_gt                  2604
_reflns_number_total               3182
_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 V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.819
_refine_diff_density_min           -0.933
_refine_diff_density_rms           0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.011(6)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.947
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       192
_refine_ls_number_reflns           3182
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0529
_refine_ls_R_factor_gt             0.0382
_refine_ls_restrained_S_all        0.947
_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)+(0.0476P)²+1.1123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0887
_refine_ls_wR_factor_ref           0.0966
_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,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N13(H13A,H13B)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_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
 Br1 Br 0.73390(7) 0.51405(5) 0.78376(4) 0.0578(2) Uani 1 1 d . . . . .
 N2 N 0.1459(5) 0.2953(3) 0.7362(2) 0.0323(9) Uani 1 1 d . . . . .
 O2 O 0.2411(4) 0.4918(2) 0.62604(19) 0.0347(7) Uani 1 1 d . . . . .
 O3 O -0.0840(5) 0.3693(3) 0.6022(2) 0.0431(9) Uani 1 1 d . . . . .
 H3 H -0.0026 0.3483 0.6344 0.065 Uiso 1 1 calc R U . . .
 O4 O 0.2797(6) 0.3211(3) 0.4338(2) 0.0472(9) Uani 1 1 d . . . . .
 H4 H 0.3054 0.2573 0.4285 0.071 Uiso 1 1 calc R U . . .
 F5 F 0.5613(5) 0.4234(4) 0.5060(2) 0.0798(14) Uani 1 1 d . . . . .
 N6 N 0.5124(5) 0.3732(4) 0.8753(3) 0.0341(9) Uani 1 1 d . . . . .
 N7 N 0.0994(5) 0.2120(3) 0.8813(3) 0.0319(9) Uani 1 1 d . . . . .
 N1 N -0.0884(7) 0.1813(4) 0.7639(3) 0.0514(13) Uani 1 1 d . . . . .
 H1A H -0.1490 0.1405 0.7992 0.062 Uiso 1 1 calc R U . . .
 H1B H -0.1216 0.1903 0.7090 0.062 Uiso 1 1 calc R U . . .
 C2 C 0.0589(6) 0.2312(4) 0.7948(3) 0.0322(10) Uani 1 1 d . . . . .
 C3 C 0.2935(6) 0.3361(3) 0.7732(3) 0.0282(9) Uani 1 1 d . . . . .
 N4 N 0.4146(5) 0.4055(3) 0.7344(2) 0.0305(8) Uani 1 1 d . . . . .
 C5 C 0.4132(6) 0.4509(4) 0.6434(3) 0.0353(11) Uani 1 1 d . . . . .
 H5 H 0.4988 0.5101 0.6405 0.042 Uiso 1 1 calc R U . . .
 C1 C 0.1808(6) 0.4546(4) 0.5385(3) 0.0338(10) Uani 1 1 d . . . . .
 H1 H 0.2181 0.5055 0.4918 0.041 Uiso 1 1 calc R U . . .
 C7 C -0.0192(6) 0.4485(4) 0.5412(3) 0.0380(11) Uani 1 1 d . . . . .
 H7A H -0.0659 0.5182 0.5585 0.046 Uiso 1 1 calc R U . . .
 H7B H -0.0628 0.4324 0.4811 0.046 Uiso 1 1 calc R U . . .
 C8 C 0.2755(7) 0.3486(4) 0.5255(3) 0.0366(10) Uani 1 1 d . . . . .
 H8 H 0.2137 0.2922 0.5593 0.044 Uiso 1 1 calc R U . . .
 C9 C 0.4553(7) 0.3699(5) 0.5683(3) 0.0463(14) Uani 1 1 d . . . . .
 H9 H 0.5112 0.3042 0.5913 0.056 Uiso 1 1 calc R U . . .
 C10 C 0.5399(6) 0.4237(4) 0.8005(3) 0.0339(10) Uani 1 1 d . . . . .
 C11 C 0.3549(6) 0.3184(4) 0.8591(3) 0.0284(9) Uani 1 1 d . . . . .
 C12 C 0.2485(7) 0.2539(3) 0.9154(3) 0.0303(9) Uani 1 1 d . . . . .
 N13 N 0.2863(6) 0.2348(4) 1.0020(3) 0.0458(11) Uani 1 1 d . . . . .
 H13A H 0.2156 0.1966 1.0342 0.055 Uiso 1 1 calc R U . . .
 H13B H 0.3814 0.2609 1.0254 0.055 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
 Br1 C10 1.861(5) . ?
 N2 C2 1.349(6) . ?
 N2 C3 1.340(6) . ?
 O2 C5 1.417(6) . ?
 O2 C1 1.452(5) . ?
 O3 H3 0.8200 . ?
 O3 C7 1.425(6) . ?
 O4 H4 0.8200 . ?
 O4 C8 1.403(5) . ?
 F5 C9 1.393(7) . ?
 N6 C10 1.292(6) . ?
 N6 C11 1.390(6) . ?
 N7 C2 1.341(6) . ?
 N7 C12 1.338(6) . ?
 N1 H1A 0.8600 . ?
 N1 H1B 0.8600 . ?
 N1 C2 1.353(6) . ?
 C3 N4 1.382(5) . ?
 C3 C11 1.373(6) . ?
 N4 C5 1.465(5) . ?
 N4 C10 1.380(6) . ?
 C5 H5 0.9800 . ?
 C5 C9 1.535(7) . ?
 C1 H1 0.9800 . ?
 C1 C7 1.510(7) . ?
 C1 C8 1.512(7) . ?
 C7 H7A 0.9700 . ?
 C7 H7B 0.9700 . ?
 C8 H8 0.9800 . ?
 C8 C9 1.520(7) . ?
 C9 H9 0.9800 . ?
 C11 C12 1.408(6) . ?
 C12 N13 1.337(6) . ?
 N13 H13A 0.8600 . ?
 N13 H13B 0.8600 . ?

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
 C3 N2 C2 111.3(4) . . ?
 C5 O2 C1 109.6(3) . . ?
 C7 O3 H3 109.5 . . ?
 C8 O4 H4 109.5 . . ?
 C10 N6 C11 103.1(4) . . ?
 C12 N7 C2 119.0(4) . . ?
 H1A N1 H1B 120.0 . . ?
 C2 N1 H1A 120.0 . . ?
 C2 N1 H1B 120.0 . . ?
 N2 C2 N1 116.9(4) . . ?
 N7 C2 N2 127.7(4) . . ?
 N7 C2 N1 115.4(4) . . ?
 N2 C3 N4 127.8(4) . . ?
 N2 C3 C11 126.8(4) . . ?
 C11 C3 N4 105.3(4) . . ?
 C3 N4 C5 128.4(4) . . ?
 C10 N4 C3 105.0(3) . . ?
 C10 N4 C5 126.7(4) . . ?
 O2 C5 N4 108.2(4) . . ?
 O2 C5 H5 109.0 . . ?
 O2 C5 C9 107.1(4) . . ?
 N4 C5 H5 109.0 . . ?
 N4 C5 C9 114.4(4) . . ?
 C9 C5 H5 109.0 . . ?
 O2 C1 H1 109.7 . . ?
 O2 C1 C7 107.8(4) . . ?
 O2 C1 C8 104.1(4) . . ?
 C7 C1 H1 109.7 . . ?
 C7 C1 C8 115.5(4) . . ?
 C8 C1 H1 109.7 . . ?
 O3 C7 C1 113.2(4) . . ?
 O3 C7 H7A 108.9 . . ?
 O3 C7 H7B 108.9 . . ?
 C1 C7 H7A 108.9 . . ?
 C1 C7 H7B 108.9 . . ?
 H7A C7 H7B 107.8 . . ?
 O4 C8 C1 110.3(4) . . ?
 O4 C8 H8 109.5 . . ?
 O4 C8 C9 115.3(4) . . ?
 C1 C8 H8 109.5 . . ?
 C1 C8 C9 102.5(4) . . ?
 C9 C8 H8 109.5 . . ?
 F5 C9 C5 106.6(5) . . ?
 F5 C9 C8 108.5(4) . . ?
 F5 C9 H9 112.6 . . ?
 C5 C9 H9 112.6 . . ?
 C8 C9 C5 103.5(4) . . ?
 C8 C9 H9 112.6 . . ?
 N6 C10 Br1 122.3(3) . . ?
 N6 C10 N4 114.9(4) . . ?
 N4 C10 Br1 122.8(3) . . ?
 N6 C11 C12 131.5(4) . . ?
 C3 C11 N6 111.7(4) . . ?
 C3 C11 C12 116.7(4) . . ?
 N7 C12 C11 118.4(4) . . ?
 N13 C12 N7 118.3(4) . . ?
 N13 C12 C11 123.3(4) . . ?
 C12 N13 H13A 120.0 . . ?
 C12 N13 H13B 120.0 . . ?
 H13A N13 H13B 120.0 . . ?

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
 N2 C3 N4 C5 -0.6(8) . . . . ?
 N2 C3 N4 C10 179.3(4) . . . . ?
 N2 C3 C11 N6 180.0(4) . . . . ?
 N2 C3 C11 C12 -2.6(7) . . . . ?
 O2 C5 C9 F5 99.4(4) . . . . ?
 O2 C5 C9 C8 -14.9(5) . . . . ?
 O2 C1 C7 O3 -65.6(5) . . . . ?
 O2 C1 C8 O4 -159.8(4) . . . . ?
 O2 C1 C8 C9 -36.5(4) . . . . ?
 O4 C8 C9 F5 37.9(7) . . . . ?
 O4 C8 C9 C5 150.9(4) . . . . ?
 N6 C11 C12 N7 178.8(5) . . . . ?
 N6 C11 C12 N13 0.8(8) . . . . ?
 C2 N2 C3 N4 -179.3(5) . . . . ?
 C2 N2 C3 C11 -0.2(7) . . . . ?
 C2 N7 C12 C11 1.3(7) . . . . ?
 C2 N7 C12 N13 179.4(5) . . . . ?
 C3 N2 C2 N7 4.1(7) . . . . ?
 C3 N2 C2 N1 -177.1(5) . . . . ?
 C3 N4 C5 O2 47.9(6) . . . . ?
 C3 N4 C5 C9 -71.4(6) . . . . ?
 C3 N4 C10 Br1 -179.3(3) . . . . ?
 C3 N4 C10 N6 0.7(6) . . . . ?
 C3 C11 C12 N7 1.9(6) . . . . ?
 C3 C11 C12 N13 -176.1(5) . . . . ?
 N4 C3 C11 N6 -0.8(5) . . . . ?
 N4 C3 C11 C12 176.6(4) . . . . ?
 N4 C5 C9 F5 -140.7(4) . . . . ?
 N4 C5 C9 C8 105.0(5) . . . . ?
 C5 O2 C1 C7 151.6(4) . . . . ?
 C5 O2 C1 C8 28.4(5) . . . . ?
 C5 N4 C10 Br1 0.6(7) . . . . ?
 C5 N4 C10 N6 -179.4(4) . . . . ?
 C1 O2 C5 N4 -132.1(4) . . . . ?
 C1 O2 C5 C9 -8.3(5) . . . . ?
 C1 C8 C9 F5 -82.0(5) . . . . ?
 C1 C8 C9 C5 31.0(5) . . . . ?
 C7 C1 C8 O4 82.2(5) . . . . ?
 C7 C1 C8 C9 -154.4(4) . . . . ?
 C8 C1 C7 O3 50.3(6) . . . . ?
 C10 N6 C11 C3 1.2(5) . . . . ?
 C10 N6 C11 C12 -175.8(5) . . . . ?
 C10 N4 C5 O2 -132.0(5) . . . . ?
 C10 N4 C5 C9 108.7(5) . . . . ?
 C11 N6 C10 Br1 178.8(4) . . . . ?
 C11 N6 C10 N4 -1.2(6) . . . . ?
 C11 C3 N4 C5 -179.8(5) . . . . ?
 C11 C3 N4 C10 0.1(5) . . . . ?
 C12 N7 C2 N2 -4.7(8) . . . . ?
 C12 N7 C2 N1 176.4(5) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
