data_ng
_audit_creation_date               2019-08-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number             2013-2
_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. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety           'C6 N14 O4, 2(C H7 N4)'
_chemical_formula_sum              'C8 H14 N22 O4'
_chemical_formula_weight           482.41
_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/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                     7.9219(9)
_cell_length_b                     10.2466(12)
_cell_length_c                     11.8205(14)
_cell_angle_alpha                  90
_cell_angle_beta                   97.146(3)
_cell_angle_gamma                  90
_cell_volume                       952.05(19)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      1503
_cell_measurement_temperature      173
_cell_measurement_theta_max        24.12
_cell_measurement_theta_min        2.64
_shelx_estimated_absorpt_T_max     0.973
_shelx_estimated_absorpt_T_min     0.959
_exptl_absorpt_coefficient_mu      0.139
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6877
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0697 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.9223. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.683
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      ?
_exptl_crystal_description         cube
_exptl_crystal_F_000               496
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.3
_exptl_crystal_size_mid            0.2
_exptl_crystal_size_min            0.2
_exptl_special_details
;
 ?
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0384
_diffrn_reflns_av_unetI/netI       0.0414
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              7650
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.492
_diffrn_reflns_theta_min           2.591
_diffrn_ambient_temperature        173
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_special_details            ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1687
_reflns_number_total               2176
_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 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.263
_refine_diff_density_min           -0.298
_refine_diff_density_rms           0.065
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.089
_refine_ls_hydrogen_treatment      refall
_refine_ls_matrix_type             full
_refine_ls_number_parameters       182
_refine_ls_number_reflns           2176
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0576
_refine_ls_R_factor_gt             0.0432
_refine_ls_restrained_S_all        1.089
_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)+(0.0582P)²+0.1517P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1081
_refine_ls_wR_factor_ref           0.1197
_refine_special_details
;
 ?
;
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens     difmap
_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 0.2027(2) 0.40158(14) 0.26458(11) 0.0384(4) Uani 1 1 d . . . . .
 O2 O 0.43686(18) 0.41013(15) 0.38200(12) 0.0399(4) Uani 1 1 d . . . . .
 N5 N 0.12127(18) 0.44921(14) 0.62135(11) 0.0212(3) Uani 1 1 d . . . . .
 N6 N 0.24382(19) 0.41655(14) 0.55586(12) 0.0235(3) Uani 1 1 d . . . . .
 N1 N 0.29079(19) 0.41418(14) 0.80126(12) 0.0243(3) Uani 1 1 d . . . . .
 N7 N 0.2823(2) 0.41830(14) 0.35932(13) 0.0269(4) Uani 1 1 d . . . . .
 N3 N 0.0869(2) 0.35110(16) 0.89659(13) 0.0282(4) Uani 1 1 d . . . . .
 N9 N 0.5541(2) 0.32028(15) 1.06156(13) 0.0257(4) Uani 1 1 d . . . . .
 N11 N 0.8430(2) 0.30124(17) 1.06095(14) 0.0296(4) Uani 1 1 d . . . . .
 N2 N 0.2512(2) 0.37308(15) 0.90284(12) 0.0268(4) Uani 1 1 d . . . . .
 N4 N 0.01243(19) 0.37604(15) 0.79018(13) 0.0274(4) Uani 1 1 d . . . . .
 N10 N 0.6738(2) 0.38256(17) 0.90383(14) 0.0311(4) Uani 1 1 d . . . . .
 N8 N 0.5723(2) 0.2597(2) 1.16854(14) 0.0324(4) Uani 1 1 d . . . . .
 C2 C -0.0177(2) 0.50050(16) 0.55570(13) 0.0202(4) Uani 1 1 d . . . . .
 C00F C 0.6904(2) 0.33387(17) 1.00830(14) 0.0230(4) Uani 1 1 d . . . . .
 C1 C 0.1826(2) 0.44758(16) 0.45003(14) 0.0216(4) Uani 1 1 d . . . . .
 C3 C 0.1417(2) 0.41480(16) 0.73731(14) 0.0206(4) Uani 1 1 d . . . . .
 H H 0.761(3) 0.394(2) 0.8658(19) 0.035(6) Uiso 1 1 d . . . . .
 HA H 0.571(3) 0.398(2) 0.8704(18) 0.031(6) Uiso 1 1 d . . . . .
 HB H 0.944(3) 0.320(2) 1.0219(18) 0.039(6) Uiso 1 1 d . . . . .
 HC H 0.851(3) 0.263(3) 1.131(2) 0.058(8) Uiso 1 1 d . . . . .
 HD H 0.492(4) 0.198(3) 1.165(2) 0.067(9) Uiso 1 1 d . . . . .
 HE H 0.459(3) 0.334(2) 1.0246(19) 0.035(6) Uiso 1 1 d . . . . .
 HF H 0.546(3) 0.321(2) 1.219(2) 0.040(6) Uiso 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
 O1 N7 1.227(2) . ?
 O2 N7 1.223(2) . ?
 N5 N6 1.3568(19) . ?
 N5 C2 1.370(2) . ?
 N5 C3 1.405(2) . ?
 N6 C1 1.323(2) . ?
 N1 N2 1.346(2) . ?
 N1 C3 1.321(2) . ?
 N7 C1 1.440(2) . ?
 N3 N2 1.314(2) . ?
 N3 N4 1.346(2) . ?
 N9 N8 1.400(2) . ?
 N9 C00F 1.323(2) . ?
 N9 HE 0.83(2) . ?
 N11 C00F 1.332(2) . ?
 N11 HB 0.99(2) . ?
 N11 HC 0.91(3) . ?
 N4 C3 1.325(2) . ?
 N10 C00F 1.323(2) . ?
 N10 H 0.88(2) . ?
 N10 HA 0.87(2) . ?
 N8 HD 0.89(3) . ?
 N8 HF 0.91(2) . ?
 C2 C2 1.380(3) 3_566 ?
 C2 C1 1.404(2) 3_566 ?
 C1 C2 1.404(2) 3_566 ?

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
 N6 N5 C2 110.67(13) . . ?
 N6 N5 C3 119.42(14) . . ?
 C2 N5 C3 129.45(14) . . ?
 C1 N6 N5 106.04(14) . . ?
 C3 N1 N2 102.78(14) . . ?
 O1 N7 C1 116.23(16) . . ?
 O2 N7 O1 125.23(16) . . ?
 O2 N7 C1 118.53(15) . . ?
 N2 N3 N4 109.65(14) . . ?
 N8 N9 HE 122.3(15) . . ?
 C00F N9 N8 118.59(16) . . ?
 C00F N9 HE 118.0(15) . . ?
 C00F N11 HB 118.1(13) . . ?
 C00F N11 HC 119.2(16) . . ?
 HB N11 HC 123(2) . . ?
 N3 N2 N1 110.03(14) . . ?
 C3 N4 N3 102.89(14) . . ?
 C00F N10 H 122.4(15) . . ?
 C00F N10 HA 117.9(14) . . ?
 H N10 HA 120(2) . . ?
 N9 N8 HD 106.0(18) . . ?
 N9 N8 HF 106.5(15) . . ?
 HD N8 HF 108(2) . . ?
 N5 C2 C2 107.05(19) . 3_566 ?
 N5 C2 C1 148.16(15) . 3_566 ?
 C2 C2 C1 104.77(18) 3_566 3_566 ?
 N9 C00F N11 119.88(16) . . ?
 N9 C00F N10 119.46(17) . . ?
 N10 C00F N11 120.64(17) . . ?
 N6 C1 N7 118.92(15) . . ?
 N6 C1 C2 111.47(14) . 3_566 ?
 C2 C1 N7 129.48(15) 3_566 . ?
 N1 C3 N5 123.06(15) . . ?
 N1 C3 N4 114.66(15) . . ?
 N4 C3 N5 122.25(15) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
