data_boger95_0m_a
_audit_creation_date               2018-11-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
_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           'C19 H20 N4 O2'
_chemical_formula_sum              'C19 H20 N4 O2'
_chemical_formula_weight           336.39
_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                     13.3231(7)
_cell_length_b                     9.9116(6)
_cell_length_c                     14.2356(7)
_cell_angle_alpha                  90
_cell_angle_beta                   104.338(3)
_cell_angle_gamma                  90
_cell_volume                       1821.30(17)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2598
_cell_measurement_temperature      100
_cell_measurement_theta_max        25.389
_cell_measurement_theta_min        2.413
_shelx_estimated_absorpt_T_max     0.992
_shelx_estimated_absorpt_T_min     0.980
_exptl_absorpt_coefficient_mu      0.082
_exptl_absorpt_correction_T_max    0.7457
_exptl_absorpt_correction_T_min    0.6822
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0472 before and 0.0420 after correction. The Ratio of minimum to maximum transmission is 0.9148. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              yellow
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.227
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               712
_exptl_crystal_size_max            0.25
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0437
_diffrn_reflns_av_unetI/netI       0.0536
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         17
_diffrn_reflns_limit_h_min         -17
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              14723
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.301
_diffrn_reflns_theta_min           2.954
_diffrn_ambient_temperature        100.0
_diffrn_detector                   'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CCD Area Detector'
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device         'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         '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                     'sealed tube'
_diffrn_source_type                fine-focus
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3136
_reflns_number_total               4497
_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 V8.38A (?, 2016)'
_computing_data_collection         'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_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           0.334
_refine_diff_density_min           -0.341
_refine_diff_density_rms           0.048
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       229
_refine_ls_number_reflns           4497
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0793
_refine_ls_R_factor_gt             0.0474
_refine_ls_restrained_S_all        1.013
_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)+(0.0453P)²+0.4394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0984
_refine_ls_wR_factor_ref           0.1116
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C3(H3), C7(H7), C10(H10), C6(H6), C4(H4), C5(H5), C11(H11),
 C13(H13), C12(H12)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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
 O2 O 0.65556(8) 0.50308(10) 0.49217(7) 0.0182(2) Uani 1 1 d . . . . .
 O1 O 0.71864(8) 0.32535(10) 0.42263(7) 0.0195(2) Uani 1 1 d . . . . .
 N4 N 0.61717(9) 0.64578(12) 0.33762(8) 0.0153(3) Uani 1 1 d . . . . .
 N3 N 0.67012(9) 0.52061(12) 0.33951(8) 0.0156(3) Uani 1 1 d . . . . .
 N1 N 0.68218(9) 0.66875(12) 0.20099(8) 0.0162(3) Uani 1 1 d . . . . .
 H1 H 0.720222 0.719290 0.172484 0.019 Uiso 1 1 calc R . . . .
 N2 N 0.65704(9) 0.45022(12) 0.25004(8) 0.0155(3) Uani 1 1 d . . . . .
 C15 C 0.68245(11) 0.43882(14) 0.41980(10) 0.0152(3) Uani 1 1 d . . . . .
 C1 C 0.66735(10) 0.53120(14) 0.18244(10) 0.0142(3) Uani 1 1 d . . . . .
 C8 C 0.63194(11) 0.71977(14) 0.26825(10) 0.0149(3) Uani 1 1 d . . . . .
 C16 C 0.67067(12) 0.43865(16) 0.58896(10) 0.0200(3) Uani 1 1 d . . . . .
 C9 C 0.59424(11) 0.86066(14) 0.25822(11) 0.0172(3) Uani 1 1 d . . . . .
 C2 C 0.65319(10) 0.47920(15) 0.08288(10) 0.0155(3) Uani 1 1 d . . . . .
 C14 C 0.58163(11) 0.92938(15) 0.33997(11) 0.0221(3) Uani 1 1 d . . . . .
 H14 H 0.592367 0.883687 0.400304 0.026 Uiso 1 1 calc R . . . .
 C3 C 0.62797(12) 0.56482(15) 0.00267(10) 0.0202(3) Uani 1 1 d . . . . .
 H3 H 0.623514 0.659373 0.011774 0.024 Uiso 1 1 calc R . . . .
 C7 C 0.66067(11) 0.34059(15) 0.06823(10) 0.0185(3) Uani 1 1 d . . . . .
 H7 H 0.678196 0.281552 0.122403 0.022 Uiso 1 1 calc R . . . .
 C10 C 0.57629(11) 0.92843(15) 0.16955(11) 0.0217(3) Uani 1 1 d . . . . .
 H10 H 0.583669 0.881988 0.113268 0.026 Uiso 1 1 calc R . . . .
 C18 C 0.60836(13) 0.30882(17) 0.58157(11) 0.0263(4) Uani 1 1 d . . . . .
 H18A H 0.536333 0.326492 0.546927 0.039 Uiso 1 1 calc GR . . . .
 H18B H 0.610569 0.275325 0.646821 0.039 Uiso 1 1 calc GR . . . .
 H18C H 0.638031 0.240994 0.546199 0.039 Uiso 1 1 calc GR . . . .
 C6 C 0.64268(12) 0.28863(16) -0.02488(11) 0.0234(3) Uani 1 1 d . . . . .
 H6 H 0.648255 0.194300 -0.034280 0.028 Uiso 1 1 calc R . . . .
 C17 C 0.78546(12) 0.41633(17) 0.63308(11) 0.0270(4) Uani 1 1 d . . . . .
 H17A H 0.812289 0.350684 0.593935 0.041 Uiso 1 1 calc GR . . . .
 H17B H 0.795597 0.381926 0.699316 0.041 Uiso 1 1 calc GR . . . .
 H17C H 0.822553 0.501971 0.634469 0.041 Uiso 1 1 calc GR . . . .
 C4 C 0.60934(13) 0.51207(17) -0.09052(11) 0.0247(4) Uani 1 1 d . . . . .
 H4 H 0.591612 0.570753 -0.144886 0.030 Uiso 1 1 calc R . . . .
 C19 C 0.62772(15) 0.54635(17) 0.64433(11) 0.0312(4) Uani 1 1 d . . . . .
 H19A H 0.664033 0.631713 0.641663 0.047 Uiso 1 1 calc GR . . . .
 H19B H 0.637875 0.518363 0.712065 0.047 Uiso 1 1 calc GR . . . .
 H19C H 0.553576 0.558405 0.614953 0.047 Uiso 1 1 calc GR . . . .
 C5 C 0.61645(13) 0.37446(17) -0.10462(11) 0.0253(4) Uani 1 1 d . . . . .
 H5 H 0.603485 0.338809 -0.168450 0.030 Uiso 1 1 calc R . . . .
 C11 C 0.54771(12) 1.06341(16) 0.16348(13) 0.0288(4) Uani 1 1 d . . . . .
 H11 H 0.534982 1.108999 0.102979 0.035 Uiso 1 1 calc R . . . .
 C13 C 0.55338(12) 1.06468(16) 0.33328(13) 0.0292(4) Uani 1 1 d . . . . .
 H13 H 0.544781 1.111334 0.389058 0.035 Uiso 1 1 calc R . . . .
 C12 C 0.53775(13) 1.13160(16) 0.24546(14) 0.0323(4) Uani 1 1 d . . . . .
 H12 H 0.520129 1.224661 0.241498 0.039 Uiso 1 1 calc R . . . .


_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
 O2 C15 1.3335(16) . ?
 O2 C16 1.4865(17) . ?
 O1 C15 1.2204(17) . ?
 N4 N3 1.4241(16) . ?
 N4 C8 1.2837(18) . ?
 N3 N2 1.4246(15) . ?
 N3 C15 1.3776(17) . ?
 N1 H1 0.8800 . ?
 N1 C1 1.3934(18) . ?
 N1 C8 1.3921(17) . ?
 N2 C1 1.2864(18) . ?
 C1 C2 1.4756(19) . ?
 C8 C9 1.479(2) . ?
 C16 C18 1.521(2) . ?
 C16 C17 1.519(2) . ?
 C16 C19 1.520(2) . ?
 C9 C14 1.394(2) . ?
 C9 C10 1.397(2) . ?
 C2 C3 1.395(2) . ?
 C2 C7 1.397(2) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.390(2) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.390(2) . ?
 C7 H7 0.9500 . ?
 C7 C6 1.386(2) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.388(2) . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C6 H6 0.9500 . ?
 C6 C5 1.392(2) . ?
 C17 H17A 0.9800 . ?
 C17 H17B 0.9800 . ?
 C17 H17C 0.9800 . ?
 C4 H4 0.9500 . ?
 C4 C5 1.385(2) . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?
 C5 H5 0.9500 . ?
 C11 H11 0.9500 . ?
 C11 C12 1.383(3) . ?
 C13 H13 0.9500 . ?
 C13 C12 1.385(2) . ?
 C12 H12 0.9500 . ?

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
 C15 O2 C16 120.69(11) . . ?
 C8 N4 N3 110.04(11) . . ?
 N4 N3 N2 117.35(10) . . ?
 C15 N3 N4 119.01(11) . . ?
 C15 N3 N2 114.62(11) . . ?
 C1 N1 H1 122.7 . . ?
 C8 N1 H1 122.7 . . ?
 C8 N1 C1 114.59(11) . . ?
 C1 N2 N3 110.56(11) . . ?
 O2 C15 N3 111.12(12) . . ?
 O1 C15 O2 126.45(13) . . ?
 O1 C15 N3 122.32(12) . . ?
 N1 C1 C2 120.15(12) . . ?
 N2 C1 N1 120.34(12) . . ?
 N2 C1 C2 119.25(13) . . ?
 N4 C8 N1 120.86(13) . . ?
 N4 C8 C9 120.04(13) . . ?
 N1 C8 C9 119.09(12) . . ?
 O2 C16 C18 110.67(12) . . ?
 O2 C16 C17 109.71(12) . . ?
 O2 C16 C19 101.36(12) . . ?
 C17 C16 C18 112.45(13) . . ?
 C17 C16 C19 110.95(14) . . ?
 C19 C16 C18 111.16(13) . . ?
 C14 C9 C8 119.28(13) . . ?
 C14 C9 C10 119.35(14) . . ?
 C10 C9 C8 121.28(13) . . ?
 C3 C2 C1 121.41(13) . . ?
 C3 C2 C7 119.18(13) . . ?
 C7 C2 C1 119.34(13) . . ?
 C9 C14 H14 120.0 . . ?
 C13 C14 C9 120.06(15) . . ?
 C13 C14 H14 120.0 . . ?
 C2 C3 H3 119.9 . . ?
 C4 C3 C2 120.15(14) . . ?
 C4 C3 H3 119.9 . . ?
 C2 C7 H7 119.8 . . ?
 C6 C7 C2 120.41(14) . . ?
 C6 C7 H7 119.8 . . ?
 C9 C10 H10 119.9 . . ?
 C11 C10 C9 120.17(15) . . ?
 C11 C10 H10 119.9 . . ?
 C16 C18 H18A 109.5 . . ?
 C16 C18 H18B 109.5 . . ?
 C16 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 C7 C6 H6 119.9 . . ?
 C7 C6 C5 120.11(14) . . ?
 C5 C6 H6 119.9 . . ?
 C16 C17 H17A 109.5 . . ?
 C16 C17 H17B 109.5 . . ?
 C16 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 C3 C4 H4 119.8 . . ?
 C5 C4 C3 120.41(14) . . ?
 C5 C4 H4 119.8 . . ?
 C16 C19 H19A 109.5 . . ?
 C16 C19 H19B 109.5 . . ?
 C16 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 C6 C5 H5 120.1 . . ?
 C4 C5 C6 119.73(14) . . ?
 C4 C5 H5 120.1 . . ?
 C10 C11 H11 120.0 . . ?
 C12 C11 C10 120.05(16) . . ?
 C12 C11 H11 120.0 . . ?
 C14 C13 H13 119.9 . . ?
 C12 C13 C14 120.11(16) . . ?
 C12 C13 H13 119.9 . . ?
 C11 C12 C13 120.22(15) . . ?
 C11 C12 H12 119.9 . . ?
 C13 C12 H12 119.9 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
