data_xl-1-114_scale
_audit_creation_date               2020-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_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           'C11 H8 N2 O3'
_chemical_formula_sum              'C11 H8 N2 O3'
_chemical_formula_weight           216.19
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C11 H18 N2 O3'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 '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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     4.74660(10)
_cell_length_b                     12.1979(2)
_cell_length_c                     16.5531(3)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       958.40(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7139
_cell_measurement_temperature      150.01(10)
_cell_measurement_theta_max        73.7880
_cell_measurement_theta_min        4.4620
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.940
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.71685
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.498
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               448
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 3 -2 1 0.1960
 -3 1 1 0.1931
 0 -5 8 0.0216
 0 5 -8 0.0216
 0 -6 -7 0.0227
 0 6 7 0.0227
 0 1 11 0.0088
 0 -1 -11 0.0163

_exptl_crystal_recrystallization_method  ?
_exptl_crystal_size_max            0.411
_exptl_crystal_size_mid            0.063
_exptl_crystal_size_min            0.025
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 2.9965 -1.9602 1.0697 0.1705 0.9938 -0.0050
 -2.9971 0.9660 0.9327 -0.1862 -0.9402 0.2229
 -0.0013 -4.9764 8.0130 0.0361 0.2297 0.9480
 0.0013 4.9764 -8.0130 -0.0361 -0.2297 -0.9480
 0.0136 -6.0168 -6.9795 0.9976 -0.0422 -0.0349
 -0.0136 6.0168 6.9795 -0.9976 0.0422 0.0349
 -0.0112 1.0296 10.9937 -0.7315 0.1953 0.7004
 0.0112 -1.0296 -10.9937 0.7315 -0.1953 -0.7004

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0380
_diffrn_reflns_av_unetI/netI       0.0215
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         20
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              11478
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           74.091
_diffrn_reflns_theta_min           4.503
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        150.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   8.1297
_diffrn_detector_type              EosS2
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -32.00  56.00   1.00    2.50    --   37.20 -38.00 -30.00   88
  2  ω      1.00  76.00   1.00    2.50    --   37.20 -99.00  30.00   75
  3  ω    -30.00  54.00   1.00    2.50    --   37.20 -57.00  90.00   84
  4  ω     20.00 104.00   1.00    2.50    --   37.20  57.00-120.00   84
  5  ω      1.00  76.00   1.00    2.50    --   37.20 -99.00 120.00   75
  6  ω      1.00  76.00   1.00    2.50    --   37.20 -99.00-180.00   75
  7  ω     21.00 105.00   1.00    2.50    --   37.20  54.00  53.00   84
  8  ω     23.00  91.00   1.00    2.50    --   37.20-125.00 -60.00   68
  9  ω     20.00 104.00   1.00    2.50    --   37.20  57.00 -30.00   84
 10  ω    -32.00  56.00   1.00    2.50    --   37.20 -38.00 120.00   88
 11  ω     23.00  91.00   1.00    2.50    --   37.20-125.00 120.00   68
 12  ω     91.00 178.00   1.00   11.00    --  111.00  64.00 -60.00   87
 13  ω     41.00 116.00   1.00   11.00    --  111.00-111.00  90.00   75
 14  ω     57.00 150.00   1.00   11.00    --  111.00 178.00  30.00   93
 15  ω     41.00 116.00   1.00   11.00    --  111.00-111.00   0.00   75
 16  ω     44.00 131.00   1.00   11.00    --  111.00 -64.00  60.00   87
 17  ω     41.00 132.00   1.00   11.00    --  111.00 -30.00 125.92   91
 18  ω     41.00 157.00   1.00   11.00    --  111.00 -12.00 -90.00  116
 19  ω    105.00 131.00   1.00   11.00    --  111.00 -92.00  60.00   26
 20  ω     60.00  93.00   1.00   11.00    --  111.00 -77.00   0.00   33
 21  ω     95.00 124.00   1.00   11.00    --  111.00 -77.00   0.00   29
 22  ω     43.00  79.00   1.00   11.00    --  111.00 -92.00  60.00   36
 23  ω     50.00  87.00   1.00   11.00    --  111.00 -50.00 -30.00   37
 24  ω     66.00 124.00   1.00   11.00    --  111.00 -38.00  30.00   58
 25  ω     96.00 149.00   1.00   11.00    --  111.00 -15.00  23.38   53
 26  ω     45.00 131.00   1.00   11.00    --  111.00 -64.00-180.00   86
 27  ω     53.00  79.00   1.00   11.00    --  111.00-111.00 -90.00   26
 28  ω     49.00 109.00   1.00   11.00    --  111.00 -25.00 -60.00   60
 29  ω     98.00 124.00   1.00   11.00    --  111.00 -77.00 -60.00   26
 30  ω    140.00 166.00   1.00   11.00    --  111.00  38.00   0.00   26
 31  ω     83.00 112.00   1.00   11.00    --  111.00-111.00 -90.00   29
 32  ω     86.00 112.00   1.00   11.00    --  111.00-111.00 150.00   26
 33  ω     44.00  95.00   1.00   11.00    --  111.00 -50.00 -90.00   51
 34  ω     49.00  74.00   1.00   11.00    --  111.00 -77.00 -60.00   25
 35  ω     95.00 128.00   1.00   11.00    --  111.00  25.00-120.00   33
 36  ω     60.00  86.00   1.00   11.00    --  111.00 -25.00  60.00   26
 37  ω    106.00 132.00   1.00   11.00    --  111.00 -25.00  60.00   26
 38  ω     95.00 153.00   1.00   11.00    --  111.00  50.00-120.00   58
 39  ω     66.00  93.00   1.00   11.00    --  111.00 -15.00  23.38   27
 40  ω     84.00 115.00   1.00   11.00    --  111.00-111.00-150.00   31
 41  ω     95.00 121.00   1.00   11.00    --  111.00  50.00-150.00   26
 42  ω     93.00 172.00   1.00   11.00    --  111.00  38.00  90.00   79
 43  ω    120.00 146.00   1.00   11.00    --  111.00  25.00  90.00   26
 44  ω     86.00 112.00   1.00   11.00    --  111.00 -77.00-120.00   26
 45  ω     53.00 112.00   1.00   11.00    --  111.00-100.00-162.05   59
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0122995000
_diffrn_orient_matrix_UB_12        -0.0993924000
_diffrn_orient_matrix_UB_13        -0.0572203000
_diffrn_orient_matrix_UB_21        0.3149809000
_diffrn_orient_matrix_UB_22        -0.0148771000
_diffrn_orient_matrix_UB_23        0.0194802000
_diffrn_orient_matrix_UB_31        -0.0769862000
_diffrn_orient_matrix_UB_32        -0.0764925000
_diffrn_orient_matrix_UB_33        0.0707955000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.662
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.991
_reflns_number_gt                  1846
_reflns_number_total               1931
_reflns_odcompleteness_completeness  98.75
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       74.33
_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         'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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           0.232
_refine_diff_density_min           -0.224
_refine_diff_density_rms           0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.01(8)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       149
_refine_ls_number_reflns           1931
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0326
_refine_ls_R_factor_gt             0.0313
_refine_ls_restrained_S_all        1.063
_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)+(0.0614P)²+0.0229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0821
_refine_ls_wR_factor_ref           0.0831
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       ?
_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
 O6 O 1.1656(3) 0.44250(11) 0.31063(8) 0.0313(3) Uani 1 1 d . . . . .
 O8 O 0.8268(3) 0.49277(12) 0.22188(8) 0.0363(3) Uani 1 1 d . . . . .
 O16 O 0.8036(4) 0.68991(12) 0.34460(11) 0.0510(5) Uani 1 1 d . . . . .
 N9 N 0.6008(3) 0.34193(11) 0.43826(8) 0.0242(3) Uani 1 1 d . . . . .
 N12 N 0.2618(3) 0.38223(11) 0.54235(8) 0.0254(3) Uani 1 1 d . . . . .
 C1 C 0.9424(3) 0.36368(14) 0.31990(10) 0.0267(4) Uani 1 1 d . . . . .
 H1 H 1.012264 0.288960 0.328395 0.032 Uiso 1 1 calc R . . . .
 C2 C 0.7614(3) 0.40352(13) 0.38807(9) 0.0228(3) Uani 1 1 d . . . . .
 C3 C 0.7172(4) 0.51399(13) 0.40113(9) 0.0238(3) Uani 1 1 d . . . . .
 C4 C 0.8424(4) 0.59122(14) 0.34593(11) 0.0304(4) Uani 1 1 d . . . . .
 C5 C 1.0214(4) 0.53413(16) 0.28021(11) 0.0327(4) Uani 1 1 d . . . . .
 H5 H 1.152754 0.586048 0.255273 0.039 Uiso 1 1 calc R . . . .
 C7 C 0.7910(4) 0.37761(15) 0.23870(10) 0.0311(4) Uani 1 1 d . . . . .
 H7A H 0.877357 0.332821 0.197099 0.037 Uiso 1 1 calc R . . . .
 H7B H 0.593121 0.358580 0.243085 0.037 Uiso 1 1 calc R . . . .
 C10 C 0.4473(3) 0.41322(12) 0.48643(10) 0.0223(3) Uani 1 1 d . . . . .
 C11 C 0.5152(3) 0.52231(13) 0.46504(9) 0.0227(3) Uani 1 1 d . . . . .
 C13 C 0.1327(4) 0.46518(15) 0.58086(10) 0.0276(3) Uani 1 1 d . . . . .
 H13 H -0.000428 0.447839 0.620053 0.033 Uiso 1 1 calc R . . . .
 C14 C 0.1863(4) 0.57584(14) 0.56562(10) 0.0283(4) Uani 1 1 d . . . . .
 H14 H 0.091614 0.629470 0.594905 0.034 Uiso 1 1 calc R . . . .
 C15 C 0.3801(4) 0.60615(13) 0.50702(10) 0.0270(3) Uani 1 1 d . . . . .
 H15 H 0.418266 0.679470 0.496186 0.032 Uiso 1 1 calc R . . . .
 H9 H 0.630(5) 0.270(2) 0.4457(13) 0.032(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
 O6 C1 1.439(2) . ?
 O6 C5 1.404(2) . ?
 O8 C5 1.428(2) . ?
 O8 C7 1.442(2) . ?
 O16 C4 1.218(2) . ?
 N9 C2 1.355(2) . ?
 N9 C10 1.387(2) . ?
 N12 C10 1.332(2) . ?
 N12 C13 1.344(2) . ?
 C1 C2 1.499(2) . ?
 C1 C7 1.534(2) . ?
 C2 C3 1.381(2) . ?
 C3 C4 1.441(2) . ?
 C3 C11 1.431(2) . ?
 C4 C5 1.546(2) . ?
 C10 C11 1.414(2) . ?
 C11 C15 1.393(2) . ?
 C13 C14 1.397(2) . ?
 C14 C15 1.387(2) . ?

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
 C5 O6 C1 102.18(13) . . ?
 C5 O8 C7 106.84(13) . . ?
 C2 N9 C10 107.48(13) . . ?
 C10 N12 C13 114.67(14) . . ?
 O6 C1 C2 106.60(13) . . ?
 O6 C1 C7 100.23(14) . . ?
 C2 C1 C7 110.80(14) . . ?
 N9 C2 C1 127.17(14) . . ?
 N9 C2 C3 111.09(14) . . ?
 C3 C2 C1 121.41(15) . . ?
 C2 C3 C4 118.45(15) . . ?
 C2 C3 C11 106.65(14) . . ?
 C11 C3 C4 134.32(15) . . ?
 O16 C4 C3 126.55(17) . . ?
 O16 C4 C5 121.03(16) . . ?
 C3 C4 C5 112.24(14) . . ?
 O6 C5 O8 106.06(15) . . ?
 O6 C5 C4 111.97(14) . . ?
 O8 C5 C4 106.23(15) . . ?
 O8 C7 C1 102.82(14) . . ?
 N9 C10 C11 109.05(14) . . ?
 N12 C10 N9 124.67(14) . . ?
 N12 C10 C11 126.27(15) . . ?
 C10 C11 C3 105.72(13) . . ?
 C15 C11 C3 136.82(15) . . ?
 C15 C11 C10 117.45(15) . . ?
 N12 C13 C14 123.99(16) . . ?
 C15 C14 C13 120.31(15) . . ?
 C14 C15 C11 117.30(15) . . ?


_ins_header
;
TITL XL-1-114_scale in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   4.746577  12.197901  16.553098  90.0000  90.0000  90.0000
ZERR    3.00   0.000090   0.000219   0.000299   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H N O
UNIT 33.00 54.00 6.00 9.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  2.491
_oxdiff_exptl_absorpt_empirical_full_min  0.588
