data_cxy3080_0m
_audit_creation_date               2020-10-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_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. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C10 H9 N O3'
_chemical_formula_sum              'C10 H9 N O3'
_chemical_formula_weight           191.18
_chemical_absolute_configuration   ad
_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' 0.0181 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+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'

_cell_length_a                     5.0555(2)
_cell_length_b                     8.7313(4)
_cell_length_c                     19.4510(10)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       858.59(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7624
_cell_measurement_temperature      100
_cell_measurement_theta_max        71.90
_cell_measurement_theta_min        2.27
_shelx_estimated_absorpt_T_max     0.844
_shelx_estimated_absorpt_T_min     0.756
_exptl_absorpt_coefficient_mu      0.927
_exptl_absorpt_correction_T_max    0.7535
_exptl_absorpt_correction_T_min    0.6470
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1092 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.8587.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.479
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               400
_exptl_crystal_size_max            0.32
_exptl_crystal_size_mid            0.21
_exptl_crystal_size_min            0.19
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0308
_diffrn_reflns_av_unetI/netI       0.0206
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -6
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         23
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              8866
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           71.893
_diffrn_reflns_theta_min           5.554
_diffrn_ambient_temperature        100
_diffrn_detector                   'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CMOS area detector'
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker D8 VENTURE'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'microfocus sealed X-ray tube'
_diffrn_source_current             1.11
_diffrn_source_power               0.0555
_diffrn_source_type                'Incoatec I\ms'
_diffrn_source_voltage             50.0
_diffrn_special_details            ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.653
_reflns_Friedel_fraction_full      0.997
_reflns_Friedel_fraction_max       0.996
_reflns_number_gt                  1667
_reflns_number_total               1686
_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 V8.40A (Bruker, 2019)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.251
_refine_diff_density_min           -0.190
_refine_diff_density_rms           0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.02(5)
_refine_ls_extinction_coef         0.0081(15)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       129
_refine_ls_number_reflns           1686
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0259
_refine_ls_R_factor_gt             0.0255
_refine_ls_restrained_S_all        1.075
_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)+(0.0350P)²+0.2276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0663
_refine_ls_wR_factor_ref           0.0666
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), N1(H1), C10(H10), C11(H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.1948(2) 0.52862(13) 0.54165(6) 0.0175(3) Uani 1 1 d . . . . .
 O2 O 0.2921(2) 0.76750(13) 0.43982(6) 0.0148(3) Uani 1 1 d . . . . .
 H2 H 0.423556 0.821228 0.450594 0.022 Uiso 1 1 calc R U . . .
 O3 O 0.9104(2) 0.35015(13) 0.42425(6) 0.0148(3) Uani 1 1 d . . . . .
 C1 C 0.3530(3) 0.51811(19) 0.49502(8) 0.0132(4) Uani 1 1 d . . . . .
 C2 C 0.3724(3) 0.61542(18) 0.43025(8) 0.0127(3) Uani 1 1 d . . . . .
 H2A H 0.250043 0.569205 0.395587 0.015 Uiso 1 1 calc R U . . .
 C3 C 0.6569(3) 0.58625(19) 0.40469(8) 0.0122(3) Uani 1 1 d . . . . .
 H3 H 0.774110 0.666513 0.425114 0.015 Uiso 1 1 calc R U . . .
 C4 C 0.6985(3) 0.58685(18) 0.32759(8) 0.0128(3) Uani 1 1 d . . . . .
 C5 C 0.5471(4) 0.49293(19) 0.28522(9) 0.0178(4) Uani 1 1 d . . . . .
 H5 H 0.415321 0.428595 0.304663 0.021 Uiso 1 1 calc R U . . .
 C6 C 0.5881(4) 0.4929(2) 0.21448(9) 0.0219(4) Uani 1 1 d . . . . .
 H6 H 0.483087 0.429429 0.185711 0.026 Uiso 1 1 calc R U . . .
 C7 C 0.7821(4) 0.5855(2) 0.18590(9) 0.0225(4) Uani 1 1 d . . . . .
 H7 H 0.811964 0.584171 0.137679 0.027 Uiso 1 1 calc R U . . .
 C8 C 0.7247(3) 0.43311(18) 0.43857(8) 0.0124(3) Uani 1 1 d . . . . .
 N1 N 0.5443(3) 0.40624(16) 0.49025(7) 0.0138(3) Uani 1 1 d . . . . .
 H1 H 0.550615 0.325791 0.517459 0.017 Uiso 1 1 calc R U . . .
 C10 C 0.9325(4) 0.6799(2) 0.22783(9) 0.0210(4) Uani 1 1 d . . . . .
 H10 H 1.064754 0.743753 0.208281 0.025 Uiso 1 1 calc R U . . .
 C11 C 0.8899(4) 0.68136(19) 0.29841(9) 0.0164(4) Uani 1 1 d . . . . .
 H11 H 0.991833 0.747133 0.326900 0.020 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 1.213(2) . ?
 O2 H2 0.8400 . ?
 O2 C2 1.4009(19) . ?
 O3 C8 1.218(2) . ?
 C1 C2 1.523(2) . ?
 C1 N1 1.378(2) . ?
 C2 H2A 1.0000 . ?
 C2 C3 1.543(2) . ?
 C3 H3 1.0000 . ?
 C3 C4 1.514(2) . ?
 C3 C8 1.530(2) . ?
 C4 C5 1.392(2) . ?
 C4 C11 1.393(2) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.391(2) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.387(3) . ?
 C7 H7 0.9500 . ?
 C7 C10 1.387(3) . ?
 C8 N1 1.378(2) . ?
 N1 H1 0.8800 . ?
 C10 H10 0.9500 . ?
 C10 C11 1.390(3) . ?
 C11 H11 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
 C2 O2 H2 109.5 . . ?
 O1 C1 C2 128.24(15) . . ?
 O1 C1 N1 124.54(15) . . ?
 N1 C1 C2 107.14(13) . . ?
 O2 C2 C1 113.59(13) . . ?
 O2 C2 H2A 107.0 . . ?
 O2 C2 C3 118.00(13) . . ?
 C1 C2 H2A 107.0 . . ?
 C1 C2 C3 103.55(13) . . ?
 C3 C2 H2A 107.0 . . ?
 C2 C3 H3 108.0 . . ?
 C4 C3 C2 116.60(13) . . ?
 C4 C3 H3 108.0 . . ?
 C4 C3 C8 113.49(13) . . ?
 C8 C3 C2 102.39(13) . . ?
 C8 C3 H3 108.0 . . ?
 C5 C4 C3 120.54(15) . . ?
 C5 C4 C11 119.33(15) . . ?
 C11 C4 C3 120.13(15) . . ?
 C4 C5 H5 119.9 . . ?
 C6 C5 C4 120.24(17) . . ?
 C6 C5 H5 119.9 . . ?
 C5 C6 H6 119.9 . . ?
 C7 C6 C5 120.11(17) . . ?
 C7 C6 H6 119.9 . . ?
 C6 C7 H7 120.1 . . ?
 C10 C7 C6 119.88(16) . . ?
 C10 C7 H7 120.1 . . ?
 O3 C8 C3 126.46(15) . . ?
 O3 C8 N1 125.16(15) . . ?
 N1 C8 C3 108.35(13) . . ?
 C1 N1 C8 113.15(13) . . ?
 C1 N1 H1 123.4 . . ?
 C8 N1 H1 123.4 . . ?
 C7 C10 H10 119.9 . . ?
 C7 C10 C11 120.10(17) . . ?
 C11 C10 H10 119.9 . . ?
 C4 C11 H11 119.8 . . ?
 C10 C11 C4 120.32(16) . . ?
 C10 C11 H11 119.8 . . ?

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 O2 32.1(2) . . . . ?
 O1 C1 C2 C3 161.28(17) . . . . ?
 O1 C1 N1 C8 -170.34(15) . . . . ?
 O2 C2 C3 C4 -86.98(18) . . . . ?
 O2 C2 C3 C8 148.53(14) . . . . ?
 O3 C8 N1 C1 -179.60(15) . . . . ?
 C1 C2 C3 C4 146.55(14) . . . . ?
 C1 C2 C3 C8 22.06(15) . . . . ?
 C2 C1 N1 C8 12.65(18) . . . . ?
 C2 C3 C4 C5 -54.1(2) . . . . ?
 C2 C3 C4 C11 126.17(17) . . . . ?
 C2 C3 C8 O3 166.17(15) . . . . ?
 C2 C3 C8 N1 -15.87(16) . . . . ?
 C3 C4 C5 C6 -179.36(17) . . . . ?
 C3 C4 C11 C10 178.65(16) . . . . ?
 C3 C8 N1 C1 2.40(18) . . . . ?
 C4 C3 C8 O3 39.6(2) . . . . ?
 C4 C3 C8 N1 -142.40(14) . . . . ?
 C4 C5 C6 C7 0.7(3) . . . . ?
 C5 C4 C11 C10 -1.1(3) . . . . ?
 C5 C6 C7 C10 -1.0(3) . . . . ?
 C6 C7 C10 C11 0.3(3) . . . . ?
 C7 C10 C11 C4 0.8(3) . . . . ?
 C8 C3 C4 C5 64.6(2) . . . . ?
 C8 C3 C4 C11 -115.19(17) . . . . ?
 N1 C1 C2 O2 -151.07(13) . . . . ?
 N1 C1 C2 C3 -21.86(16) . . . . ?
 C11 C4 C5 C6 0.4(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
