 
data_DLTrp
#data_eh80trp
# Linda JW Shimon, WIS,  measured in Wroclaw Demo
# Kai Tao Ehud Gazit, TAU
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C11 H12 N2 O2' 
_chemical_formula_sum
 'C11 H12 N2 O2' 
_chemical_formula_weight          204.23

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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.
;
 
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                    18.8828(3)
_cell_length_b                    5.75690(10)
_cell_length_c                    9.30540(10)
_cell_angle_alpha                 90
_cell_angle_beta                  101.737(2)
_cell_angle_gamma                 90
_cell_volume                      990.41(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used   12508
_cell_measurement_theta_min     4.7720
_cell_measurement_theta_max     79.0830
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.370          
_exptl_crystal_F_000              432
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.312
_exptl_crystal_size_mid           0.239
_exptl_crystal_size_min           0.170
_exptl_absorpt_coefficient_mu     0.788
_shelx_estimated_absorpt_T_min    0.791
_shelx_estimated_absorpt_T_max    0.878
_exptl_absorpt_correction_T_min                   0.77652
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44t (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min           0.676
_oxdiff_exptl_absorpt_empirical_full_max           1.374
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             20526
_diffrn_reflns_av_unetI/netI      0.0145
_diffrn_reflns_av_R_equivalents   0.0336
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          4.784
_diffrn_reflns_theta_max          79.323
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.993
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              2132
_reflns_number_gt                 2014
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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.
;
 
_computing_data_collection        'CrysAlisPro 1.171.39.44t (Rigaku OD, 2018)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.44t (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.44t (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0424P)²+0.6646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2132
_refine_ls_number_parameters      137
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0410
_refine_ls_R_factor_gt            0.0393
_refine_ls_wR_factor_ref          0.0979
_refine_ls_wR_factor_gt           0.0969
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_restrained_S_all       1.042
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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 0.48012(4) 0.33718(15) 0.63137(9) 0.0178(2) Uani 1 1 d . . . . .
O2 O 0.37492(5) 0.19552(16) 0.50730(11) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.43833(5) 0.77790(17) 0.57993(11) 0.0163(2) Uani 1 1 d . . . . .
H1A H 0.468213 0.750867 0.516376 0.020 Uiso 1 1 calc R U . . .
H1B H 0.464218 0.771730 0.673702 0.020 Uiso 1 1 calc R U . . .
H1C H 0.417930 0.920980 0.562296 0.020 Uiso 1 1 calc R U . . .
N2 N 0.17969(6) 0.2269(2) 0.65554(12) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.158303 0.104941 0.684736 0.028 Uiso 1 1 calc R U . . .
C1 C 0.38040(6) 0.5979(2) 0.55931(13) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.348904 0.618866 0.459912 0.019 Uiso 1 1 calc R U . . .
C2 C 0.41463(6) 0.3560(2) 0.56686(12) 0.0159(2) Uani 1 1 d . . . . .
C3 C 0.33373(6) 0.6303(2) 0.67575(13) 0.0185(3) Uani 1 1 d . . . . .
H3A H 0.362181 0.582024 0.772529 0.022 Uiso 1 1 calc R U . . .
H3B H 0.322178 0.797291 0.682040 0.022 Uiso 1 1 calc R U . . .
C4 C 0.26462(7) 0.4950(2) 0.64398(13) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.20210(7) 0.5446(2) 0.53115(13) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.18442(7) 0.7202(2) 0.42583(15) 0.0224(3) Uani 1 1 d . . . . .
H6 H 0.218541 0.837670 0.416537 0.027 Uiso 1 1 calc R U . . .
C7 C 0.11645(8) 0.7200(3) 0.33552(15) 0.0268(3) Uani 1 1 d . . . . .
H7 H 0.104053 0.838515 0.263780 0.032 Uiso 1 1 calc R U . . .
C8 C 0.06534(7) 0.5470(3) 0.34813(15) 0.0277(3) Uani 1 1 d . . . . .
H8 H 0.019053 0.551256 0.284775 0.033 Uiso 1 1 calc R U . . .
C9 C 0.08117(7) 0.3707(3) 0.45103(15) 0.0252(3) Uani 1 1 d . . . . .
H9 H 0.046715 0.253880 0.459391 0.030 Uiso 1 1 calc R U . . .
C10 C 0.14980(7) 0.3719(2) 0.54193(14) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.24820(7) 0.3025(2) 0.71622(14) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.279618 0.231143 0.796840 0.026 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 C2 1.2646(14) . ?
O2 C2 1.2465(15) . ?
N1 C1 1.4904(15) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 C11 1.3728(17) . ?
N2 C10 1.3748(17) . ?
N2 H2 0.8800 . ?
C1 C2 1.5312(16) . ?
C1 C3 1.5408(16) . ?
C1 H1 1.0000 . ?
C3 C4 1.4969(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.3639(18) . ?
C4 C5 1.4399(17) . ?
C5 C6 1.4006(18) . ?
C5 C10 1.4191(18) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3962(18) . ?
C9 H9 0.9500 . ?
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
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 C10 109.20(11) . . ?
C11 N2 H2 125.4 . . ?
C10 N2 H2 125.4 . . ?
N1 C1 C2 109.55(9) . . ?
N1 C1 C3 109.58(9) . . ?
C2 C1 C3 111.98(10) . . ?
N1 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C3 C1 H1 108.6 . . ?
O2 C2 O1 126.12(11) . . ?
O2 C2 C1 116.33(10) . . ?
O1 C2 C1 117.55(10) . . ?
C4 C3 C1 113.48(10) . . ?
C4 C3 H3A 108.9 . . ?
C1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C11 C4 C5 106.59(11) . . ?
C11 C4 C3 127.01(12) . . ?
C5 C4 C3 126.39(11) . . ?
C6 C5 C10 119.02(12) . . ?
C6 C5 C4 134.17(12) . . ?
C10 C5 C4 106.78(11) . . ?
C7 C6 C5 118.94(12) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.12(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.36(13) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 117.29(13) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
N2 C10 C9 130.42(12) . . ?
N2 C10 C5 107.28(11) . . ?
C9 C10 C5 122.27(12) . . ?
C4 C11 N2 110.16(11) . . ?
C4 C11 H11 124.9 . . ?
N2 C11 H11 124.9 . . ?
 
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
N1 C1 C2 O2 -158.05(10) . . . . ?
C3 C1 C2 O2 80.15(13) . . . . ?
N1 C1 C2 O1 21.47(14) . . . . ?
C3 C1 C2 O1 -100.33(12) . . . . ?
N1 C1 C3 C4 166.79(10) . . . . ?
C2 C1 C3 C4 -71.43(13) . . . . ?
C1 C3 C4 C11 108.17(14) . . . . ?
C1 C3 C4 C5 -72.37(15) . . . . ?
C11 C4 C5 C6 177.41(14) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
C11 C4 C5 C10 -0.30(14) . . . . ?
C3 C4 C5 C10 -179.86(11) . . . . ?
C10 C5 C6 C7 0.03(18) . . . . ?
C4 C5 C6 C7 -177.47(13) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C11 N2 C10 C9 -177.65(13) . . . . ?
C11 N2 C10 C5 0.23(14) . . . . ?
C8 C9 C10 N2 177.51(13) . . . . ?
C8 C9 C10 C5 -0.08(19) . . . . ?
C6 C5 C10 N2 -178.08(11) . . . . ?
C4 C5 C10 N2 0.05(14) . . . . ?
C6 C5 C10 C9 0.01(19) . . . . ?
C4 C5 C10 C9 178.13(12) . . . . ?
C5 C4 C11 N2 0.45(14) . . . . ?
C3 C4 C11 N2 -179.99(12) . . . . ?
C10 N2 C11 C4 -0.44(15) . . . . ?
 
_refine_diff_density_max    0.334
_refine_diff_density_min   -0.232
_refine_diff_density_rms    0.045



