
data_CJC1601

_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C16 H13 N3 O5'
_chemical_formula_sum
 'C16 H13 N3 O5'
_chemical_formula_weight          327.29

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            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'

_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'

_cell_length_a                    7.24510(14)
_cell_length_b                    9.38179(17)
_cell_length_c                    10.91846(19)
_cell_angle_alpha                 90
_cell_angle_beta                  90.4932(16)
_cell_angle_gamma                 90
_cell_volume                      742.12(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     6252
_cell_measurement_theta_min       4.0330
_cell_measurement_theta_max       73.2830

_exptl_crystal_description        'platy needles'
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.465
_exptl_crystal_F_000              340
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.31
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.03
_exptl_absorpt_coefficient_mu     0.939
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_correction_T_min   0.817
_exptl_absorpt_correction_T_max   0.975
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method        'omega scans'
_diffrn_detector_area_resol_mean  10.3745
_diffrn_reflns_number             11235
_diffrn_reflns_av_unetI/netI      0.0277
_diffrn_reflns_av_R_equivalents   0.0338
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          4.049
_diffrn_reflns_theta_max          73.852
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.976
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              2930
_reflns_number_gt                 2705
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.844
_reflns_Friedel_fraction_max      0.954
_reflns_Friedel_fraction_full     0.975

_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, Agilent Technologies'
_computing_cell_refinement        'CrysAlisPro, Agilent Technologies'
_computing_data_reduction         'CrysAlisPro, Agilent Technologies'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0336P)²+0.0874P] 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      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.0080(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Flack x determined using 1171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.09(10)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2930
_refine_ls_number_parameters      218
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0341
_refine_ls_R_factor_gt            0.0293
_refine_ls_wR_factor_ref          0.0727
_refine_ls_wR_factor_gt           0.0686
_refine_ls_goodness_of_fit_ref    1.093
_refine_ls_restrained_S_all       1.093
_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
N1 N 0.1520(3) 0.4081(2) 0.76630(16) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.1187(3) 0.3762(2) 0.89153(19) 0.0232(5) Uani 1 1 d . . . . .
O2 O 0.0678(2) 0.25798(18) 0.92113(15) 0.0310(4) Uani 1 1 d . . . . .
C3 C 0.1578(3) 0.4957(2) 0.97193(19) 0.0225(5) Uani 1 1 d . . . . .
C4 C 0.2311(3) 0.6211(2) 0.9347(2) 0.0234(4) Uani 1 1 d . . . . .
H4A H 0.2605 0.6945 0.9915 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2618(3) 0.6384(2) 0.8088(2) 0.0241(5) Uani 1 1 d . . . . .
C6 C 0.2186(3) 0.5336(2) 0.7279(2) 0.0239(5) Uani 1 1 d . . . . .
H6A H 0.2357 0.5493 0.6428 0.029 Uiso 1 1 calc R U . . .
N7 N 0.1190(3) 0.4795(2) 1.10266(17) 0.0254(4) Uani 1 1 d . . . . .
O8 O -0.0110(3) 0.4044(2) 1.13258(16) 0.0392(5) Uani 1 1 d . . . . .
O9 O 0.2169(3) 0.5445(2) 1.17519(15) 0.0350(4) Uani 1 1 d . . . . .
N10 N 0.3455(3) 0.7686(2) 0.76394(19) 0.0298(4) Uani 1 1 d . . . . .
O11 O 0.4190(3) 0.8477(2) 0.83860(17) 0.0397(4) Uani 1 1 d . . . . .
O12 O 0.3423(3) 0.7901(2) 0.65324(16) 0.0442(5) Uani 1 1 d . . . . .
C13 C 0.1183(3) 0.2867(3) 0.6788(2) 0.0276(5) Uani 1 1 d . . . . .
H13A H -0.0013 0.2410 0.7016 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2706(3) 0.1723(3) 0.6898(2) 0.0304(5) Uani 1 1 d . . . . .
H14A H 0.2853 0.1472 0.7774 0.036 Uiso 1 1 calc R U . . .
H14B H 0.2275 0.0857 0.6464 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4610(3) 0.2121(3) 0.6400(2) 0.0312(5) Uani 1 1 d . . . . .
H15A H 0.5424 0.1277 0.6477 0.037 Uiso 1 1 calc R U . . .
H15B H 0.4474 0.2333 0.5515 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5570(3) 0.3373(3) 0.7005(2) 0.0276(5) Uani 1 1 d . . . . .
C17 C 0.6338(4) 0.4450(3) 0.6297(2) 0.0343(6) Uani 1 1 d . . . . .
H17A H 0.6253 0.4394 0.5430 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7224(4) 0.5605(3) 0.6833(2) 0.0380(6) Uani 1 1 d . . . . .
H18A H 0.7745 0.6326 0.6332 0.046 Uiso 1 1 calc R U . . .
C19 C 0.7351(3) 0.5711(3) 0.8095(2) 0.0351(6) Uani 1 1 d . . . . .
H19A H 0.7948 0.6506 0.8464 0.042 Uiso 1 1 calc R U . . .
C20 C 0.6597(3) 0.4645(3) 0.8815(2) 0.0319(5) Uani 1 1 d . . . . .
H20A H 0.6682 0.4709 0.9682 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5721(3) 0.3488(3) 0.8280(2) 0.0280(5) Uani 1 1 d . . . . .
H21A H 0.5217 0.2764 0.8784 0.034 Uiso 1 1 calc R U . . .
C22 C 0.0985(3) 0.3416(3) 0.5537(2) 0.0331(5) Uani 1 1 d . . . . .
C23 C 0.0885(4) 0.3822(3) 0.4522(2) 0.0464(7) Uani 1 1 d . . . . .
H23A H 0.0805 0.4150 0.3700 0.056 Uiso 1 1 calc R U . . .

loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
N1 0.0235(9) 0.0241(9) 0.0223(9) -0.0028(7) 0.0011(7) 0.0012(8)
C2 0.0221(10) 0.0260(12) 0.0216(10) 0.0006(8) 0.0017(8) 0.0013(9)
O2 0.0390(9) 0.0249(9) 0.0293(8) -0.0001(7) 0.0067(7) -0.0067(7)
C3 0.0226(10) 0.0260(11) 0.0190(10) 0.0001(8) 0.0023(8) 0.0011(9)
C4 0.0226(10) 0.0230(11) 0.0246(10) -0.0026(9) 0.0007(8) 0.0020(9)
C5 0.0240(11) 0.0217(11) 0.0267(11) 0.0041(9) 0.0036(9) 0.0022(9)
C6 0.0238(11) 0.0254(12) 0.0225(10) 0.0030(9) 0.0019(8) 0.0055(9)
N7 0.0302(10) 0.0243(10) 0.0216(9) 0.0000(8) 0.0022(7) 0.0014(8)
O8 0.0446(11) 0.0428(11) 0.0304(9) -0.0009(8) 0.0121(8) -0.0148(9)
O9 0.0438(10) 0.0378(10) 0.0233(8) -0.0019(7) -0.0049(7) -0.0041(8)
N10 0.0343(10) 0.0223(10) 0.0330(10) 0.0028(8) 0.0109(8) 0.0024(8)
O11 0.0479(10) 0.0275(10) 0.0441(10) -0.0035(8) 0.0108(8) -0.0102(8)
O12 0.0654(13) 0.0345(11) 0.0328(10) 0.0111(8) 0.0114(9) -0.0015(9)
C13 0.0284(11) 0.0292(13) 0.0253(10) -0.0050(9) 0.0000(9) -0.0022(10)
C14 0.0374(13) 0.0221(11) 0.0317(12) -0.0040(9) 0.0010(10) -0.0001(10)
C15 0.0342(13) 0.0306(13) 0.0287(11) -0.0049(10) 0.0013(10) 0.0066(10)
C16 0.0237(11) 0.0312(13) 0.0279(11) -0.0011(10) 0.0019(8) 0.0078(10)
C17 0.0354(13) 0.0373(15) 0.0304(12) 0.0026(10) 0.0062(10) 0.0051(11)
C18 0.0350(13) 0.0359(14) 0.0432(14) 0.0093(12) 0.0078(11) -0.0007(11)
C19 0.0272(12) 0.0317(14) 0.0465(14) -0.0023(11) -0.0043(11) 0.0006(10)
C20 0.0273(11) 0.0369(13) 0.0315(12) 0.0013(10) -0.0046(10) 0.0039(11)
C21 0.0257(11) 0.0302(12) 0.0281(11) 0.0061(10) -0.0014(8) 0.0050(10)
C22 0.0330(12) 0.0378(14) 0.0285(12) -0.0102(11) -0.0024(9) 0.0058(11)
C23 0.0600(18) 0.052(2) 0.0267(13) -0.0061(12) -0.0037(11) 0.0181(15)

_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
N1 C6 1.340(3) . ?
N1 C2 1.422(3) . ?
N1 C13 1.505(3) . ?
C2 O2 1.214(3) . ?
C2 C3 1.450(3) . ?
C3 C4 1.355(3) . ?
C3 N7 1.465(3) . ?
C4 C5 1.404(3) . ?
C5 C6 1.356(3) . ?
C5 N10 1.451(3) . ?
N7 O9 1.221(3) . ?
N7 O8 1.223(3) . ?
N10 O11 1.221(3) . ?
N10 O12 1.225(3) . ?
C13 C22 1.466(3) . ?
C13 C14 1.543(3) . ?
C14 C15 1.533(3) . ?
C15 C16 1.514(4) . ?
C16 C17 1.392(4) . ?
C16 C21 1.399(3) . ?
C17 C18 1.386(4) . ?
C18 C19 1.384(4) . ?
C19 C20 1.388(4) . ?
C20 C21 1.383(4) . ?
C22 C23 1.173(4) . ?

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
C6 N1 C2 123.35(19) . . ?
C6 N1 C13 121.54(18) . . ?
C2 N1 C13 115.01(18) . . ?
O2 C2 N1 120.2(2) . . ?
O2 C2 C3 127.1(2) . . ?
N1 C2 C3 112.67(19) . . ?
C4 C3 C2 124.37(19) . . ?
C4 C3 N7 117.48(19) . . ?
C2 C3 N7 118.14(19) . . ?
C3 C4 C5 117.4(2) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 N10 119.05(19) . . ?
C4 C5 N10 119.9(2) . . ?
N1 C6 C5 120.98(19) . . ?
O9 N7 O8 123.95(19) . . ?
O9 N7 C3 117.70(18) . . ?
O8 N7 C3 118.33(19) . . ?
O11 N10 O12 124.3(2) . . ?
O11 N10 C5 117.86(18) . . ?
O12 N10 C5 117.9(2) . . ?
C22 C13 N1 109.9(2) . . ?
C22 C13 C14 112.4(2) . . ?
N1 C13 C14 111.42(18) . . ?
C15 C14 C13 116.6(2) . . ?
C16 C15 C14 116.42(19) . . ?
C17 C16 C21 117.9(2) . . ?
C17 C16 C15 120.3(2) . . ?
C21 C16 C15 121.8(2) . . ?
C18 C17 C16 121.3(2) . . ?
C19 C18 C17 120.2(2) . . ?
C18 C19 C20 119.3(2) . . ?
C21 C20 C19 120.5(2) . . ?
C20 C21 C16 120.8(2) . . ?
C23 C22 C13 177.3(3) . . ?

_refine_diff_density_max    0.153
_refine_diff_density_min   -0.148
_refine_diff_density_rms    0.035



#===END
