
data_CB2209

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C6 H8 N2 O2'
_chemical_formula_sum
 'C6 H8 N2 O2'
_chemical_formula_weight          140.14

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                    12.415(3)
_cell_length_b                    7.6131(15)
_cell_length_c                    6.9255(16)
_cell_angle_alpha                 90
_cell_angle_beta                  104.50(3)
_cell_angle_gamma                 90
_cell_volume                      633.7(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     343
_cell_measurement_theta_min       6.8990
_cell_measurement_theta_max       70.0210

_exptl_crystal_description        'thin needles'
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.469
_exptl_crystal_F_000              296
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.331
_exptl_crystal_size_mid           0.021
_exptl_crystal_size_min           0.011
_exptl_absorpt_coefficient_mu     0.946
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_correction_T_min   0.901
_exptl_absorpt_correction_T_max   0.990
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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  10.4115
_diffrn_reflns_number             2038
_diffrn_reflns_av_unetI/netI      0.0949
_diffrn_reflns_av_R_equivalents   0.0807
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          3.678
_diffrn_reflns_theta_max          73.653
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.949
_diffrn_measured_fraction_theta_full  0.979
_diffrn_reflns_Laue_measured_fraction_max    0.949
_diffrn_reflns_Laue_measured_fraction_full   0.979
_diffrn_reflns_point_group_measured_fraction_max   0.949
_diffrn_reflns_point_group_measured_fraction_full  0.979
_reflns_number_total              2038
_reflns_number_gt                 958
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

_reflns_special_details
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection        'CrysAlisPro, Rigaku OD'
_computing_cell_refinement        'CrysAlisPro, Rigaku OD'
_computing_data_reduction         'CrysAlisPro, Rigaku OD'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1329P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2038
_refine_ls_number_parameters      102
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.1401
_refine_ls_R_factor_gt            0.0781
_refine_ls_wR_factor_ref          0.2277
_refine_ls_wR_factor_gt           0.1915
_refine_ls_goodness_of_fit_ref    0.873
_refine_ls_restrained_S_all       0.873
_refine_ls_shift/su_max           0.001
_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 0.3752(4) 0.6539(4) 0.6025(6) 0.0272(11) Uani 1 1 d D . . . .
H1 H 0.3996(12) 0.5439(6) 0.635(3) 0.046(18) Uiso 1 1 d D . . . .
C2 C 0.4391(4) 0.7962(7) 0.6690(6) 0.0280(11) Uani 1 1 d . . . . .
O2 O 0.5352(3) 0.7964(5) 0.7780(5) 0.0316(9) Uani 1 1 d . . . . .
N3 N 0.3776(4) 0.9436(4) 0.5955(6) 0.0299(11) Uani 1 1 d D . . . .
H3 H 0.4012(12) 1.0552(6) 0.619(5) 0.05(2) Uiso 1 1 d D . . . .
C4 C 0.2712(5) 0.8978(8) 0.4835(7) 0.0300(13) Uani 1 1 d . . . . .
O4 O 0.2001(3) 1.0031(5) 0.4047(6) 0.0349(10) Uani 1 1 d . . . . .
C5 C 0.2685(4) 0.7035(7) 0.4858(6) 0.0255(11) Uani 1 1 d . . . . .
C6 C 0.1859(4) 0.5955(7) 0.3987(7) 0.0261(12) Uani 1 1 d . . . . .
C7 C 0.0747(5) 0.6583(7) 0.2822(8) 0.0339(13) Uani 1 1 d . . . . .
H7A H 0.073669 0.787010 0.280808 0.051 Uiso 1 1 calc R U . . .
H7B H 0.017037 0.614810 0.344288 0.051 Uiso 1 1 calc R U . . .
H7C H 0.060298 0.614284 0.145169 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2003(5) 0.3991(8) 0.4152(8) 0.0356(13) Uani 1 1 d . . . . .
H8A H 0.274701 0.371504 0.498034 0.053 Uiso 1 1 calc R U . . .
H8B H 0.191581 0.348733 0.281941 0.053 Uiso 1 1 calc R U . . .
H8C H 0.144036 0.349207 0.476440 0.053 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 0.027(2) 0.019(3) 0.032(2) 0.0017(16) 0.0011(18) -0.0009(19)
C2 0.031(3) 0.027(3) 0.026(2) -0.001(2) 0.0056(19) -0.003(3)
O2 0.0269(19) 0.029(2) 0.0345(18) 0.0010(18) -0.0011(13) -0.0003(18)
N3 0.033(3) 0.022(2) 0.031(2) 0.0033(19) 0.0013(19) -0.002(2)
C4 0.029(3) 0.029(3) 0.031(3) 0.002(2) 0.004(2) -0.001(3)
O4 0.031(2) 0.0211(19) 0.047(2) 0.0020(17) -0.0019(17) 0.0038(18)
C5 0.033(3) 0.021(2) 0.021(2) 0.001(2) 0.0049(19) 0.002(3)
C6 0.031(3) 0.023(3) 0.023(2) 0.000(2) 0.003(2) 0.002(2)
C7 0.028(3) 0.029(3) 0.040(3) 0.000(2) 0.001(2) -0.004(2)
C8 0.033(3) 0.028(3) 0.040(3) -0.001(2) 0.000(2) -0.004(3)

_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 C2 1.354(6) . ?
N1 C5 1.419(7) . ?
C2 O2 1.242(6) . ?
C2 N3 1.381(7) . ?
N3 C4 1.398(7) . ?
C4 O4 1.216(7) . ?
C4 C5 1.480(7) . ?
C5 C6 1.334(7) . ?
C6 C7 1.493(7) . ?
C6 C8 1.507(7) . ?

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 N1 C5 111.4(4) . . ?
O2 C2 N1 126.8(5) . . ?
O2 C2 N3 125.6(5) . . ?
N1 C2 N3 107.6(4) . . ?
C2 N3 C4 111.1(4) . . ?
O4 C4 N3 124.3(5) . . ?
O4 C4 C5 130.4(6) . . ?
N3 C4 C5 105.3(5) . . ?
C6 C5 N1 126.6(5) . . ?
C6 C5 C4 128.9(5) . . ?
N1 C5 C4 104.6(5) . . ?
C5 C6 C7 123.3(5) . . ?
C5 C6 C8 120.9(5) . . ?
C7 C6 C8 115.8(5) . . ?

loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
 _geom_hbond_publ_flag
N1 H1 O2  0.9000(2) 2.080(5) 2.978(5) 176.4(13) 2_646 yes
N3 H3 O2  0.9000(3) 2.054(8) 2.945(5) 170(3) 2_656 yes

_refine_diff_density_max    0.616
_refine_diff_density_min   -0.369
_refine_diff_density_rms    0.101



#===END
