 
data_mo_ZZX752_2_a
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_formula_moiety          'C15 H14 N2 O2'
_chemical_formula_sum             'C15 H14 N2 O2' 
_chemical_formula_weight          254.28

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 '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'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 '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/n'
_space_group_name_Hall            '-P 2yn'
 
_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+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    7.5188(6)
_cell_length_b                    12.0570(10)
_cell_length_c                    14.2757(12)
_cell_angle_alpha                 90
_cell_angle_beta                  95.497(3)
_cell_angle_gamma                 90
_cell_volume                      1288.20(18)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     6134
_cell_measurement_theta_min       2.215
_cell_measurement_theta_max       28.266
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_diffrn     1.311          
_exptl_crystal_F_000              536
_exptl_crystal_size_max           0.590
_exptl_crystal_size_mid           0.330
_exptl_crystal_size_min           0.230
_exptl_absorpt_coefficient_mu     0.089
_shelx_estimated_absorpt_T_min    0.950
_shelx_estimated_absorpt_T_max    0.980
_exptl_absorpt_correction_type    numerical
_exptl_absorpt_correction_T_min   0.5363
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details 
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
; 
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed X-ray tube' 
_diffrn_measurement_device        'κ-geometry diffractometer'
_diffrn_measurement_device_type   'Bruker D8 Venture dual source kappa CPAD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector                  CPAD
_diffrn_detector_area_resol_mean  7.41       
_diffrn_detector_dtime            0
_diffrn_detector_type             'Bruker Photon III C7'
_diffrn_reflns_number             13926
_diffrn_reflns_av_unetI/netI      0.0828
_diffrn_reflns_av_R_equivalents   0.0961
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          2.215
_diffrn_reflns_theta_max          28.343
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.987
_diffrn_measured_fraction_theta_full  0.989
_diffrn_reflns_Laue_measured_fraction_max    0.987
_diffrn_reflns_Laue_measured_fraction_full   0.989
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              3165
_reflns_number_gt                 2224
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
 
_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        'Bruker APEX5 v2023-9.2 (Bruker AXS, 2023)' 
_computing_cell_refinement        'Bruker APEX5 v2023-9.2 (Bruker AXS, 2023)' 
_computing_data_reduction         'Bruker SAINT v8.40B (Bruker AXS, 2023)' 
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement   'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'OLEX2 v1.5 (Dolomanov et al, 2009)' 
_computing_publication_material   'CIFTAB v2014/2 (Sheldrick, 2014)' 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1986P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    diffmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_number_reflns          3165
_refine_ls_number_parameters      174
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1174
_refine_ls_R_factor_gt            0.0887
_refine_ls_wR_factor_ref          0.2908
_refine_ls_wR_factor_gt           0.2660
_refine_ls_goodness_of_fit_ref    1.076
_refine_ls_restrained_S_all       1.076
_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
C1 C 0.6583(3) 0.44393(19) 0.11669(18) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.5000(3) 0.3883(2) 0.15632(18) 0.0186(6) Uani 1 1 d . . . . .
C3 C 0.5932(3) 0.3460(2) 0.25217(18) 0.0188(6) Uani 1 1 d . . . . .
H3A H 0.513301 0.307823 0.292997 0.023 Uiso 1 1 calc R U . . .
H3B H 0.705657 0.304541 0.247571 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6171(3) 0.4719(2) 0.27094(18) 0.0162(6) Uani 1 1 d . . . . .
C5 C 0.4344(3) 0.4888(2) 0.21310(19) 0.0203(6) Uani 1 1 d . . . . .
H5A H 0.421966 0.559442 0.177735 0.024 Uiso 1 1 calc R U . . .
H5B H 0.329051 0.473457 0.247682 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3819(4) 0.3175(2) 0.09008(19) 0.0252(6) Uani 1 1 d . . . . .
H6A H 0.278509 0.292757 0.121415 0.038 Uiso 1 1 calc R U . . .
H6B H 0.449226 0.252808 0.071565 0.038 Uiso 1 1 calc R U . . .
H6C H 0.340873 0.360741 0.034002 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6620(3) 0.5205(2) 0.36625(17) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.7375(3) 0.4549(2) 0.43961(19) 0.0188(6) Uani 1 1 d . . . . .
H8 H 0.752986 0.377652 0.429835 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7905(4) 0.5008(2) 0.52703(18) 0.0195(6) Uani 1 1 d . . . . .
H9 H 0.842599 0.455665 0.576884 0.023 Uiso 1 1 calc R U . . .
C10 C 0.7662(3) 0.6140(2) 0.54056(18) 0.0193(6) Uani 1 1 d . . . . .
C11 C 0.6788(3) 0.6793(2) 0.46929(18) 0.0211(6) Uani 1 1 d . . . . .
H11 H 0.656136 0.755446 0.480274 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6259(3) 0.6323(2) 0.38301(19) 0.0201(6) Uani 1 1 d . . . . .
H12 H 0.564765 0.676026 0.334763 0.024 Uiso 1 1 calc R U . . .
C13 C 0.8375(3) 0.6647(2) 0.62718(19) 0.0220(6) Uani 1 1 d . . . . .
C14 C 0.9056(3) 0.55135(19) 0.20830(19) 0.0165(6) Uani 1 1 d . . . . .
C15 C 0.9983(3) 0.5712(2) 0.12123(19) 0.0241(6) Uani 1 1 d . . . . .
H15A H 0.916335 0.608631 0.073908 0.036 Uiso 1 1 calc R U . . .
H15B H 1.035196 0.499988 0.096161 0.036 Uiso 1 1 calc R U . . .
H15C H 1.103751 0.617762 0.136780 0.036 Uiso 1 1 calc R U . . .
N1 N 0.7389(3) 0.50092(17) 0.19629(15) 0.0173(5) Uani 1 1 d . . . . .
N2 N 0.8976(3) 0.7056(2) 0.69597(17) 0.0309(6) Uani 1 1 d . . . . .
O1 O 0.7060(2) 0.44030(14) 0.03845(12) 0.0226(5) Uani 1 1 d . . . . .
O2 O 0.9716(2) 0.57968(15) 0.28565(13) 0.0220(5) Uani 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
C1 O1 1.206(3) . ?
C1 N1 1.414(3) . ?
C1 C2 1.521(3) . ?
C2 C6 1.500(4) . ?
C2 C3 1.562(4) . ?
C2 C5 1.563(3) . ?
C3 C4 1.548(3) . ?
C4 C7 1.490(3) . ?
C4 N1 1.511(3) . ?
C4 C5 1.547(4) . ?
C7 C8 1.389(4) . ?
C7 C12 1.401(3) . ?
C8 C9 1.388(4) . ?
C9 C10 1.393(4) . ?
C10 C11 1.399(4) . ?
C10 C13 1.437(4) . ?
C11 C12 1.379(4) . ?
C13 N2 1.152(4) . ?
C14 O2 1.215(3) . ?
C14 N1 1.389(3) . ?
C14 C15 1.501(3) . ?
 
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
O1 C1 N1 128.2(2) . . ?
O1 C1 C2 129.9(2) . . ?
N1 C1 C2 101.87(19) . . ?
C6 C2 C1 116.9(2) . . ?
C6 C2 C3 123.7(2) . . ?
C1 C2 C3 99.7(2) . . ?
C6 C2 C5 124.8(2) . . ?
C1 C2 C5 98.54(19) . . ?
C3 C2 C5 86.34(19) . . ?
C4 C3 C2 82.33(18) . . ?
C7 C4 N1 116.94(19) . . ?
C7 C4 C5 123.21(19) . . ?
N1 C4 C5 99.23(19) . . ?
C7 C4 C3 123.8(2) . . ?
N1 C4 C3 99.97(17) . . ?
C5 C4 C3 87.39(19) . . ?
C4 C5 C2 82.32(18) . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 C4 120.3(2) . . ?
C12 C7 C4 120.2(2) . . ?
C9 C8 C7 120.8(2) . . ?
C8 C9 C10 119.0(2) . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 C13 119.5(3) . . ?
C11 C10 C13 119.8(2) . . ?
C12 C11 C10 119.6(2) . . ?
C11 C12 C7 120.2(3) . . ?
N2 C13 C10 178.8(2) . . ?
O2 C14 N1 121.3(2) . . ?
O2 C14 C15 121.8(2) . . ?
N1 C14 C15 116.9(2) . . ?
C14 N1 C1 128.6(2) . . ?
C14 N1 C4 128.0(2) . . ?
C1 N1 C4 102.23(18) . . ?
 
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 C6 -0.1(4) . . . . ?
N1 C1 C2 C6 -179.3(2) . . . . ?
O1 C1 C2 C3 135.9(3) . . . . ?
N1 C1 C2 C3 -43.3(2) . . . . ?
O1 C1 C2 C5 -136.4(3) . . . . ?
N1 C1 C2 C5 44.4(2) . . . . ?
C6 C2 C3 C4 -164.1(2) . . . . ?
C1 C2 C3 C4 64.09(18) . . . . ?
C5 C2 C3 C4 -33.96(16) . . . . ?
C2 C3 C4 C7 163.3(2) . . . . ?
C2 C3 C4 N1 -64.58(18) . . . . ?
C2 C3 C4 C5 34.33(16) . . . . ?
C7 C4 C5 C2 -163.7(2) . . . . ?
N1 C4 C5 C2 65.39(17) . . . . ?
C3 C4 C5 C2 -34.29(16) . . . . ?
C6 C2 C5 C4 163.2(2) . . . . ?
C1 C2 C5 C4 -65.3(2) . . . . ?
C3 C2 C5 C4 33.99(16) . . . . ?
N1 C4 C7 C8 -105.3(3) . . . . ?
C5 C4 C7 C8 131.5(2) . . . . ?
C3 C4 C7 C8 19.6(3) . . . . ?
N1 C4 C7 C12 75.7(3) . . . . ?
C5 C4 C7 C12 -47.5(3) . . . . ?
C3 C4 C7 C12 -159.3(2) . . . . ?
C12 C7 C8 C9 -5.2(3) . . . . ?
C4 C7 C8 C9 175.8(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 4.2(3) . . . . ?
C8 C9 C10 C13 -173.4(2) . . . . ?
C9 C10 C11 C12 -3.9(3) . . . . ?
C13 C10 C11 C12 173.7(2) . . . . ?
C10 C11 C12 C7 -1.1(3) . . . . ?
C8 C7 C12 C11 5.6(3) . . . . ?
C4 C7 C12 C11 -175.4(2) . . . . ?
O2 C14 N1 C1 -166.4(2) . . . . ?
C15 C14 N1 C1 14.8(3) . . . . ?
O2 C14 N1 C4 -0.9(4) . . . . ?
C15 C14 N1 C4 -179.7(2) . . . . ?
O1 C1 N1 C14 -11.3(4) . . . . ?
C2 C1 N1 C14 167.9(2) . . . . ?
O1 C1 N1 C4 -179.6(2) . . . . ?
C2 C1 N1 C4 -0.4(2) . . . . ?
C7 C4 N1 C14 12.4(3) . . . . ?
C5 C4 N1 C14 147.2(2) . . . . ?
C3 C4 N1 C14 -123.8(2) . . . . ?
C7 C4 N1 C1 -179.2(2) . . . . ?
C5 C4 N1 C1 -44.4(2) . . . . ?
C3 C4 N1 C1 44.6(2) . . . . ?
 
_refine_diff_density_max    0.530
_refine_diff_density_min   -0.528
_refine_diff_density_rms    0.126



