data_global
_audit_creation_method                  'APEX5 v2023.9-2'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_scw3188c
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C18 H20 N2 O4'
_chemical_formula_iupac                 ?
_chemical_formula_weight                328.36

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_IT_number                  14
_space_group_name_H-M_alt               'P 1 21/c 1'
_space_group_name_Hall                  '-P 2ybc'
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                          14.2706(4)
_cell_length_b                          11.6188(3)
_cell_length_c                          10.3961(3)
_cell_angle_alpha                       90
_cell_angle_beta                        108.4964(11)
_cell_angle_gamma                       90
_cell_volume                            1634.71(8)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           9960
_cell_measurement_theta_min             5.8861
_cell_measurement_theta_max             68.3186
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.120
_exptl_crystal_size_mid                 0.100
_exptl_crystal_size_min                 0.080
_exptl_crystal_density_diffrn           1.334
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    696

_exptl_absorpt_coefficient_mu           0.781
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min         0.82
_exptl_absorpt_correction_T_max         0.94

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'Incoatec Microfocus Diamond 2'
_diffrn_source_type                     'Bruker D8 Quest'
_diffrn_source_power                    0.05
_diffrn_source_current                  1.0
_diffrn_source_voltage                  50

_diffrn_radiation_probe                 X-ray
_diffrn_radiation_type                  CuK\a
_diffrn_radiation_wavelength            1.54178
_diffrn_radiation_monochromator         'Multilayer Mirror'

_diffrn_measurement_device              'PHOTON 3'
_diffrn_measurement_device_type         'CCD area detector'
_diffrn_measurement_method              'phi and omega scans'

_diffrn_detector_area_resol_mean        7.3910

_diffrn_reflns_number                   13432
_diffrn_reflns_av_R_equivalents         0.0365
_diffrn_reflns_av_unetI/netI            0.0348
_diffrn_reflns_theta_min                3.27
_diffrn_reflns_theta_max                68.31
_diffrn_reflns_theta_full               67.68
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full    0.996
_diffrn_reflns_limit_h_min              -17
_diffrn_reflns_limit_h_max              16
_diffrn_reflns_limit_k_min              -14
_diffrn_reflns_limit_k_max              13
_diffrn_reflns_limit_l_min              -12
_diffrn_reflns_limit_l_max              12

_refine_special_details                 
;
;

_reflns_number_total                    2986
_reflns_number_gt                       2815
_reflns_threshold_expression            'I > 2σ(I)'
_reflns_Friedel_coverage                0.000
_reflns_Friedel_fraction_max            .
_reflns_Friedel_fraction_full           .

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0452
_refine_ls_R_factor_gt                  0.0436
_refine_ls_wR_factor_gt                 0.1181
_refine_ls_wR_factor_ref                0.1196
_refine_ls_goodness_of_fit_ref          1.075
_refine_ls_restrained_S_all             1.075
_refine_ls_number_reflns                2986
_refine_ls_number_parameters            219
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0655P)²+0.6475P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            dual
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.547
_refine_diff_density_min                -0.223
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

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'

_computing_data_collection              'APEX5 (Bruker AXS Inc., 2023)'
_computing_cell_refinement              'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction               'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution           'XT, VERSION 2018/2'
_computing_structure_refinement         'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics           'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material         'APEX5 (Bruker AXS Inc., 2023)'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.46378(10) 0.15018(11) 0.51496(15) 0.0199(3) Uani d . . . 1 . .
    C C2 0.52102(11) 0.15746(12) 0.65110(15) 0.0232(3) Uani d . . . 1 . .
    H H2 0.490334 0.162999 0.719695 0.028000 Uiso calc U . R 1 . .
    C C3 0.62332(11) 0.15652(12) 0.68543(15) 0.0241(3) Uani d . . . 1 . .
    H H3 0.660971 0.161870 0.778720 0.029000 Uiso calc U . R 1 . .
    C C4 0.61658(11) 0.14197(12) 0.46442(15) 0.0226(3) Uani d . . . 1 . .
    H H4 0.649268 0.136553 0.398022 0.027000 Uiso calc U . R 1 . .
    C C5 0.51380(10) 0.14262(11) 0.42021(15) 0.0216(3) Uani d . . . 1 . .
    H H5 0.478110 0.137942 0.326154 0.026000 Uiso calc U . R 1 . .
    C C6 0.35224(10) 0.14821(12) 0.47343(15) 0.0222(3) Uani d . . . 1 . .
    H H6A 0.331421 0.086127 0.523695 0.027000 Uiso calc U . R 1 . .
    H H6B 0.325426 0.130115 0.375491 0.027000 Uiso calc U . R 1 . .
    C C7 0.30818(9) 0.26260(11) 0.50049(13) 0.0182(3) Uani d . . . 1 . .
    H H7 0.332428 0.279840 0.599842 0.022000 Uiso calc U . R 1 . .
    C C8 0.33931(9) 0.35876(12) 0.42310(14) 0.0184(3) Uani d . . . 1 . .
    C C9 0.37683(12) 0.55525(13) 0.41916(17) 0.0321(4) Uani d . . . 1 . .
    H H9A 0.435478 0.538930 0.392495 0.048000 Uiso calc U . R 1 . .
    H H9B 0.388893 0.623540 0.477454 0.048000 Uiso calc U . R 1 . .
    H H9C 0.320184 0.569283 0.337901 0.048000 Uiso calc U . R 1 . .
    C C10 0.19310(9) 0.25875(11) 0.45012(13) 0.0187(3) Uani d . . . 1 . .
    H H10 0.171444 0.247659 0.349564 0.022000 Uiso calc U . R 1 . .
    C C11 0.15186(9) 0.37309(12) 0.47726(14) 0.0201(3) Uani d . . . 1 . .
    C C12 0.14114(11) 0.50564(14) 0.64387(16) 0.0301(4) Uani d . . . 1 . .
    H H12A 0.158543 0.565059 0.588502 0.045000 Uiso calc U . R 1 . .
    H H12B 0.174398 0.521851 0.740107 0.045000 Uiso calc U . R 1 . .
    H H12C 0.069445 0.505450 0.625892 0.045000 Uiso calc U . R 1 . .
    C C13 0.15107(10) 0.15779(12) 0.51074(15) 0.0213(3) Uani d . . . 1 . .
    H H13A 0.175159 0.084421 0.484322 0.026000 Uiso calc U . R 1 . .
    H H13B 0.175789 0.163126 0.610934 0.026000 Uiso calc U . R 1 . .
    C C14 0.03911(10) 0.15690(11) 0.46362(14) 0.0194(3) Uani d . . . 1 . .
    C C15 -0.01633(11) 0.16109(13) 0.32692(15) 0.0252(3) Uani d . . . 1 . .
    H H15 0.015719 0.164511 0.259667 0.030000 Uiso calc U . R 1 . .
    C C16 -0.11862(11) 0.16025(14) 0.28936(15) 0.0270(3) Uani d . . . 1 . .
    H H16 -0.154765 0.163175 0.195352 0.032000 Uiso calc U . R 1 . .
    C C17 -0.11568(11) 0.14988(12) 0.50824(15) 0.0247(3) Uani d . . . 1 . .
    H H17 -0.149789 0.145437 0.573100 0.030000 Uiso calc U . R 1 . .
    C C18 -0.01311(11) 0.15004(12) 0.55569(15) 0.0229(3) Uani d . . . 1 . .
    H H18 0.021055 0.145504 0.650235 0.027000 Uiso calc U . R 1 . .
    N N1 0.67219(9) 0.14852(10) 0.59479(13) 0.0231(3) Uani d . . . 1 . .
    N N2 -0.16952(9) 0.15558(11) 0.37722(13) 0.0253(3) Uani d . . . 1 . .
    O O1 0.35594(7) 0.45716(8) 0.49288(10) 0.0239(3) Uani d . . . 1 . .
    O O2 0.17241(7) 0.39348(9) 0.60985(10) 0.0244(3) Uani d . . . 1 . .
    O O3 0.34590(7) 0.34889(9) 0.31093(10) 0.0265(3) Uani d . . . 1 . .
    O O4 0.10630(8) 0.43849(9) 0.38980(10) 0.0289(3) Uani d . . . 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C5 . 1.391(2) ?
    C1 C2 . 1.394(2) ?
    C1 C6 . 1.5114(19) ?
    C2 C3 . 1.389(2) ?
    C3 N1 . 1.3416(19) ?
    C4 N1 . 1.338(2) ?
    C4 C5 . 1.391(2) ?
    C6 C7 . 1.5340(18) ?
    C7 C8 . 1.5231(18) ?
    C7 C10 . 1.5581(18) ?
    C8 O3 . 1.2048(18) ?
    C8 O1 . 1.3344(17) ?
    C9 O1 . 1.4560(17) ?
    C10 C11 . 1.5152(18) ?
    C10 C13 . 1.5404(18) ?
    C11 O4 . 1.2049(17) ?
    C11 O2 . 1.3363(17) ?
    C12 O2 . 1.4569(17) ?
    C13 C14 . 1.5153(18) ?
    C14 C18 . 1.389(2) ?
    C14 C15 . 1.391(2) ?
    C15 C16 . 1.386(2) ?
    C16 N2 . 1.336(2) ?
    C17 N2 . 1.336(2) ?
    C17 C18 . 1.388(2) ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 C1 C2 . . 117.11(13) ?
    C5 C1 C6 . . 121.83(13) ?
    C2 C1 C6 . . 121.04(13) ?
    C3 C2 C1 . . 119.34(13) ?
    N1 C3 C2 . . 123.95(14) ?
    N1 C4 C5 . . 123.98(13) ?
    C1 C5 C4 . . 119.39(13) ?
    C1 C6 C7 . . 112.97(11) ?
    C8 C7 C6 . . 109.48(11) ?
    C8 C7 C10 . . 107.25(10) ?
    C6 C7 C10 . . 111.30(10) ?
    O3 C8 O1 . . 123.56(13) ?
    O3 C8 C7 . . 124.53(12) ?
    O1 C8 C7 . . 111.89(11) ?
    C11 C10 C13 . . 111.52(11) ?
    C11 C10 C7 . . 110.03(10) ?
    C13 C10 C7 . . 112.95(11) ?
    O4 C11 O2 . . 123.77(13) ?
    O4 C11 C10 . . 124.11(13) ?
    O2 C11 C10 . . 112.11(11) ?
    C14 C13 C10 . . 112.35(11) ?
    C18 C14 C15 . . 116.76(13) ?
    C18 C14 C13 . . 121.24(12) ?
    C15 C14 C13 . . 121.99(12) ?
    C16 C15 C14 . . 119.63(13) ?
    N2 C16 C15 . . 124.05(13) ?
    N2 C17 C18 . . 124.23(13) ?
    C17 C18 C14 . . 119.39(13) ?
    C4 N1 C3 . . 116.23(12) ?
    C16 N2 C17 . . 115.92(12) ?
    C8 O1 C9 . . 114.54(11) ?
    C11 O2 C12 . . 115.16(11) ?



