data_global
_audit_creation_method                  'APEX3 v2017.3-0'

_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_cyg295s
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C24 H16 N2 O3'
_chemical_formula_iupac                 ?
_chemical_formula_weight                380.39
_chemical_absolute_configuration        ad

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21 1'
_space_group_name_Hall                  'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'

_cell_length_a                          9.2224(2)
_cell_length_b                          8.9700(2)
_cell_length_c                          11.9200(3)
_cell_angle_alpha                       90
_cell_angle_beta                        112.4768(9)
_cell_angle_gamma                       90
_cell_volume                            911.17(4)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           8604
_cell_measurement_theta_min             4.0135
_cell_measurement_theta_max             66.2922
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              plate
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.280
_exptl_crystal_size_mid                 0.200
_exptl_crystal_size_min                 0.020
_exptl_crystal_density_diffrn           1.386
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    396

_exptl_absorpt_coefficient_mu           0.752
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.56
_exptl_absorpt_correction_T_max         0.98

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'Incoatec Microfocus Source'
_diffrn_source_type                     'Bruker Kappa Duo APEX2'

_diffrn_radiation_type                  CuK\a
_diffrn_radiation_wavelength            1.54178
_diffrn_radiation_monochromator         'Multilayer Mirror'

_diffrn_measurement_device_type         'CCD area detector'
_diffrn_measurement_method              'phi and omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   11583
_diffrn_reflns_av_R_equivalents         0.0653
_diffrn_reflns_av_unetI/netI            0.0591
_diffrn_reflns_theta_min                4.01
_diffrn_reflns_theta_max                66.59
_diffrn_reflns_theta_full               66.59
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full    0.999
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -10
_diffrn_reflns_limit_k_max              9
_diffrn_reflns_limit_l_min              -14
_diffrn_reflns_limit_l_max              14

_refine_special_details                 
;
;

_reflns_number_total                    3123
_reflns_number_gt                       3021
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0482
_refine_ls_R_factor_gt                  0.0473
_refine_ls_wR_factor_gt                 0.1163
_refine_ls_wR_factor_ref                0.1170
_refine_ls_goodness_of_fit_ref          1.083
_refine_ls_restrained_S_all             1.083
_refine_ls_number_reflns                3123
_refine_ls_number_parameters            262
_refine_ls_number_restraints            1
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0836P)²] 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                0.320
_refine_diff_density_min                -0.395
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?
_refine_ls_abs_structure_details        
;

Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          0.06(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'

_computing_data_collection              'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement              'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction               'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution           'XT, VERSION 2014/5'
_computing_structure_refinement         'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics           'XP (Bruker AXS Inc., 2017)'
_computing_publication_material         'APEX3 (Bruker AXS Inc., 2017)'

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 0.1458(3) 0.3425(3) 0.5469(3) 0.0205(6) Uani d . . . 1 . .
    C C2 0.1584(3) 0.2633(3) 0.6575(2) 0.0207(6) Uani d . . . 1 . .
    C C3 0.0653(3) 0.1444(3) 0.6638(3) 0.0236(6) Uani d . . . 1 . .
    H H3 -0.011857 0.104249 0.59205 0.028 Uiso calc U . R 1 . .
    C C4 0.0870(4) 0.0846(3) 0.7780(3) 0.0271(6) Uani d . . . 1 . .
    H H4 0.022035 0.004326 0.7823 0.033 Uiso calc U . R 1 . .
    C C5 0.1998(3) 0.1385(3) 0.8849(3) 0.0265(6) Uani d . . . 1 . .
    H H5 0.210386 0.096146 0.960638 0.032 Uiso calc U . R 1 . .
    C C6 0.2982(3) 0.2555(3) 0.8806(3) 0.0227(6) Uani d . . . 1 . .
    C C7 0.2698(3) 0.3155(3) 0.7647(2) 0.0200(6) Uani d . . . 1 . .
    C C8 0.4652(3) 0.4472(3) 0.8965(3) 0.0242(6) Uani d . . . 1 . .
    H H8 0.547318 0.518166 0.928287 0.029 Uiso calc U . R 1 . .
    C C9 0.4258(3) 0.3427(3) 0.9630(3) 0.0264(6) Uani d . . . 1 . .
    H H9 0.474003 0.329622 1.048424 0.032 Uiso calc U . R 1 . .
    C C10 0.3860(3) 0.4883(3) 0.6667(3) 0.0198(6) Uani d . . . 1 . .
    C C11 0.5247(3) 0.4027(3) 0.6506(2) 0.0207(6) Uani d . . . 1 . .
    C C12 0.5825(3) 0.6532(3) 0.6649(2) 0.0196(6) Uani d . . . 1 . .
    C C13 0.4350(3) 0.6482(3) 0.6731(3) 0.0198(6) Uani d . . . 1 . .
    C C14 0.3573(3) 0.7774(3) 0.6793(2) 0.0222(6) Uani d . . . 1 . .
    H H14 0.256592 0.773805 0.683655 0.027 Uiso calc U . R 1 . .
    C C15 0.4304(3) 0.9137(3) 0.6791(3) 0.0225(6) Uani d . . . 1 . .
    H H15 0.379418 1.004148 0.683566 0.027 Uiso calc U . R 1 . .
    C C16 0.5783(3) 0.9176(3) 0.6722(3) 0.0230(6) Uani d . . . 1 . .
    H H16 0.62628 1.011214 0.671784 0.028 Uiso calc U . R 1 . .
    C C17 0.6569(3) 0.7868(3) 0.6660(2) 0.0220(6) Uani d . . . 1 . .
    H H17 0.758175 0.789789 0.662657 0.026 Uiso calc U . R 1 . .
    C C18 0.7885(3) 0.4711(3) 0.6529(3) 0.0227(6) Uani d . . . 1 . .
    H H18A 0.809718 0.535093 0.593224 0.027 Uiso calc U . R 1 . .
    H H18B 0.789327 0.365961 0.627858 0.027 Uiso calc U . R 1 . .
    C C19 0.9158(3) 0.4940(3) 0.7771(3) 0.0220(6) Uani d . . . 1 . .
    C C20 0.9189(3) 0.4069(3) 0.8748(3) 0.0251(6) Uani d . . . 1 . .
    H H20 0.840851 0.332773 0.863126 0.03 Uiso calc U . R 1 . .
    C C21 1.0353(4) 0.4280(3) 0.9892(3) 0.0300(7) Uani d . . . 1 . .
    H H21 1.037214 0.367421 1.055096 0.036 Uiso calc U . R 1 . .
    C C22 1.1488(4) 0.5368(3) 1.0077(3) 0.0308(7) Uani d . . . 1 . .
    H H22 1.227361 0.55211 1.086304 0.037 Uiso calc U . R 1 . .
    C C23 1.1470(4) 0.6236(3) 0.9104(3) 0.0298(7) Uani d . . . 1 . .
    H H23 1.225008 0.697753 0.922366 0.036 Uiso calc U . R 1 . .
    C C24 1.0314(3) 0.6018(3) 0.7960(3) 0.0241(6) Uani d . . . 1 . .
    H H24 1.031054 0.661058 0.729826 0.029 Uiso calc U . R 1 . .
    N N1 0.3667(3) 0.4340(2) 0.7752(2) 0.0198(5) Uani d . . . 1 . .
    N N2 0.6334(3) 0.5076(2) 0.6532(2) 0.0207(5) Uani d . . . 1 . .
    O O1 0.0529(2) 0.3180(2) 0.44579(17) 0.0248(4) Uani d . . . 1 . .
    O O2 0.2444(2) 0.4636(2) 0.56193(17) 0.0212(4) Uani d . . . 1 . .
    O O3 0.5318(2) 0.2694(2) 0.64170(19) 0.0274(5) 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 O1 . 1.203(3) ?
    C1 O2 . 1.384(3) ?
    C1 C2 . 1.461(4) ?
    C2 C7 . 1.380(4) ?
    C2 C3 . 1.389(4) ?
    C3 C4 . 1.405(4) ?
    C3 H3 . 0.95 ?
    C4 C5 . 1.387(5) ?
    C4 H4 . 0.95 ?
    C5 C6 . 1.400(4) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.411(4) ?
    C6 C9 . 1.441(4) ?
    C7 N1 . 1.364(3) ?
    C8 C9 . 1.364(4) ?
    C8 N1 . 1.387(4) ?
    C8 H8 . 0.95 ?
    C9 H9 . 0.95 ?
    C10 O2 . 1.438(3) ?
    C10 N1 . 1.456(3) ?
    C10 C13 . 1.498(4) ?
    C10 C11 . 1.565(4) ?
    C11 O3 . 1.204(4) ?
    C11 N2 . 1.366(4) ?
    C12 C17 . 1.379(4) ?
    C12 C13 . 1.400(4) ?
    C12 N2 . 1.412(3) ?
    C13 C14 . 1.380(4) ?
    C14 C15 . 1.397(4) ?
    C14 H14 . 0.95 ?
    C15 C16 . 1.397(4) ?
    C15 H15 . 0.95 ?
    C16 C17 . 1.396(4) ?
    C16 H16 . 0.95 ?
    C17 H17 . 0.95 ?
    C18 N2 . 1.470(3) ?
    C18 C19 . 1.511(4) ?
    C18 H18A . 0.99 ?
    C18 H18B . 0.99 ?
    C19 C24 . 1.392(4) ?
    C19 C20 . 1.394(4) ?
    C20 C21 . 1.388(5) ?
    C20 H20 . 0.95 ?
    C21 C22 . 1.386(5) ?
    C21 H21 . 0.95 ?
    C22 C23 . 1.391(5) ?
    C22 H22 . 0.95 ?
    C23 C24 . 1.387(5) ?
    C23 H23 . 0.95 ?
    C24 H24 . 0.95 ?

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
    O1 C1 O2 . . 117.0(2) ?
    O1 C1 C2 . . 126.6(3) ?
    O2 C1 C2 . . 116.3(2) ?
    C7 C2 C3 . . 117.8(3) ?
    C7 C2 C1 . . 116.4(2) ?
    C3 C2 C1 . . 125.7(3) ?
    C2 C3 C4 . . 119.0(3) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 120.5 ?
    C5 C4 C3 . . 122.3(3) ?
    C5 C4 H4 . . 118.8 ?
    C3 C4 H4 . . 118.8 ?
    C4 C5 C6 . . 119.8(3) ?
    C4 C5 H5 . . 120.1 ?
    C6 C5 H5 . . 120.1 ?
    C5 C6 C7 . . 116.2(3) ?
    C5 C6 C9 . . 138.9(3) ?
    C7 C6 C9 . . 104.9(2) ?
    N1 C7 C2 . . 125.4(2) ?
    N1 C7 C6 . . 109.8(2) ?
    C2 C7 C6 . . 124.9(3) ?
    C9 C8 N1 . . 109.5(2) ?
    C9 C8 H8 . . 125.3 ?
    N1 C8 H8 . . 125.3 ?
    C8 C9 C6 . . 107.9(3) ?
    C8 C9 H9 . . 126.1 ?
    C6 C9 H9 . . 126.1 ?
    O2 C10 N1 . . 110.0(2) ?
    O2 C10 C13 . . 110.4(2) ?
    N1 C10 C13 . . 114.3(2) ?
    O2 C10 C11 . . 109.4(2) ?
    N1 C10 C11 . . 109.1(2) ?
    C13 C10 C11 . . 103.4(2) ?
    O3 C11 N2 . . 128.4(3) ?
    O3 C11 C10 . . 124.9(3) ?
    N2 C11 C10 . . 106.6(2) ?
    C17 C12 C13 . . 121.3(2) ?
    C17 C12 N2 . . 128.4(2) ?
    C13 C12 N2 . . 110.2(2) ?
    C14 C13 C12 . . 121.1(2) ?
    C14 C13 C10 . . 130.9(3) ?
    C12 C13 C10 . . 108.0(2) ?
    C13 C14 C15 . . 118.2(2) ?
    C13 C14 H14 . . 120.9 ?
    C15 C14 H14 . . 120.9 ?
    C14 C15 C16 . . 120.4(2) ?
    C14 C15 H15 . . 119.8 ?
    C16 C15 H15 . . 119.8 ?
    C17 C16 C15 . . 121.3(2) ?
    C17 C16 H16 . . 119.3 ?
    C15 C16 H16 . . 119.3 ?
    C12 C17 C16 . . 117.7(2) ?
    C12 C17 H17 . . 121.2 ?
    C16 C17 H17 . . 121.2 ?
    N2 C18 C19 . . 111.1(2) ?
    N2 C18 H18A . . 109.4 ?
    C19 C18 H18A . . 109.4 ?
    N2 C18 H18B . . 109.4 ?
    C19 C18 H18B . . 109.4 ?
    H18A C18 H18B . . 108.0 ?
    C24 C19 C20 . . 119.0(3) ?
    C24 C19 C18 . . 120.8(3) ?
    C20 C19 C18 . . 120.2(3) ?
    C21 C20 C19 . . 120.3(3) ?
    C21 C20 H20 . . 119.8 ?
    C19 C20 H20 . . 119.8 ?
    C22 C21 C20 . . 120.4(3) ?
    C22 C21 H21 . . 119.8 ?
    C20 C21 H21 . . 119.8 ?
    C21 C22 C23 . . 119.6(3) ?
    C21 C22 H22 . . 120.2 ?
    C23 C22 H22 . . 120.2 ?
    C24 C23 C22 . . 120.1(3) ?
    C24 C23 H23 . . 120.0 ?
    C22 C23 H23 . . 120.0 ?
    C23 C24 C19 . . 120.6(3) ?
    C23 C24 H24 . . 119.7 ?
    C19 C24 H24 . . 119.7 ?
    C7 N1 C8 . . 107.9(2) ?
    C7 N1 C10 . . 118.5(2) ?
    C8 N1 C10 . . 130.1(2) ?
    C11 N2 C12 . . 111.8(2) ?
    C11 N2 C18 . . 123.6(2) ?
    C12 N2 C18 . . 124.5(2) ?
    C1 O2 C10 . . 124.5(2) ?



