 
data_23050z
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             23050z
_chemical_melting_point           ?
_chemical_formula_moiety          'C26 H14 N2 O4'
_chemical_formula_sum             'C26 H14 N2 O4' 
_chemical_formula_weight          418.39

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       orthorhombic
_space_group_IT_number            60
_space_group_name_H-M_alt         'P b c n'
_space_group_name_Hall            '-P 2n 2ab'
 
_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+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 'x, -y, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    26.4699(18)
_cell_length_b                    10.3060(7)
_cell_length_c                    7.0470(4)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1922.4(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     130(2)
_cell_measurement_reflns_used     2919
_cell_measurement_theta_min       3.04
_cell_measurement_theta_max       30.43

_exptl_crystal_description       'block'
_exptl_crystal_colour            'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.446          
_exptl_crystal_F_000              864
_exptl_transmission_factor_min    0.6331
_exptl_transmission_factor_max    0.7461
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.140
_exptl_absorpt_coefficient_mu     0.099
_shelx_estimated_absorpt_T_min    0.6331
_shelx_estimated_absorpt_T_max    0.7461
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.4990
_exptl_absorpt_correction_T_max   0.7457
_exptl_absorpt_process_details    'SADABS-2016/2, (Sheldrick, 2016)'
_exptl_absorpt_special_details    ?
_exptl_special_details            'Prof. D. Cao - Macalester College'
_diffrn_ambient_temperature       130(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'micro-focus'
_diffrn_measurement_device_type   'Bruker PHOTON-III CPAD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             17748
_diffrn_reflns_av_unetI/netI      0.0234
_diffrn_reflns_av_R_equivalents   0.0342
_diffrn_reflns_limit_h_min        -37
_diffrn_reflns_limit_h_max        30
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          2.121
_diffrn_reflns_theta_max          30.556
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              2942
_reflns_number_gt                 2570
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0610P)²+0.5894P] 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      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2942
_refine_ls_number_parameters      145
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0458
_refine_ls_R_factor_gt            0.0404
_refine_ls_wR_factor_ref          0.1127
_refine_ls_wR_factor_gt           0.1071
_refine_ls_goodness_of_fit_ref    1.058
_refine_ls_restrained_S_all       1.058
_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
O1 O 0.36739(3) 0.49879(7) 0.55687(11) 0.02323(18) Uani 1 1 d . . . . .
O2 O 0.44222(3) 0.88254(7) 0.72968(12) 0.02318(18) Uani 1 1 d . . . . .
N1 N 0.39307(3) 0.70877(8) 0.62971(12) 0.01624(17) Uani 1 1 d . . . . .
C1 C 0.39856(4) 0.57365(9) 0.61816(13) 0.01619(18) Uani 1 1 d . . . . .
C6 C 0.44951(4) 0.30283(9) 0.68557(15) 0.0198(2) Uani 1 1 d . . . . .
H6 H 0.415491 0.301432 0.642640 0.024 Uiso 1 1 calc R U . . .
C7 C 0.47476(4) 0.18855(10) 0.71768(16) 0.0237(2) Uani 1 1 d . . . . .
H7 H 0.458021 0.108346 0.696103 0.028 Uiso 1 1 calc R U . . .
C8 C 0.34759(3) 0.77857(9) 0.58862(13) 0.01654(19) Uani 1 1 d . . . . .
C9 C 0.30173(4) 0.73150(10) 0.65547(14) 0.0195(2) Uani 1 1 d . . . . .
H9 H 0.300364 0.651981 0.723474 0.023 Uiso 1 1 calc R U . . .
C10 C 0.25785(4) 0.80205(11) 0.62176(16) 0.0238(2) Uani 1 1 d . . . . .
H10 H 0.226235 0.769953 0.664983 0.029 Uiso 1 1 calc R U . . .
C11 C 0.26014(4) 0.91918(11) 0.52514(16) 0.0247(2) Uani 1 1 d . . . . .
H11 H 0.230195 0.967921 0.504237 0.030 Uiso 1 1 calc R U . . .
C12 C 0.30618(4) 0.96521(11) 0.45897(15) 0.0236(2) Uani 1 1 d . . . . .
H12 H 0.307582 1.045502 0.392957 0.028 Uiso 1 1 calc R U . . .
C13 C 0.35027(4) 0.89466(10) 0.48862(15) 0.0206(2) Uani 1 1 d . . . . .
H13 H 0.381695 0.925275 0.441336 0.025 Uiso 1 1 calc R U . . .
C2 C 0.45084(3) 0.54486(9) 0.68792(13) 0.01455(18) Uani 1 1 d . . . . .
C3 C 0.47472(3) 0.66163(9) 0.72113(13) 0.01403(18) Uani 1 1 d . . . . .
C4 C 0.43755(3) 0.76877(9) 0.69514(13) 0.01579(18) Uani 1 1 d . . . . .
C5 C 0.47431(3) 0.42301(9) 0.71663(13) 0.01515(19) 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
O1 C1 1.2094(12) . ?
O2 C4 1.2038(12) . ?
N1 C1 1.4024(12) . ?
N1 C4 1.4075(12) . ?
N1 C8 1.4321(12) . ?
C1 C2 1.4984(13) . ?
C6 C7 1.3729(14) . ?
C6 C5 1.4189(13) . ?
C6 H6 0.9500 . ?
C7 C7 1.412(2) 3_656 ?
C7 H7 0.9500 . ?
C8 C9 1.3895(13) . ?
C8 C13 1.3903(14) . ?
C9 C10 1.3907(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.3873(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3884(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3908(14) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C2 C3 1.3792(12) . ?
C2 C5 1.4155(13) . ?
C3 C3 1.3990(18) 3_656 ?
C3 C4 1.4901(13) . ?
C5 C5 1.4390(19) 3_656 ?
 
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
C1 N1 C4 111.63(8) . . ?
C1 N1 C8 125.03(8) . . ?
C4 N1 C8 123.29(8) . . ?
O1 C1 N1 125.70(9) . . ?
O1 C1 C2 128.39(9) . . ?
N1 C1 C2 105.86(8) . . ?
C7 C6 C5 119.88(10) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C7 120.92(6) . 3_656 ?
C6 C7 H7 119.5 . . ?
C7 C7 H7 119.5 3_656 . ?
C9 C8 C13 121.13(9) . . ?
C9 C8 N1 119.38(9) . . ?
C13 C8 N1 119.46(8) . . ?
C8 C9 C10 119.28(10) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.15(10) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.04(9) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.49(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 118.89(9) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C3 C2 C5 123.28(8) . . ?
C3 C2 C1 107.82(8) . . ?
C5 C2 C1 128.90(8) . . ?
C2 C3 C3 119.19(5) . 3_656 ?
C2 C3 C4 108.86(8) . . ?
C3 C3 C4 131.86(5) 3_656 . ?
O2 C4 N1 125.45(9) . . ?
O2 C4 C3 128.98(9) . . ?
N1 C4 C3 105.48(8) . . ?
C2 C5 C6 123.32(9) . . ?
C2 C5 C5 117.48(5) . 3_656 ?
C6 C5 C5 119.19(6) . 3_656 ?
 
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
C4 N1 C1 O1 -175.76(9) . . . . ?
C8 N1 C1 O1 6.76(16) . . . . ?
C4 N1 C1 C2 1.72(10) . . . . ?
C8 N1 C1 C2 -175.76(8) . . . . ?
C5 C6 C7 C7 0.29(19) . . . 3_656 ?
C1 N1 C8 C9 43.43(14) . . . . ?
C4 N1 C8 C9 -133.76(10) . . . . ?
C1 N1 C8 C13 -138.92(10) . . . . ?
C4 N1 C8 C13 43.88(13) . . . . ?
C13 C8 C9 C10 -0.09(15) . . . . ?
N1 C8 C9 C10 177.51(9) . . . . ?
C8 C9 C10 C11 -1.08(15) . . . . ?
C9 C10 C11 C12 1.10(16) . . . . ?
C10 C11 C12 C13 0.04(16) . . . . ?
C9 C8 C13 C12 1.21(15) . . . . ?
N1 C8 C13 C12 -176.39(9) . . . . ?
C11 C12 C13 C8 -1.19(16) . . . . ?
O1 C1 C2 C3 172.46(10) . . . . ?
N1 C1 C2 C3 -4.93(10) . . . . ?
O1 C1 C2 C5 -7.04(17) . . . . ?
N1 C1 C2 C5 175.57(9) . . . . ?
C5 C2 C3 C3 2.65(16) . . . 3_656 ?
C1 C2 C3 C3 -176.88(10) . . . 3_656 ?
C5 C2 C3 C4 -174.34(8) . . . . ?
C1 C2 C3 C4 6.13(10) . . . . ?
C1 N1 C4 O2 -174.99(10) . . . . ?
C8 N1 C4 O2 2.53(15) . . . . ?
C1 N1 C4 C3 1.86(10) . . . . ?
C8 N1 C4 C3 179.39(8) . . . . ?
C2 C3 C4 O2 171.64(10) . . . . ?
C3 C3 C4 O2 -4.8(2) 3_656 . . . ?
C2 C3 C4 N1 -5.07(10) . . . . ?
C3 C3 C4 N1 178.46(13) 3_656 . . . ?
C3 C2 C5 C6 178.90(9) . . . . ?
C1 C2 C5 C6 -1.67(15) . . . . ?
C3 C2 C5 C5 -0.17(16) . . . 3_656 ?
C1 C2 C5 C5 179.26(10) . . . 3_656 ?
C7 C6 C5 C2 -179.62(9) . . . . ?
C7 C6 C5 C5 -0.58(16) . . . 3_656 ?
 
_refine_diff_density_max    0.428
_refine_diff_density_min   -0.284
_refine_diff_density_rms    0.053



