 
data_benhay1_0m
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H22 N2 O4' 
_chemical_formula_weight          354.39

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   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            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_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'
 
_cell_length_a                    12.2554(3)
_cell_length_b                    4.96200(10)
_cell_length_c                    15.2826(3)
_cell_angle_alpha                 90
_cell_angle_beta                  109.7830(10)
_cell_angle_gamma                 90
_cell_volume                      874.51(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     104(2)
_cell_measurement_reflns_used     5838 
_cell_measurement_theta_min       3.073 
_cell_measurement_theta_max       68.043 
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.346          
_exptl_crystal_F_000              376
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.160
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.020
_exptl_absorpt_coefficient_mu     0.772
_shelx_estimated_absorpt_T_min    0.886
_shelx_estimated_absorpt_T_max    0.985
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.886
_exptl_absorpt_correction_T_max   0.985
_exptl_absorpt_process_details    'Bruker Sadabs'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       104(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'microfocus sealed tube'  
_diffrn_measurement_device_type   'Bruker X8 Prospector Ultra' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14579
_diffrn_reflns_av_unetI/netI      0.0588
_diffrn_reflns_av_R_equivalents   0.1008
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -5
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.073
_diffrn_reflns_theta_max          70.245
_diffrn_reflns_theta_full         68.000
_diffrn_measured_fraction_theta_max   0.955
_diffrn_measured_fraction_theta_full  0.980
_diffrn_reflns_Laue_measured_fraction_max    0.955
_diffrn_reflns_Laue_measured_fraction_full   0.980
_diffrn_reflns_point_group_measured_fraction_max   0.957
_diffrn_reflns_point_group_measured_fraction_full  0.983
_reflns_number_total              2944
_reflns_number_gt                 2582
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.782
_reflns_Friedel_fraction_max      0.959
_reflns_Friedel_fraction_full     0.986
 
_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 APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details
;
 Refined as a 2-component inversion 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)+(0.0640P)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_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.0(3)
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          2944
_refine_ls_number_parameters      242
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0519
_refine_ls_R_factor_gt            0.0439
_refine_ls_wR_factor_ref          0.1092
_refine_ls_wR_factor_gt           0.1059
_refine_ls_goodness_of_fit_ref    1.075
_refine_ls_restrained_S_all       1.075
_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 0.07548(19) 1.0709(4) 1.04778(15) 0.0182(5) Uani 1 1 d . . . . .
N1 N 0.1499(2) 0.9507(5) 0.93354(18) 0.0129(6) Uani 1 1 d . . . . .
C1 C 0.1358(3) 0.9260(6) 1.0180(2) 0.0139(7) Uani 1 1 d . . . . .
O2 O 0.4057(2) 0.5052(5) 0.78983(16) 0.0228(6) Uani 1 1 d . . . . .
N2 N 0.3970(3) 0.6375(6) 1.3259(2) 0.0211(7) Uani 1 1 d . . . . .
H2N H 0.396(4) 0.822(11) 1.336(3) 0.048(13) Uiso 1 1 d . . . . .
C2 C 0.2112(3) 0.6909(6) 1.0702(2) 0.0135(7) Uani 1 1 d . . . . .
H2A H 0.1596 0.5385 1.0740 0.016 Uiso 1 1 calc R U . . .
O3 O -0.1664(2) 0.8408(6) 0.49816(16) 0.0299(7) Uani 1 1 d . . . . .
C3 C 0.2755(3) 0.6127(6) 1.0056(2) 0.0129(7) Uani 1 1 d . . . . .
O4 O 0.4279(2) 0.2135(5) 1.38668(15) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.3573(3) 0.4151(6) 1.0092(2) 0.0151(7) Uani 1 1 d . . . . .
H4A H 0.3846 0.3000 1.0618 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3989(3) 0.3863(7) 0.9359(2) 0.0161(7) Uani 1 1 d . . . . .
H5A H 0.4549 0.2514 0.9386 0.019 Uiso 1 1 calc R U . . .
C6 C 0.3592(3) 0.5536(7) 0.8583(2) 0.0153(7) Uani 1 1 d . . . . .
C7 C 0.2764(3) 0.7514(6) 0.8521(2) 0.0145(7) Uani 1 1 d . . . . .
H7A H 0.2489 0.8662 0.7995 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2359(3) 0.7738(6) 0.9262(2) 0.0117(7) Uani 1 1 d . . . . .
C9 C 0.0956(3) 1.1631(6) 0.8659(2) 0.0139(7) Uani 1 1 d . . . . .
H9A H 0.1569 1.2857 0.8608 0.017 Uiso 1 1 calc R U . . .
H9B H 0.0432 1.2698 0.8896 0.017 Uiso 1 1 calc R U . . .
C10 C 0.0271(3) 1.0584(7) 0.7700(2) 0.0136(7) Uani 1 1 d . . . . .
C11 C -0.0544(3) 0.8546(7) 0.7553(2) 0.0178(7) Uani 1 1 d . . . . .
H11A H -0.0655 0.7692 0.8073 0.021 Uiso 1 1 calc R U . . .
C12 C -0.1205(3) 0.7720(7) 0.6660(2) 0.0207(8) Uani 1 1 d . . . . .
H12A H -0.1758 0.6314 0.6572 0.025 Uiso 1 1 calc R U . . .
C13 C -0.1048(3) 0.8968(7) 0.5900(2) 0.0207(8) Uani 1 1 d . . . . .
C14 C -0.0214(3) 1.0974(8) 0.6035(2) 0.0244(8) Uani 1 1 d . . . . .
H14A H -0.0086 1.1797 0.5516 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0427(3) 1.1759(7) 0.6928(2) 0.0194(8) Uani 1 1 d . . . . .
H15A H 0.0991 1.3142 0.7016 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3623(3) 0.6667(8) 0.7077(2) 0.0253(9) Uani 1 1 d . . . . .
H16A H 0.4038 0.6212 0.6650 0.038 Uiso 1 1 calc R U . . .
H16B H 0.3742 0.8577 0.7246 0.038 Uiso 1 1 calc R U . . .
H16C H 0.2793 0.6317 0.6774 0.038 Uiso 1 1 calc R U . . .
C17 C -0.2466(3) 0.6218(9) 0.4799(3) 0.0330(10) Uani 1 1 d . . . . .
H17A H -0.2861 0.6050 0.4127 0.050 Uiso 1 1 calc R U . . .
H17B H -0.3039 0.6556 0.5104 0.050 Uiso 1 1 calc R U . . .
H17C H -0.2047 0.4546 0.5041 0.050 Uiso 1 1 calc R U . . .
C18 C 0.2826(3) 0.7798(6) 1.1689(2) 0.0185(8) Uani 1 1 d . . . . .
H18A H 0.3397 0.9172 1.1655 0.022 Uiso 1 1 calc R U . . .
H18B H 0.2304 0.8648 1.1981 0.022 Uiso 1 1 calc R U . . .
C19 C 0.3462(3) 0.5492(7) 1.2292(2) 0.0210(8) Uani 1 1 d . . . . .
H19A H 0.2916 0.3988 1.2252 0.025 Uiso 1 1 calc R U . . .
H19C H 0.4082 0.4834 1.2067 0.025 Uiso 1 1 calc R U . . .
C20 C 0.4315(3) 0.4618(8) 1.3956(2) 0.0190(8) Uani 1 1 d . . . . .
H20A H 0.4613 0.5321 1.4569 0.023 Uiso 1 1 calc R U . . .
 
 
_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 1.224(4) . ?
N1 C1 1.364(4) . ?
N1 C8 1.405(4) . ?
N1 C9 1.469(4) . ?
C1 C2 1.534(4) . ?
O2 C6 1.371(4) . ?
O2 C16 1.431(4) . ?
N2 C20 1.330(4) . ?
N2 C19 1.463(4) . ?
N2 H2N 0.93(6) . ?
C2 C3 1.508(4) . ?
C2 C18 1.530(4) . ?
C2 H2A 1.0000 . ?
O3 C13 1.379(4) . ?
O3 C17 1.427(5) . ?
C3 C4 1.389(4) . ?
C3 C8 1.395(4) . ?
O4 C20 1.239(4) . ?
C4 C5 1.387(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.391(5) . ?
C7 C8 1.387(4) . ?
C7 H7A 0.9500 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.385(5) . ?
C10 C15 1.387(5) . ?
C11 C12 1.393(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.386(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.391(5) . ?
C14 C15 1.381(5) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.510(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19C 0.9900 . ?
C20 H20A 0.9500 . ?
 
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 C8 110.9(3) . . ?
C1 N1 C9 123.9(3) . . ?
C8 N1 C9 124.5(2) . . ?
O1 C1 N1 125.8(3) . . ?
O1 C1 C2 125.9(3) . . ?
N1 C1 C2 108.3(3) . . ?
C6 O2 C16 116.4(2) . . ?
C20 N2 C19 121.6(3) . . ?
C20 N2 H2N 122(3) . . ?
C19 N2 H2N 116(3) . . ?
C3 C2 C18 117.9(3) . . ?
C3 C2 C1 102.2(2) . . ?
C18 C2 C1 109.7(3) . . ?
C3 C2 H2A 108.9 . . ?
C18 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C13 O3 C17 117.2(3) . . ?
C4 C3 C8 118.2(3) . . ?
C4 C3 C2 133.3(3) . . ?
C8 C3 C2 108.4(3) . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
O2 C6 C7 123.6(3) . . ?
O2 C6 C5 115.4(3) . . ?
C7 C6 C5 121.0(3) . . ?
C8 C7 C6 117.1(3) . . ?
C8 C7 H7A 121.5 . . ?
C6 C7 H7A 121.5 . . ?
C7 C8 C3 123.3(3) . . ?
C7 C8 N1 126.9(3) . . ?
C3 C8 N1 109.8(2) . . ?
N1 C9 C10 113.9(3) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C15 117.9(3) . . ?
C11 C10 C9 122.8(3) . . ?
C15 C10 C9 119.2(3) . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11A 119.2 . . ?
C12 C11 H11A 119.2 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
O3 C13 C12 125.4(3) . . ?
O3 C13 C14 114.7(3) . . ?
C12 C13 C14 120.0(3) . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
C14 C15 C10 121.8(3) . . ?
C14 C15 H15A 119.1 . . ?
C10 C15 H15A 119.1 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C2 112.8(3) . . ?
C19 C18 H18A 109.0 . . ?
C2 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C2 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N2 C19 C18 110.2(3) . . ?
N2 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
N2 C19 H19C 109.6 . . ?
C18 C19 H19C 109.6 . . ?
H19A C19 H19C 108.1 . . ?
O4 C20 N2 125.0(3) . . ?
O4 C20 H20A 117.5 . . ?
N2 C20 H20A 117.5 . . ?
 
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
C8 N1 C1 O1 172.6(3) . . . . ?
C9 N1 C1 O1 1.6(5) . . . . ?
C8 N1 C1 C2 -5.8(3) . . . . ?
C9 N1 C1 C2 -176.9(3) . . . . ?
O1 C1 C2 C3 -173.2(3) . . . . ?
N1 C1 C2 C3 5.2(3) . . . . ?
O1 C1 C2 C18 -47.4(4) . . . . ?
N1 C1 C2 C18 131.1(3) . . . . ?
C18 C2 C3 C4 60.1(5) . . . . ?
C1 C2 C3 C4 -179.6(3) . . . . ?
C18 C2 C3 C8 -123.1(3) . . . . ?
C1 C2 C3 C8 -2.9(3) . . . . ?
C8 C3 C4 C5 1.3(4) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C16 O2 C6 C7 -1.6(4) . . . . ?
C16 O2 C6 C5 177.3(3) . . . . ?
C4 C5 C6 O2 -179.5(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
O2 C6 C7 C8 178.9(3) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 C3 1.2(4) . . . . ?
C6 C7 C8 N1 -177.4(3) . . . . ?
C4 C3 C8 C7 -1.9(4) . . . . ?
C2 C3 C8 C7 -179.2(3) . . . . ?
C4 C3 C8 N1 176.9(3) . . . . ?
C2 C3 C8 N1 -0.4(3) . . . . ?
C1 N1 C8 C7 -177.2(3) . . . . ?
C9 N1 C8 C7 -6.2(5) . . . . ?
C1 N1 C8 C3 4.0(3) . . . . ?
C9 N1 C8 C3 175.0(3) . . . . ?
C1 N1 C9 C10 -126.6(3) . . . . ?
C8 N1 C9 C10 63.5(4) . . . . ?
N1 C9 C10 C11 49.5(4) . . . . ?
N1 C9 C10 C15 -132.9(3) . . . . ?
C15 C10 C11 C12 -1.1(5) . . . . ?
C9 C10 C11 C12 176.6(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C17 O3 C13 C12 -5.3(5) . . . . ?
C17 O3 C13 C14 175.0(3) . . . . ?
C11 C12 C13 O3 -178.0(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
O3 C13 C14 C15 177.8(3) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C11 C10 C15 C14 0.9(5) . . . . ?
C9 C10 C15 C14 -176.9(3) . . . . ?
C3 C2 C18 C19 -71.9(4) . . . . ?
C1 C2 C18 C19 171.8(3) . . . . ?
C20 N2 C19 C18 162.8(3) . . . . ?
C2 C18 C19 N2 -170.8(3) . . . . ?
C19 N2 C20 O4 2.2(6) . . . . ?
 
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 
N2 H2N O4  0.93(6) 2.08(5) 2.989(4) 167(4) 1_565
 
_refine_diff_density_max    0.213
_refine_diff_density_min   -0.185
_refine_diff_density_rms    0.048



