 
data_A24252O_033
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H22 N2 O3'
_chemical_formula_sum
 'C21 H22 N2 O3' 
_chemical_formula_weight          350.40

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            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'
 
_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, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    27.8530(14)
_cell_length_b                    10.8984(6)
_cell_length_c                    5.9988(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1820.95(16)
_cell_formula_units_Z             4
_cell_measurement_temperature     203(2)
_cell_measurement_reflns_used     7702
_cell_measurement_theta_min       2.88
_cell_measurement_theta_max       27.10
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.278          
_exptl_crystal_F_000              744
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.177
_exptl_crystal_size_mid           0.031
_exptl_crystal_size_min           0.028
_exptl_absorpt_coefficient_mu     0.086
_shelx_estimated_absorpt_T_min    0.985
_shelx_estimated_absorpt_T_max    0.998
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.6677
_exptl_absorpt_correction_T_max   0.7455
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       203(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Ius 3.0 microfocus source'
_diffrn_measurement_device_type   'PHOTON II CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             13100
_diffrn_reflns_av_unetI/netI      0.0615
_diffrn_reflns_av_R_equivalents   0.0882
_diffrn_reflns_limit_h_min        -35
_diffrn_reflns_limit_h_max        35
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          2.882
_diffrn_reflns_theta_max          27.103
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  0.994
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   0.994
_diffrn_reflns_point_group_measured_fraction_max   0.958
_diffrn_reflns_point_group_measured_fraction_full  0.974
_reflns_number_total              3841
_reflns_number_gt                 3133
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.760
_reflns_Friedel_fraction_max      0.917
_reflns_Friedel_fraction_full     0.950
 
_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 software' 
_computing_cell_refinement        'Bruker APEX5 software' 
_computing_data_reduction         'Bruker APEX5 software' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0194P)²+0.2793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_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_abs_structure_details
;
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.1(10)
_chemical_absolute_configuration  .
_refine_ls_number_reflns          3841
_refine_ls_number_parameters      236
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0640
_refine_ls_R_factor_gt            0.0458
_refine_ls_wR_factor_ref          0.0879
_refine_ls_wR_factor_gt           0.0815
_refine_ls_goodness_of_fit_ref    1.087
_refine_ls_restrained_S_all       1.087
_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 0.65051(8) 0.2869(2) 0.3730(4) 0.0491(6) Uani 1 1 d . . . . .
C2 C 0.66286(10) 0.3279(2) 0.5499(5) 0.0311(7) Uani 1 1 d . . . . .
C3 C 0.70732(10) 0.3023(2) 0.6798(5) 0.0278(6) Uani 1 1 d . . . . .
C4 C 0.74510(11) 0.2243(3) 0.6335(6) 0.0383(7) Uani 1 1 d . . . . .
H4 H 0.745580 0.175144 0.502649 0.046 Uiso 1 1 calc R U . . .
C5 C 0.78248(11) 0.2210(3) 0.7876(6) 0.0447(8) Uani 1 1 d . . . . .
H5 H 0.808989 0.168052 0.761594 0.054 Uiso 1 1 calc R U . . .
C6 C 0.78196(11) 0.2927(3) 0.9770(7) 0.0434(8) Uani 1 1 d . . . . .
H6 H 0.808117 0.288717 1.078404 0.052 Uiso 1 1 calc R U . . .
C7 C 0.74370(10) 0.3706(3) 1.0214(5) 0.0361(7) Uani 1 1 d . . . . .
H7 H 0.743127 0.420108 1.151759 0.043 Uiso 1 1 calc R U . . .
C8 C 0.70656(9) 0.3737(2) 0.8695(5) 0.0282(6) Uani 1 1 d . . . . .
C9 C 0.66126(10) 0.4457(2) 0.8684(6) 0.0318(6) Uani 1 1 d . . . . .
O10 O 0.64698(9) 0.5194(2) 1.0050(4) 0.0525(6) Uani 1 1 d . . . . .
N11 N 0.63728(8) 0.4138(2) 0.6746(4) 0.0311(5) Uani 1 1 d . . . . .
C12 C 0.58989(10) 0.4597(3) 0.6114(7) 0.0404(8) Uani 1 1 d . . . . .
H12A H 0.569728 0.466127 0.746825 0.049 Uiso 1 1 calc R U . . .
H12B H 0.574504 0.399805 0.510083 0.049 Uiso 1 1 calc R U . . .
C13 C 0.59145(9) 0.5842(2) 0.4970(5) 0.0300(6) Uani 1 1 d . . . . .
H13A H 0.616620 0.583311 0.380521 0.036 Uiso 1 1 calc R U . . .
H13B H 0.600070 0.647912 0.607626 0.036 Uiso 1 1 calc R U . . .
C14 C 0.54330(9) 0.6166(2) 0.3910(6) 0.0320(6) Uani 1 1 d . . . . .
H14A H 0.536004 0.556734 0.271538 0.038 Uiso 1 1 calc R U . . .
H14B H 0.517699 0.610526 0.504923 0.038 Uiso 1 1 calc R U . . .
C15 C 0.54348(9) 0.7454(2) 0.2933(5) 0.0259(6) Uani 1 1 d . . . . .
H15 H 0.545630 0.808439 0.414021 0.031 Uiso 1 1 calc R U . . .
C16 C 0.57946(10) 0.7736(3) 0.1052(6) 0.0365(7) Uani 1 1 d . . . . .
H16A H 0.605380 0.830944 0.148589 0.044 Uiso 1 1 calc R U . . .
H16B H 0.592578 0.699705 0.030952 0.044 Uiso 1 1 calc R U . . .
C17 C 0.53794(10) 0.8342(3) -0.0206(5) 0.0354(7) Uani 1 1 d . . . . .
H17A H 0.538070 0.924894 -0.012113 0.042 Uiso 1 1 calc R U . . .
H17B H 0.534630 0.806007 -0.176706 0.042 Uiso 1 1 calc R U . . .
N18 N 0.50383(8) 0.77533(19) 0.1351(4) 0.0263(5) Uani 1 1 d . . . . .
C19 C 0.46178(10) 0.8346(2) 0.2006(5) 0.0252(6) Uani 1 1 d . . . . .
C20 C 0.43899(10) 0.9173(2) 0.0559(5) 0.0290(6) Uani 1 1 d . . . . .
H20 H 0.453260 0.935964 -0.083902 0.035 Uiso 1 1 calc R U . . .
C21 C 0.39605(10) 0.9719(2) 0.1144(5) 0.0308(6) Uani 1 1 d . . . . .
H21 H 0.381274 1.028305 0.015125 0.037 Uiso 1 1 calc R U . . .
C22 C 0.37421(10) 0.9451(2) 0.3171(5) 0.0285(6) Uani 1 1 d . . . . .
C23 C 0.39638(10) 0.8642(2) 0.4629(5) 0.0292(6) Uani 1 1 d . . . . .
H23 H 0.381972 0.845740 0.602459 0.035 Uiso 1 1 calc R U . . .
C24 C 0.43975(9) 0.8101(2) 0.4039(5) 0.0285(6) Uani 1 1 d . . . . .
H24 H 0.454729 0.755034 0.505065 0.034 Uiso 1 1 calc R U . . .
O25 O 0.33108(6) 1.00278(19) 0.3583(4) 0.0377(5) Uani 1 1 d . . . . .
C26 C 0.30746(11) 0.9705(3) 0.5585(6) 0.0391(7) Uani 1 1 d . . . . .
H26A H 0.276727 1.013994 0.567565 0.059 Uiso 1 1 calc R U . . .
H26B H 0.327583 0.993378 0.685925 0.059 Uiso 1 1 calc R U . . .
H26C H 0.301710 0.881813 0.560801 0.059 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 C2 1.201(4) . ?
C2 N11 1.394(4) . ?
C2 C3 1.489(4) . ?
C3 C8 1.379(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.486(4) . ?
C9 O10 1.214(4) . ?
C9 N11 1.385(4) . ?
N11 C12 1.462(4) . ?
C12 C13 1.520(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N18 1.492(4) . ?
C15 C16 1.540(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.530(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N18 1.479(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N18 C19 1.394(4) . ?
C19 C24 1.391(4) . ?
C19 C20 1.403(4) . ?
C20 C21 1.381(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?
C22 O25 1.378(3) . ?
C22 C23 1.387(4) . ?
C23 C24 1.390(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O25 C26 1.414(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
 
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 C2 N11 125.2(3) . . ?
O1 C2 C3 129.1(3) . . ?
N11 C2 C3 105.7(2) . . ?
C8 C3 C4 121.7(3) . . ?
C8 C3 C2 108.3(2) . . ?
C4 C3 C2 130.1(3) . . ?
C3 C4 C5 116.9(3) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C3 C8 C7 121.4(3) . . ?
C3 C8 C9 107.9(3) . . ?
C7 C8 C9 130.7(3) . . ?
O10 C9 N11 125.1(3) . . ?
O10 C9 C8 128.6(3) . . ?
N11 C9 C8 106.3(2) . . ?
C9 N11 C2 111.9(2) . . ?
C9 N11 C12 124.5(3) . . ?
C2 N11 C12 123.6(3) . . ?
N11 C12 C13 113.4(2) . . ?
N11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 111.7(2) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 111.8(2) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N18 C15 C14 116.4(2) . . ?
N18 C15 C16 88.4(2) . . ?
C14 C15 C16 117.9(2) . . ?
N18 C15 H15 110.8 . . ?
C14 C15 H15 110.8 . . ?
C16 C15 H15 110.8 . . ?
C17 C16 C15 87.5(2) . . ?
C17 C16 H16A 114.1 . . ?
C15 C16 H16A 114.1 . . ?
C17 C16 H16B 114.1 . . ?
C15 C16 H16B 114.1 . . ?
H16A C16 H16B 111.3 . . ?
N18 C17 C16 89.3(2) . . ?
N18 C17 H17A 113.8 . . ?
C16 C17 H17A 113.8 . . ?
N18 C17 H17B 113.8 . . ?
C16 C17 H17B 113.8 . . ?
H17A C17 H17B 111.0 . . ?
C19 N18 C17 121.1(2) . . ?
C19 N18 C15 123.0(2) . . ?
C17 N18 C15 91.2(2) . . ?
C24 C19 N18 121.9(2) . . ?
C24 C19 C20 117.8(2) . . ?
N18 C19 C20 120.2(3) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
O25 C22 C23 124.4(3) . . ?
O25 C22 C21 116.3(2) . . ?
C23 C22 C21 119.3(2) . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 121.7(3) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
C22 O25 C26 116.4(2) . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
 
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
O1 C2 C3 C8 178.0(3) . . . . ?
N11 C2 C3 C8 -0.9(3) . . . . ?
O1 C2 C3 C4 -1.2(5) . . . . ?
N11 C2 C3 C4 179.9(3) . . . . ?
C8 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C5 179.2(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C4 C3 C8 C7 0.2(4) . . . . ?
C2 C3 C8 C7 -179.1(3) . . . . ?
C4 C3 C8 C9 -179.8(3) . . . . ?
C2 C3 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C3 -0.2(4) . . . . ?
C6 C7 C8 C9 179.9(3) . . . . ?
C3 C8 C9 O10 -179.8(3) . . . . ?
C7 C8 C9 O10 0.1(5) . . . . ?
C3 C8 C9 N11 -0.5(3) . . . . ?
C7 C8 C9 N11 179.5(3) . . . . ?
O10 C9 N11 C2 179.3(3) . . . . ?
C8 C9 N11 C2 -0.1(3) . . . . ?
O10 C9 N11 C12 -3.3(5) . . . . ?
C8 C9 N11 C12 177.4(2) . . . . ?
O1 C2 N11 C9 -178.4(3) . . . . ?
C3 C2 N11 C9 0.6(3) . . . . ?
O1 C2 N11 C12 4.1(4) . . . . ?
C3 C2 N11 C12 -176.9(2) . . . . ?
C9 N11 C12 C13 83.6(4) . . . . ?
C2 N11 C12 C13 -99.3(3) . . . . ?
N11 C12 C13 C14 168.0(3) . . . . ?
C12 C13 C14 C15 175.2(3) . . . . ?
C13 C14 C15 N18 164.4(2) . . . . ?
C13 C14 C15 C16 61.3(3) . . . . ?
N18 C15 C16 C17 14.2(2) . . . . ?
C14 C15 C16 C17 133.4(3) . . . . ?
C15 C16 C17 N18 -14.3(2) . . . . ?
C16 C17 N18 C19 145.2(3) . . . . ?
C16 C17 N18 C15 14.8(2) . . . . ?
C14 C15 N18 C19 95.7(3) . . . . ?
C16 C15 N18 C19 -143.7(2) . . . . ?
C14 C15 N18 C17 -135.3(3) . . . . ?
C16 C15 N18 C17 -14.7(2) . . . . ?
C17 N18 C19 C24 -152.9(3) . . . . ?
C15 N18 C19 C24 -38.1(4) . . . . ?
C17 N18 C19 C20 30.3(4) . . . . ?
C15 N18 C19 C20 145.1(2) . . . . ?
C24 C19 C20 C21 -0.2(4) . . . . ?
N18 C19 C20 C21 176.7(2) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 O25 -179.0(2) . . . . ?
C20 C21 C22 C23 1.0(4) . . . . ?
O25 C22 C23 C24 179.4(3) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
N18 C19 C24 C23 -176.2(3) . . . . ?
C20 C19 C24 C23 0.6(4) . . . . ?
C23 C22 O25 C26 -3.4(4) . . . . ?
C21 C22 O25 C26 176.5(3) . . . . ?
 
_refine_diff_density_max    0.148
_refine_diff_density_min   -0.181
_refine_diff_density_rms    0.040



