 
data_1064Ext_0m_a
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety         'C22 H21 N O4'
_chemical_formula_sum
 'C22 H21 N O4' 
_chemical_formula_weight          363.40
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       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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'
 
_cell_length_a                    8.4612(3)
_cell_length_b                    10.1109(4)
_cell_length_c                    11.2954(4)
_cell_angle_alpha                 98.813(2)
_cell_angle_beta                  93.138(2)
_cell_angle_gamma                 95.520(2)
_cell_volume                      948.11(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9608
_cell_measurement_theta_min        2.52
_cell_measurement_theta_max       26.44
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.273          
_exptl_crystal_F_000              418
_exptl_transmission_factor_min    0.751
_exptl_transmission_factor_max    0.845
_exptl_crystal_size_max           0.143
_exptl_crystal_size_mid           0.085
_exptl_crystal_size_min           0.024
_exptl_absorpt_coefficient_mu     0.088
_shelx_estimated_absorpt_T_min    0.785
_shelx_estimated_absorpt_T_max    0.896
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14141
_diffrn_reflns_av_unetI/netI      0.0269
_diffrn_reflns_av_R_equivalents   0.0314
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.958
_diffrn_reflns_theta_max          26.458
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.995
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.995
_diffrn_reflns_point_group_measured_fraction_max   0.993
_diffrn_reflns_point_group_measured_fraction_full  0.995
_reflns_number_total              3894
_reflns_number_gt                 3180
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1000P)²+0.8241P] 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          3894
_refine_ls_number_parameters      247
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0559
_refine_ls_R_factor_gt            0.0459
_refine_ls_wR_factor_ref          0.1343
_refine_ls_wR_factor_gt           0.1205
_refine_ls_goodness_of_fit_ref    0.669
_refine_ls_restrained_S_all       0.669
_refine_ls_shift/su_max           0.004
_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
O4 O 0.82460(14) 0.58843(11) 0.28936(10) 0.0477(3) Uani 1 1 d . . . . .
O3 O 0.94177(15) 0.76738(12) 0.22022(10) 0.0527(3) Uani 1 1 d . . . . .
O1 O 1.13316(15) 0.73341(13) 0.63195(11) 0.0570(3) Uani 1 1 d . . . . .
O2 O 1.10118(14) 0.65778(13) 0.43503(11) 0.0532(3) Uani 1 1 d . . . . .
N1 N 0.72523(15) 0.88644(12) 0.39919(11) 0.0375(3) Uani 1 1 d . . . . .
C5 C 0.83860(16) 0.79981(13) 0.41334(12) 0.0329(3) Uani 1 1 d . . . . .
C4 C 0.92041(16) 0.80239(14) 0.52048(12) 0.0338(3) Uani 1 1 d . . . . .
C21 C 0.87637(17) 0.71806(15) 0.29665(13) 0.0376(3) Uani 1 1 d . . . . .
C1 C 0.71190(17) 0.99202(14) 0.49395(13) 0.0373(3) Uani 1 1 d . . . . .
H1 H 0.649148 1.059542 0.480283 0.045 Uiso 1 1 calc R U . . .
C2 C 0.78467(18) 0.99892(14) 0.60098(13) 0.0376(3) Uani 1 1 d . . . . .
H2 H 0.777846 1.074325 0.658281 0.045 Uiso 1 1 calc R U . . .
C19 C 1.05963(17) 0.72907(15) 0.53635(14) 0.0387(3) Uani 1 1 d . . . . .
C3 C 0.87861(17) 0.88921(14) 0.63415(12) 0.0364(3) Uani 1 1 d . . . . .
H3 H 0.977974 0.931490 0.678585 0.044 Uiso 1 1 calc R U . . .
C6 C 0.78641(19) 0.80691(15) 0.71557(13) 0.0392(3) Uani 1 1 d . . . . .
C13 C 0.59027(18) 0.97541(15) 0.23730(13) 0.0393(3) Uani 1 1 d . . . . .
H13 H 0.655892 1.055852 0.257900 0.047 Uiso 1 1 calc R U . . .
C12 C 0.61216(17) 0.86808(14) 0.29733(12) 0.0357(3) Uani 1 1 d . . . . .
C14 C 0.47036(19) 0.96237(16) 0.14658(13) 0.0424(3) Uani 1 1 d . . . . .
H14 H 0.455009 1.035303 0.107705 0.051 Uiso 1 1 calc R U . . .
C17 C 0.51701(19) 0.74746(16) 0.26378(15) 0.0441(4) Uani 1 1 d . . . . .
H17 H 0.531775 0.674831 0.303199 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6381(2) 0.73897(17) 0.67676(15) 0.0489(4) Uani 1 1 d . . . . .
H11 H 0.596151 0.741299 0.599340 0.059 Uiso 1 1 calc R U . . .
C15 C 0.37242(19) 0.84259(17) 0.11237(13) 0.0444(4) Uani 1 1 d . . . . .
C16 C 0.3996(2) 0.73545(17) 0.17107(15) 0.0492(4) Uani 1 1 d . . . . .
H16 H 0.337572 0.653533 0.147784 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2382(2) 0.8320(2) 0.01697(17) 0.0645(5) Uani 1 1 d . . . . .
H18A H 0.195219 0.916899 0.021348 0.097 Uiso 1 1 calc R U . . .
H18B H 0.156405 0.763932 0.029497 0.097 Uiso 1 1 calc R U . . .
H18C H 0.277603 0.808286 -0.060738 0.097 Uiso 1 1 calc R U . . .
C7 C 0.8459(3) 0.8019(2) 0.83155(16) 0.0622(5) Uani 1 1 d . . . . .
H7 H 0.945387 0.846302 0.859623 0.075 Uiso 1 1 calc R U . . .
C22 C 0.8693(3) 0.5012(2) 0.18588(18) 0.0726(6) Uani 1 1 d . . . . .
H22A H 0.810241 0.516799 0.115213 0.109 Uiso 1 1 calc R U . . .
H22B H 0.846155 0.409029 0.196299 0.109 Uiso 1 1 calc R U . . .
H22C H 0.981117 0.519747 0.177316 0.109 Uiso 1 1 calc R U . . .
C20 C 1.2287(2) 0.5760(2) 0.4465(2) 0.0642(5) Uani 1 1 d . . . . .
H20A H 1.325590 0.632741 0.473391 0.096 Uiso 1 1 calc R U . . .
H20B H 1.241312 0.523315 0.369999 0.096 Uiso 1 1 calc R U . . .
H20C H 1.204787 0.517241 0.503750 0.096 Uiso 1 1 calc R U . . .
C10 C 0.5510(3) 0.6676(2) 0.7512(2) 0.0665(6) Uani 1 1 d . . . . .
H10 H 0.451730 0.622463 0.723590 0.080 Uiso 1 1 calc R U . . .
C9 C 0.6115(4) 0.6636(2) 0.8659(2) 0.0802(7) Uani 1 1 d . . . . .
H9 H 0.553578 0.615680 0.916000 0.096 Uiso 1 1 calc R U . . .
C8 C 0.7577(4) 0.7307(3) 0.9060(2) 0.0835(8) Uani 1 1 d . . . . .
H8 H 0.798239 0.728647 0.983820 0.100 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
O4 C21 1.3301(18) . ?
O4 C22 1.443(2) . ?
O3 C21 1.1964(18) . ?
O1 C19 1.2091(19) . ?
O2 C19 1.3390(19) . ?
O2 C20 1.433(2) . ?
N1 C5 1.3787(18) . ?
N1 C1 1.4086(18) . ?
N1 C12 1.4329(18) . ?
C5 C4 1.3563(19) . ?
C5 C21 1.5118(19) . ?
C4 C19 1.468(2) . ?
C4 C3 1.5192(19) . ?
C1 C2 1.315(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.506(2) . ?
C2 H2 0.9300 . ?
C3 C6 1.528(2) . ?
C3 H3 0.9800 . ?
C6 C11 1.386(2) . ?
C6 C7 1.388(2) . ?
C13 C14 1.384(2) . ?
C13 C12 1.386(2) . ?
C13 H13 0.9300 . ?
C12 C17 1.384(2) . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C17 C16 1.387(2) . ?
C17 H17 0.9300 . ?
C11 C10 1.386(2) . ?
C11 H11 0.9300 . ?
C15 C16 1.385(2) . ?
C15 C18 1.506(2) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C10 C9 1.374(3) . ?
C10 H10 0.9300 . ?
C9 C8 1.370(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
 
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
C21 O4 C22 115.45(13) . . ?
C19 O2 C20 116.77(14) . . ?
C5 N1 C1 118.20(12) . . ?
C5 N1 C12 123.27(12) . . ?
C1 N1 C12 118.33(11) . . ?
C4 C5 N1 121.70(12) . . ?
C4 C5 C21 124.25(13) . . ?
N1 C5 C21 113.55(12) . . ?
C5 C4 C19 123.92(13) . . ?
C5 C4 C3 121.65(12) . . ?
C19 C4 C3 114.35(12) . . ?
O3 C21 O4 125.29(14) . . ?
O3 C21 C5 122.72(14) . . ?
O4 C21 C5 111.96(12) . . ?
C2 C1 N1 122.62(13) . . ?
C2 C1 H1 118.7 . . ?
N1 C1 H1 118.7 . . ?
C1 C2 C3 122.41(13) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
O1 C19 O2 122.17(14) . . ?
O1 C19 C4 123.48(14) . . ?
O2 C19 C4 114.35(13) . . ?
C2 C3 C4 109.39(11) . . ?
C2 C3 C6 110.56(12) . . ?
C4 C3 C6 112.18(12) . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C6 C3 H3 108.2 . . ?
C11 C6 C7 118.17(16) . . ?
C11 C6 C3 120.69(13) . . ?
C7 C6 C3 121.11(16) . . ?
C14 C13 C12 119.73(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C17 C12 C13 119.76(14) . . ?
C17 C12 N1 120.61(13) . . ?
C13 C12 N1 119.47(13) . . ?
C13 C14 C15 121.39(14) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C12 C17 C16 119.66(14) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C10 C11 C6 121.22(18) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C16 C15 C14 117.88(14) . . ?
C16 C15 C18 121.45(16) . . ?
C14 C15 C18 120.65(16) . . ?
C15 C16 C17 121.53(15) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C8 C9 C10 119.68(19) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
 
_refine_diff_density_max    0.175
_refine_diff_density_min   -0.195
_refine_diff_density_rms    0.041



