 
data_MA3_280922_0m_a
 
_audit_creation_method            'SHELXL-2019/1'
_shelx_SHELXL_version_number      '2019/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H16 N2 O6'
_chemical_formula_sum
 'C18 H16 N2 O6' 
_chemical_formula_weight          356.33

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                    5.4243(6)
_cell_length_b                    8.3905(10)
_cell_length_c                    9.2803(11)
_cell_angle_alpha                 84.202(4)
_cell_angle_beta                  84.144(4)
_cell_angle_gamma                 75.208(4)
_cell_volume                      405.01(8)
_cell_formula_units_Z             1
_cell_measurement_temperature     302(2)
_cell_measurement_reflns_used      7937
_cell_measurement_theta_min        3.22
_cell_measurement_theta_max       26.34

_exptl_crystal_description       'block'
_exptl_crystal_colour            'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.461          
_exptl_crystal_F_000              186
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.270
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.100
_exptl_absorpt_coefficient_mu     0.111
_shelx_estimated_absorpt_T_min    0.971
_shelx_estimated_absorpt_T_max    0.989
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.7004
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       302(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'i-mu-s microfocus source'
_diffrn_measurement_device_type   
 'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14437
_diffrn_reflns_av_unetI/netI      0.0180
_diffrn_reflns_av_R_equivalents   0.0319
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.221
_diffrn_reflns_theta_max          26.426
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.990
_diffrn_measured_fraction_theta_full  0.990
_diffrn_reflns_Laue_measured_fraction_max    0.990
_diffrn_reflns_Laue_measured_fraction_full   0.990
_diffrn_reflns_point_group_measured_fraction_max   0.990
_diffrn_reflns_point_group_measured_fraction_full  0.990
_reflns_number_total              1646
_reflns_number_gt                 1439
_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 APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution     'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0475P)²+0.1151P] 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          1646
_refine_ls_number_parameters      119
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0438
_refine_ls_R_factor_gt            0.0381
_refine_ls_wR_factor_ref          0.1029
_refine_ls_wR_factor_gt           0.0980
_refine_ls_goodness_of_fit_ref    1.039
_refine_ls_restrained_S_all       1.039
_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 0.18682(19) 0.62875(11) 0.11605(11) 0.0470(3) Uani 1 1 d . . . . .
O2 O 1.0341(2) 0.29205(12) 0.55821(11) 0.0498(3) Uani 1 1 d . . . . .
O3 O 0.5049(2) 0.69320(12) 0.21269(12) 0.0512(3) Uani 1 1 d . . . . .
N1 N 0.7861(2) 0.45539(13) 0.38636(12) 0.0369(3) Uani 1 1 d . . . . .
H1 H 0.748774 0.555533 0.348284 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4716(2) 0.41194(15) 0.23643(13) 0.0335(3) Uani 1 1 d . . . . .
C2 C 0.3483(3) 0.30442(17) 0.18558(16) 0.0426(3) Uani 1 1 d . . . . .
H2 H 0.221603 0.345967 0.121656 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4103(3) 0.13781(18) 0.22806(17) 0.0491(4) Uani 1 1 d . . . . .
H3 H 0.326972 0.067688 0.192524 0.059 Uiso 1 1 calc R U . . .
C4 C 0.5964(3) 0.07587(17) 0.32339(17) 0.0462(4) Uani 1 1 d . . . . .
H4 H 0.638027 -0.036488 0.352475 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7217(3) 0.17886(17) 0.37624(16) 0.0425(3) Uani 1 1 d . . . . .
H5 H 0.846878 0.135326 0.440748 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6625(2) 0.34748(15) 0.33386(13) 0.0337(3) Uani 1 1 d . . . . .
C7 C 0.3959(2) 0.59100(16) 0.18896(14) 0.0357(3) Uani 1 1 d . . . . .
C8 C 0.0823(3) 0.80184(19) 0.0775(2) 0.0550(4) Uani 1 1 d . . . . .
H8A H -0.083166 0.817234 0.042272 0.083 Uiso 1 1 calc R U . . .
H8B H 0.193989 0.840825 0.003027 0.083 Uiso 1 1 calc R U . . .
H8C H 0.066524 0.862817 0.161516 0.083 Uiso 1 1 calc R U . . .
C9 C 0.9550(2) 0.42266(16) 0.48832(13) 0.0355(3) 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 C7 1.3322(16) . ?
O1 C8 1.4403(17) . ?
O2 C9 1.2160(16) . ?
O3 C7 1.2070(16) . ?
N1 C9 1.3440(16) . ?
N1 C6 1.4044(16) . ?
N1 H1 0.8600 . ?
C1 C2 1.3935(18) . ?
C1 C6 1.4102(18) . ?
C1 C7 1.4860(18) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3932(18) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C9 1.540(3) 2_766 ?
 
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
C7 O1 C8 116.24(11) . . ?
C9 N1 C6 128.49(11) . . ?
C9 N1 H1 115.8 . . ?
C6 N1 H1 115.8 . . ?
C2 C1 C6 118.76(12) . . ?
C2 C1 C7 119.41(12) . . ?
C6 C1 C7 121.82(11) . . ?
C3 C2 C1 121.35(13) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 119.57(13) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.62(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.60(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 N1 121.86(12) . . ?
C5 C6 C1 119.10(12) . . ?
N1 C6 C1 119.04(11) . . ?
O3 C7 O1 122.60(12) . . ?
O3 C7 C1 125.64(12) . . ?
O1 C7 C1 111.75(11) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N1 127.75(12) . . ?
O2 C9 C9 120.98(14) . 2_766 ?
N1 C9 C9 111.27(13) . 2_766 ?
 
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
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 C1 C2 C3 -179.26(13) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 N1 179.71(12) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C9 N1 C6 C5 -5.8(2) . . . . ?
C9 N1 C6 C1 173.63(12) . . . . ?
C2 C1 C6 C5 -0.05(19) . . . . ?
C7 C1 C6 C5 178.88(12) . . . . ?
C2 C1 C6 N1 -179.53(12) . . . . ?
C7 C1 C6 N1 -0.60(18) . . . . ?
C8 O1 C7 O3 -5.4(2) . . . . ?
C8 O1 C7 C1 174.05(12) . . . . ?
C2 C1 C7 O3 -171.75(14) . . . . ?
C6 C1 C7 O3 9.3(2) . . . . ?
C2 C1 C7 O1 8.82(18) . . . . ?
C6 C1 C7 O1 -170.10(11) . . . . ?
C6 N1 C9 O2 -1.0(2) . . . . ?
C6 N1 C9 C9 179.49(13) . . . 2_766 ?
 
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 
 _geom_hbond_publ_flag
N1 H1 O2  0.86 2.23 2.6618(15) 111.0 2_766 yes
N1 H1 O3  0.86 1.98 2.6838(14) 138.0 . yes
C5 H5 O2  0.93 2.27 2.8904(18) 124.0 . yes
 
_refine_diff_density_max    0.194
_refine_diff_density_min   -0.149
_refine_diff_density_rms    0.032



