 
data_cu_20180710c_0m_a
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C27 H22 N2 O7' 
_chemical_formula_weight          486.46

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            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    11.4226(11)
_cell_length_b                    10.6852(11)
_cell_length_c                    20.1313(18)
_cell_angle_alpha                 90
_cell_angle_beta                  104.995(5)
_cell_angle_gamma                 90
_cell_volume                      2373.4(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     273(2)
_cell_measurement_reflns_used      8347
_cell_measurement_theta_min        4.06
_cell_measurement_theta_max       61.44
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.361          
_exptl_crystal_F_000              1016
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.220
_exptl_crystal_size_mid           0.210
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.828
_shelx_estimated_absorpt_T_min    0.839
_shelx_estimated_absorpt_T_max    0.852
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       273(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\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             36521
_diffrn_reflns_av_unetI/netI      0.0838
_diffrn_reflns_av_R_equivalents   0.1291
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          4.548
_diffrn_reflns_theta_max          80.125
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.968
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.968
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.968
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              5020
_reflns_number_gt                 2313
_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     'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0970P)²] 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          5020
_refine_ls_number_parameters      326
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1548
_refine_ls_R_factor_gt            0.0659
_refine_ls_wR_factor_ref          0.2020
_refine_ls_wR_factor_gt           0.1589
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_restrained_S_all       1.017
_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
C1 C 0.6463(3) 0.6201(3) 0.31877(14) 0.0662(9) Uani 1 1 d . . . . .
C2 C 0.7448(3) 0.6642(4) 0.29965(16) 0.0906(12) Uani 1 1 d . . . . .
H2 H 0.744809 0.671267 0.253598 0.109 Uiso 1 1 calc R U . . .
C3 C 0.8449(3) 0.6981(4) 0.35180(18) 0.0953(12) Uani 1 1 d . . . . .
H3 H 0.913204 0.729846 0.340669 0.114 Uiso 1 1 calc R U . . .
C4 C 0.8448(3) 0.6856(4) 0.41944(16) 0.0851(11) Uani 1 1 d . . . . .
H4 H 0.914098 0.706358 0.453516 0.102 Uiso 1 1 calc R U . . .
C5 C 0.7439(3) 0.6428(3) 0.43794(15) 0.0717(9) Uani 1 1 d . . . . .
H5 H 0.743730 0.635910 0.483965 0.086 Uiso 1 1 calc R U . . .
C6 C 0.6437(3) 0.6105(3) 0.38665(13) 0.0579(8) Uani 1 1 d . . . . .
C7 C 0.5200(3) 0.5603(3) 0.38549(13) 0.0590(8) Uani 1 1 d . . . . .
H7 H 0.522515 0.504430 0.424445 0.071 Uiso 1 1 calc R U . . .
C8 C 0.4217(2) 0.6621(3) 0.37865(12) 0.0509(7) Uani 1 1 d . . . . .
C9 C 0.3145(3) 0.6041(3) 0.39968(15) 0.0613(8) Uani 1 1 d . . . . .
C10 C 0.2424(3) 0.6361(3) 0.28266(13) 0.0555(8) Uani 1 1 d . . . . .
H10 H 0.249601 0.558805 0.257785 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3670(2) 0.7019(3) 0.30311(12) 0.0503(7) Uani 1 1 d . . . . .
H11 H 0.351820 0.792153 0.303079 0.060 Uiso 1 1 calc R U . . .
C12 C 0.4458(3) 0.6774(3) 0.25196(12) 0.0551(7) Uani 1 1 d . . . . .
H12 H 0.492955 0.753611 0.250876 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4613(3) 0.7743(3) 0.42587(14) 0.0607(8) Uani 1 1 d . . . . .
C14 C 0.5629(3) 0.8381(3) 0.53778(14) 0.0781(10) Uani 1 1 d . . . . .
H14A H 0.492983 0.883227 0.544230 0.094 Uiso 1 1 calc R U . . .
H14B H 0.614317 0.896578 0.521603 0.094 Uiso 1 1 calc R U . . .
C15 C 0.6304(3) 0.7815(4) 0.60329(15) 0.0950(12) Uani 1 1 d . . . . .
H15A H 0.577893 0.726432 0.619897 0.142 Uiso 1 1 calc R U . . .
H15B H 0.659360 0.846314 0.636505 0.142 Uiso 1 1 calc R U . . .
H15C H 0.697972 0.734894 0.596142 0.142 Uiso 1 1 calc R U . . .
C16 C 0.1406(3) 0.7130(3) 0.24030(14) 0.0589(8) Uani 1 1 d . . . . .
C17 C 0.1193(3) 0.8338(3) 0.25923(18) 0.0782(10) Uani 1 1 d . . . . .
H17 H 0.165458 0.866622 0.300505 0.094 Uiso 1 1 calc R U . . .
C18 C 0.0296(3) 0.9058(4) 0.2171(2) 0.0961(12) Uani 1 1 d . . . . .
H18 H 0.015746 0.986994 0.229876 0.115 Uiso 1 1 calc R U . . .
C19 C -0.0390(3) 0.8572(4) 0.1561(2) 0.1027(13) Uani 1 1 d . . . . .
H19 H -0.098238 0.906257 0.127351 0.123 Uiso 1 1 calc R U . . .
C20 C -0.0208(3) 0.7382(4) 0.13761(18) 0.0882(11) Uani 1 1 d . . . . .
H20 H -0.068144 0.705693 0.096564 0.106 Uiso 1 1 calc R U . . .
C21 C 0.0674(3) 0.6657(3) 0.17936(15) 0.0680(9) Uani 1 1 d . . . . .
H21 H 0.078283 0.583659 0.166675 0.082 Uiso 1 1 calc R U . . .
C22 C 0.3704(2) 0.6546(3) 0.17913(13) 0.0526(7) Uani 1 1 d . . . . .
C23 C 0.3213(2) 0.7555(3) 0.13820(14) 0.0591(8) Uani 1 1 d . . . . .
H23 H 0.335557 0.836281 0.155688 0.071 Uiso 1 1 calc R U . . .
C24 C 0.2517(3) 0.7380(3) 0.07181(14) 0.0649(8) Uani 1 1 d . . . . .
H24 H 0.220662 0.806095 0.044084 0.078 Uiso 1 1 calc R U . . .
C25 C 0.2292(3) 0.6193(3) 0.04773(14) 0.0673(9) Uani 1 1 d . . . . .
C26 C 0.2745(3) 0.5167(3) 0.08706(15) 0.0751(9) Uani 1 1 d . . . . .
H26 H 0.257038 0.436208 0.069706 0.090 Uiso 1 1 calc R U . . .
C27 C 0.3465(3) 0.5350(3) 0.15272(14) 0.0668(8) Uani 1 1 d . . . . .
H27 H 0.379257 0.466421 0.179545 0.080 Uiso 1 1 calc R U . . .
N1 N 0.5346(2) 0.5733(2) 0.27386(11) 0.0647(7) Uani 1 1 d . . . . .
N2 N 0.1557(3) 0.5995(4) -0.02230(15) 0.0996(11) Uani 1 1 d . . . . .
O1 O 0.48809(18) 0.49392(18) 0.32080(9) 0.0650(6) Uani 1 1 d . . . . .
O2 O 0.4377(3) 0.8793(2) 0.40929(11) 0.0964(8) Uani 1 1 d . . . . .
O3 O 0.52395(18) 0.73823(19) 0.48768(9) 0.0661(6) Uani 1 1 d . . . . .
O4 O 0.3146(2) 0.5614(2) 0.45461(10) 0.0796(7) Uani 1 1 d . . . . .
O5 O 0.21461(19) 0.6043(2) 0.34741(10) 0.0701(6) Uani 1 1 d . . . . .
O6 O 0.1221(3) 0.6886(3) -0.05864(13) 0.1294(12) Uani 1 1 d . . . . .
O7 O 0.1307(4) 0.4949(4) -0.04168(16) 0.203(2) 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
C1 C2 1.364(4) . ?
C1 C6 1.379(4) . ?
C1 N1 1.449(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(4) . ?
C7 O1 1.444(3) . ?
C7 C8 1.544(4) . ?
C7 H7 0.9800 . ?
C8 C13 1.524(4) . ?
C8 C9 1.526(4) . ?
C8 C11 1.547(3) . ?
C9 O4 1.196(3) . ?
C9 O5 1.337(3) . ?
C10 O5 1.459(3) . ?
C10 C16 1.498(4) . ?
C10 C11 1.544(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.556(4) . ?
C11 H11 0.9800 . ?
C12 N1 1.493(4) . ?
C12 C22 1.516(3) . ?
C12 H12 0.9800 . ?
C13 O2 1.182(3) . ?
C13 O3 1.322(3) . ?
C14 O3 1.456(3) . ?
C14 C15 1.474(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.385(4) . ?
C16 C21 1.389(4) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.356(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.383(4) . ?
C22 C23 1.385(4) . ?
C23 C24 1.380(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(4) . ?
C25 N2 1.458(4) . ?
C26 C27 1.378(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
N1 O1 1.468(3) . ?
N2 O7 1.193(4) . ?
N2 O6 1.202(4) . ?
 
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
C2 C1 C6 122.5(3) . . ?
C2 C1 N1 126.9(3) . . ?
C6 C1 N1 110.6(3) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 C7 134.3(3) . . ?
C1 C6 C7 105.8(3) . . ?
O1 C7 C6 101.9(2) . . ?
O1 C7 C8 104.9(2) . . ?
C6 C7 C8 114.1(2) . . ?
O1 C7 H7 111.8 . . ?
C6 C7 H7 111.8 . . ?
C8 C7 H7 111.8 . . ?
C13 C8 C9 106.1(2) . . ?
C13 C8 C7 114.0(2) . . ?
C9 C8 C7 107.8(2) . . ?
C13 C8 C11 112.1(2) . . ?
C9 C8 C11 103.6(2) . . ?
C7 C8 C11 112.4(2) . . ?
O4 C9 O5 121.6(3) . . ?
O4 C9 C8 127.1(3) . . ?
O5 C9 C8 111.3(2) . . ?
O5 C10 C16 108.6(2) . . ?
O5 C10 C11 105.4(2) . . ?
C16 C10 C11 115.4(2) . . ?
O5 C10 H10 109.1 . . ?
C16 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C10 C11 C8 104.3(2) . . ?
C10 C11 C12 113.5(2) . . ?
C8 C11 C12 116.7(2) . . ?
C10 C11 H11 107.3 . . ?
C8 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
N1 C12 C22 109.8(2) . . ?
N1 C12 C11 113.3(2) . . ?
C22 C12 C11 112.7(2) . . ?
N1 C12 H12 106.9 . . ?
C22 C12 H12 106.9 . . ?
C11 C12 H12 106.9 . . ?
O2 C13 O3 124.8(3) . . ?
O2 C13 C8 124.2(3) . . ?
O3 C13 C8 111.1(3) . . ?
O3 C14 C15 108.3(3) . . ?
O3 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O3 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.3(3) . . ?
C17 C16 C10 121.4(3) . . ?
C21 C16 C10 120.3(3) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.9(3) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C27 C22 C23 118.8(3) . . ?
C27 C22 C12 121.8(3) . . ?
C23 C22 C12 119.4(3) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 118.8(3) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 122.1(3) . . ?
C24 C25 N2 119.3(3) . . ?
C26 C25 N2 118.6(3) . . ?
C25 C26 C27 118.8(3) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C26 C27 C22 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C1 N1 O1 101.8(2) . . ?
C1 N1 C12 110.4(2) . . ?
O1 N1 C12 106.78(19) . . ?
O7 N2 O6 122.1(3) . . ?
O7 N2 C25 118.8(4) . . ?
O6 N2 C25 119.1(4) . . ?
C7 O1 N1 104.35(19) . . ?
C13 O3 C14 115.6(2) . . ?
C9 O5 C10 111.4(2) . . ?
 
_refine_diff_density_max    0.195
_refine_diff_density_min   -0.232
_refine_diff_density_rms    0.056



