 
data_cu_20180131a_0m_a
 
_audit_creation_method            'SHELXL-2018/1'
_shelx_SHELXL_version_number      '2018/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C33 H26 Cl N O5' 
_chemical_formula_weight          552.00

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'
 'Cl'  'Cl'   0.3639   0.7018
 '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                    11.3905(2)
_cell_length_b                    6.8267(2)
_cell_length_c                    18.0192(4)
_cell_angle_alpha                 90
_cell_angle_beta                  102.2960(10)
_cell_angle_gamma                 90
_cell_volume                      1369.02(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     273(2)
_cell_measurement_reflns_used      9950
_cell_measurement_theta_min        2.51
_cell_measurement_theta_max       67.89
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.339          
_exptl_crystal_F_000              576
_exptl_transmission_factor_min    0.1808	
_exptl_transmission_factor_max    0.7531
_exptl_crystal_size_max           0.210
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.190
_exptl_absorpt_coefficient_mu     1.595
_shelx_estimated_absorpt_T_min    0.731
_shelx_estimated_absorpt_T_max    0.751
_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             36346
_diffrn_reflns_av_unetI/netI      0.0372
_diffrn_reflns_av_R_equivalents   0.0680
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.510
_diffrn_reflns_theta_max          68.181
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.990
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.990
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              4950
_reflns_number_gt                 4213
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.828
_reflns_Friedel_fraction_max      0.983
_reflns_Friedel_fraction_full     0.996
 
_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-2018/1 (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)+(0.0160P)²+0.3834P] 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_abs_structure_details
;
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.181(8)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          4950
_refine_ls_number_parameters      362
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0496
_refine_ls_R_factor_gt            0.0371
_refine_ls_wR_factor_ref          0.0760
_refine_ls_wR_factor_gt           0.0708
_refine_ls_goodness_of_fit_ref    1.099
_refine_ls_restrained_S_all       1.099
_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
Cl1 Cl 0.38722(7) 0.69363(14) 0.58652(4) 0.0459(2) Uani 1 1 d . . . . .
O3 O 0.38346(19) 0.3920(3) 0.22748(12) 0.0399(6) Uani 1 1 d . . . . .
O5 O 0.04599(19) 0.6016(4) 0.24712(14) 0.0531(7) Uani 1 1 d . . . . .
O1 O 0.76950(18) 0.7465(5) 0.38008(12) 0.0559(8) Uani 1 1 d . . . . .
O2 O 0.3228(3) 0.1264(4) 0.28060(16) 0.0581(7) Uani 1 1 d . . . . .
O4 O 0.0726(2) 0.3108(4) 0.19487(15) 0.0601(7) Uani 1 1 d . . . . .
N1 N 0.5546(2) 0.6804(5) 0.29901(12) 0.0391(7) Uani 1 1 d . . . . .
H1 H 0.629091 0.658446 0.299564 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3943(2) 0.6615(5) 0.36584(15) 0.0296(7) Uani 1 1 d . . . . .
C14 C 0.3002(3) 0.6378(5) 0.29251(16) 0.0314(7) Uani 1 1 d . . . . .
H14 H 0.245507 0.750236 0.284219 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5177(2) 0.6813(5) 0.36577(15) 0.0312(7) Uani 1 1 d . . . . .
C9 C 0.5597(2) 0.6998(6) 0.50374(15) 0.0333(6) Uani 1 1 d . . . . .
H9 H 0.614101 0.711879 0.549993 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3575(3) 0.6630(5) 0.43400(16) 0.0330(7) Uani 1 1 d . . . . .
H11 H 0.276240 0.649263 0.433894 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4388(3) 0.6843(5) 0.50259(15) 0.0326(7) Uani 1 1 d . . . . .
C18 C 0.1073(3) 0.4411(6) 0.23826(19) 0.0440(9) Uani 1 1 d . . . . .
C1 C 0.8235(3) 0.7252(5) 0.51131(16) 0.0355(8) Uani 1 1 d . . . . .
C8 C 0.6019(2) 0.6975(6) 0.43643(15) 0.0319(6) Uani 1 1 d . . . . .
C7 C 0.7315(3) 0.7242(5) 0.43813(16) 0.0364(8) Uani 1 1 d . . . . .
C15 C 0.3554(3) 0.6018(5) 0.22247(17) 0.0334(7) Uani 1 1 d . . . . .
C22 C 0.2688(3) 0.6469(5) 0.14722(16) 0.0372(8) Uani 1 1 d . . . . .
C17 C 0.2303(3) 0.4454(5) 0.29269(18) 0.0361(8) Uani 1 1 d . . . . .
H17 H 0.221455 0.415215 0.344393 0.043 Uiso 1 1 calc R U . . .
C21 C 0.3130(3) 0.2997(6) 0.2680(2) 0.0419(9) Uani 1 1 d . . . . .
C23 C 0.2474(3) 0.5109(6) 0.08873(19) 0.0495(10) Uani 1 1 d . . . . .
H23 H 0.283376 0.387998 0.095572 0.059 Uiso 1 1 calc R U . . .
C16 C 0.4731(2) 0.7153(6) 0.22690(15) 0.0359(7) Uani 1 1 d . . . . .
H16 H 0.453308 0.855129 0.224352 0.043 Uiso 1 1 calc R U . . .
C28 C 0.5356(3) 0.6713(7) 0.16294(16) 0.0441(9) Uani 1 1 d . . . . .
C2 C 0.8312(3) 0.5745(6) 0.56367(19) 0.0461(9) Uani 1 1 d . . . . .
H2 H 0.771642 0.479005 0.557236 0.055 Uiso 1 1 calc R U . . .
C6 C 0.9103(3) 0.8692(6) 0.52277(19) 0.0463(9) Uani 1 1 d . . . . .
H6 H 0.905933 0.971339 0.488125 0.056 Uiso 1 1 calc R U . . .
C3 C 0.9272(3) 0.5649(6) 0.6257(2) 0.0561(11) Uani 1 1 d . . . . .
H3 H 0.933743 0.461176 0.659758 0.067 Uiso 1 1 calc R U . . .
C29 C 0.5946(3) 0.4953(7) 0.1594(2) 0.0577(11) Uani 1 1 d . . . . .
H29 H 0.596797 0.401618 0.197152 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0044(3) 0.8618(7) 0.5860(2) 0.0576(11) Uani 1 1 d . . . . .
H5 H 1.062000 0.960527 0.594232 0.069 Uiso 1 1 calc R U . . .
C27 C 0.2139(3) 0.8282(6) 0.1359(2) 0.0475(9) Uani 1 1 d . . . . .
H27 H 0.227755 0.920245 0.174854 0.057 Uiso 1 1 calc R U . . .
C25 C 0.1175(3) 0.7382(8) 0.0091(2) 0.0660(14) Uani 1 1 d . . . . .
H25 H 0.066571 0.768657 -0.037076 0.079 Uiso 1 1 calc R U . . .
C26 C 0.1385(3) 0.8742(7) 0.0673(2) 0.0605(11) Uani 1 1 d . . . . .
H26 H 0.101904 0.996545 0.060346 0.073 Uiso 1 1 calc R U . . .
C24 C 0.1719(4) 0.5590(8) 0.0197(2) 0.0639(13) Uani 1 1 d . . . . .
H24 H 0.158351 0.468108 -0.019670 0.077 Uiso 1 1 calc R U . . .
C4 C 1.0125(3) 0.7102(8) 0.63617(18) 0.0570(11) Uani 1 1 d . . . . .
H4 H 1.076440 0.705244 0.677932 0.068 Uiso 1 1 calc R U . . .
C33 C 0.5337(3) 0.8096(8) 0.1067(2) 0.0654(13) Uani 1 1 d . . . . .
H33 H 0.494421 0.928276 0.108804 0.078 Uiso 1 1 calc R U . . .
C31 C 0.6472(4) 0.5980(11) 0.0433(3) 0.093(2) Uani 1 1 d . . . . .
H31 H 0.684068 0.572854 0.002972 0.112 Uiso 1 1 calc R U . . .
C20 C -0.1186(4) 0.8164(8) 0.2065(3) 0.0837(16) Uani 1 1 d . . . . .
H20A H -0.120847 0.834198 0.259022 0.126 Uiso 1 1 calc R U . . .
H20B H -0.198202 0.830279 0.175916 0.126 Uiso 1 1 calc R U . . .
H20C H -0.066864 0.913130 0.191703 0.126 Uiso 1 1 calc R U . . .
C30 C 0.6504(4) 0.4591(9) 0.0994(3) 0.0806(17) Uani 1 1 d . . . . .
H30 H 0.690080 0.340946 0.097008 0.097 Uiso 1 1 calc R U . . .
C19 C -0.0724(3) 0.6191(7) 0.1955(3) 0.0738(14) Uani 1 1 d . . . . .
H19A H -0.126712 0.519852 0.207167 0.089 Uiso 1 1 calc R U . . .
H19B H -0.065063 0.602123 0.143233 0.089 Uiso 1 1 calc R U . . .
C32 C 0.5898(4) 0.7725(11) 0.0471(2) 0.093(2) Uani 1 1 d . . . . .
H32 H 0.588513 0.866538 0.009557 0.112 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
Cl1 C10 1.737(3) . ?
O3 C21 1.351(4) . ?
O3 C15 1.466(4) . ?
O5 C18 1.327(4) . ?
O5 C19 1.471(4) . ?
O1 C7 1.224(4) . ?
O2 C21 1.205(4) . ?
O4 C18 1.195(4) . ?
N1 C13 1.356(3) . ?
N1 C16 1.446(3) . ?
N1 H1 0.8600 . ?
C12 C11 1.380(4) . ?
C12 C13 1.412(4) . ?
C12 C14 1.522(4) . ?
C14 C17 1.537(5) . ?
C14 C15 1.545(4) . ?
C14 H14 0.9800 . ?
C13 C8 1.426(3) . ?
C9 C10 1.377(4) . ?
C9 C8 1.396(4) . ?
C9 H9 0.9300 . ?
C11 C10 1.385(4) . ?
C11 H11 0.9300 . ?
C18 C17 1.530(4) . ?
C1 C6 1.379(5) . ?
C1 C2 1.386(5) . ?
C1 C7 1.499(4) . ?
C8 C7 1.481(4) . ?
C15 C22 1.529(4) . ?
C15 C16 1.535(4) . ?
C22 C27 1.383(5) . ?
C22 C23 1.387(5) . ?
C17 C21 1.501(5) . ?
C17 H17 0.9800 . ?
C23 C24 1.393(5) . ?
C23 H23 0.9300 . ?
C16 C28 1.508(4) . ?
C16 H16 0.9800 . ?
C28 C33 1.383(5) . ?
C28 C29 1.384(6) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9300 . ?
C6 C5 1.389(5) . ?
C6 H6 0.9300 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C29 C30 1.388(6) . ?
C29 H29 0.9300 . ?
C5 C4 1.364(6) . ?
C5 H5 0.9300 . ?
C27 C26 1.382(5) . ?
C27 H27 0.9300 . ?
C25 C24 1.367(7) . ?
C25 C26 1.383(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C24 H24 0.9300 . ?
C4 H4 0.9300 . ?
C33 C32 1.385(6) . ?
C33 H33 0.9300 . ?
C31 C32 1.368(8) . ?
C31 C30 1.381(8) . ?
C31 H31 0.9300 . ?
C20 C19 1.475(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C30 H30 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C32 H32 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 O3 C15 110.0(3) . . ?
C18 O5 C19 115.2(3) . . ?
C13 N1 C16 122.4(2) . . ?
C13 N1 H1 118.8 . . ?
C16 N1 H1 118.8 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 C14 118.8(2) . . ?
C13 C12 C14 121.8(2) . . ?
C12 C14 C17 111.0(3) . . ?
C12 C14 C15 113.1(2) . . ?
C17 C14 C15 99.6(2) . . ?
C12 C14 H14 110.9 . . ?
C17 C14 H14 110.9 . . ?
C15 C14 H14 110.9 . . ?
N1 C13 C12 119.8(2) . . ?
N1 C13 C8 121.1(2) . . ?
C12 C13 C8 119.1(2) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 Cl1 120.5(2) . . ?
C11 C10 Cl1 119.6(2) . . ?
O4 C18 O5 125.8(3) . . ?
O4 C18 C17 124.3(4) . . ?
O5 C18 C17 109.9(3) . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 C7 118.7(3) . . ?
C2 C1 C7 121.8(3) . . ?
C9 C8 C13 119.1(2) . . ?
C9 C8 C7 120.4(2) . . ?
C13 C8 C7 120.4(2) . . ?
O1 C7 C8 122.0(3) . . ?
O1 C7 C1 116.3(3) . . ?
C8 C7 C1 121.7(3) . . ?
O3 C15 C22 110.0(3) . . ?
O3 C15 C16 108.3(2) . . ?
C22 C15 C16 109.6(3) . . ?
O3 C15 C14 103.1(2) . . ?
C22 C15 C14 113.2(2) . . ?
C16 C15 C14 112.3(2) . . ?
C27 C22 C23 119.1(3) . . ?
C27 C22 C15 119.8(3) . . ?
C23 C22 C15 121.0(3) . . ?
C21 C17 C18 110.1(3) . . ?
C21 C17 C14 102.0(3) . . ?
C18 C17 C14 114.8(3) . . ?
C21 C17 H17 109.9 . . ?
C18 C17 H17 109.9 . . ?
C14 C17 H17 109.9 . . ?
O2 C21 O3 121.2(4) . . ?
O2 C21 C17 129.3(4) . . ?
O3 C21 C17 109.5(3) . . ?
C22 C23 C24 119.7(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
N1 C16 C28 109.7(2) . . ?
N1 C16 C15 110.5(3) . . ?
C28 C16 C15 114.1(3) . . ?
N1 C16 H16 107.4 . . ?
C28 C16 H16 107.4 . . ?
C15 C16 H16 107.4 . . ?
C33 C28 C29 119.4(4) . . ?
C33 C28 C16 119.2(4) . . ?
C29 C28 C16 121.4(4) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C1 C6 C5 120.0(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C28 C29 C30 119.8(5) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C26 C27 C22 120.7(4) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C24 C25 C26 119.6(4) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 120.0(4) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C28 C33 C32 120.4(5) . . ?
C28 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C32 C31 C30 120.0(4) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C31 C30 C29 120.2(5) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
O5 C19 C20 107.1(3) . . ?
O5 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
O5 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.5 . . ?
C31 C32 C33 120.1(5) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
 
_refine_diff_density_max    0.144
_refine_diff_density_min   -0.240
_refine_diff_density_rms    0.040



