# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 207/297

data_iwamoto1s3 

 

_audit_creation_method            SHELXL-97 

_chemical_name_systematic 

; 

 ? 

; 

_chemical_name_common             ? 

_chemical_formula_moiety          ? 

_chemical_formula_sum  'C30 H22 Cl2 O4' 

_chemical_formula_weight          517.38 

 

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' 

 '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' 

 

_symmetry_cell_setting            triclinic  

_symmetry_space_group_name_H-M    'P -1'

 

loop_ 

 _symmetry_equiv_pos_as_xyz 

 'x, y, z' 

 '-x, -y, -z' 

 

_cell_length_a                    12.027(3) 

_cell_length_b                    12.291(5) 

_cell_length_c                    8.642(2) 

_cell_angle_alpha                 93.98(3) 

_cell_angle_beta                  95.05(2) 

_cell_angle_gamma                 75.60(3) 

_cell_volume                      1231.1(7) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     293 

_cell_measurement_reflns_used     25

_cell_measurement_theta_min       27.2 

_cell_measurement_theta_max       28.5 

 

_exptl_crystal_description        prismatic 

_exptl_crystal_colour             colorless 

_exptl_crystal_size_max           0.3 

_exptl_crystal_size_mid           0.2 

_exptl_crystal_size_min           0.1 

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.396 

_exptl_crystal_density_method     'not measured' 

_exptl_crystal_F_000              536 

_exptl_absorpt_coefficient_mu     2.666 

_exptl_absorpt_correction_type    none 

_exptl_absorpt_correction_T_min   ? 

_exptl_absorpt_correction_T_max   ? 

 

_exptl_special_details 

; 

 ? 

; 

 

_diffrn_ambient_temperature       293 

_diffrn_radiation_wavelength      1.54180 

_diffrn_radiation_type            CuK\a 

_diffrn_radiation_source          'rotated anode' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device_type   'Rigaku AFC5R'

_diffrn_measurement_method        '\w-2\q' 

_diffrn_detector_area_resol_mean  ? 

_diffrn_standards_number          3 

_diffrn_standards_interval_count  100 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         0.05 

_diffrn_reflns_number             3568 

_diffrn_reflns_av_R_equivalents   0.0161 

_diffrn_reflns_av_sigmaI/netI     0.0342 

_diffrn_reflns_limit_h_min        0 

_diffrn_reflns_limit_h_max        13 

_diffrn_reflns_limit_k_min        -13 

_diffrn_reflns_limit_k_max        13 

_diffrn_reflns_limit_l_min        -9 

_diffrn_reflns_limit_l_max        9 

_diffrn_reflns_theta_min          3.72 

_diffrn_reflns_theta_max          62.03 

_reflns_number_total              2563 

_reflns_number_gt                 2493 

_reflns_threshold_expression      >2sigma(I) 

 

_computing_data_collection        'AFC5R software' 

_computing_cell_refinement        'AFC5R software' 

_computing_data_reduction         'home program' 

_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 

_computing_molecular_graphics     'ORTEP (Johnson, 1976)' 

_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 

 

_refine_special_details 

; 

 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 

 goodness of fit S are based on F^2^, conventional R-factors R are based 

 on F, with F set to zero for negative F^2^. The threshold expression of 

 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F^2^ are statistically about twice as large as those based on F, and R- 

 factors based on ALL data will be even larger. 

; 

 

_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme 

 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+2.0102P] where P=(Fo^2^+2Fc^2^)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     mixed 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          2563 

_refine_ls_number_parameters      327 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.0610 

_refine_ls_R_factor_gt            0.0590 

_refine_ls_wR_factor_ref          0.1403 

_refine_ls_wR_factor_gt           0.1387 

_refine_ls_goodness_of_fit_ref    1.135 

_refine_ls_restrained_S_all       1.135 

_refine_ls_shift/su_max           0.114 

_refine_ls_shift/su_mean          0.020 

 

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_calc_flag 

 _atom_site_refinement_flags 

 _atom_site_disorder_assembly 

 _atom_site_disorder_group 

Cl1 Cl 0.81155(14) 0.25000(12) 0.42048(17) 0.0632(5) Uani 1 d . . . 

Cl2 Cl 0.37209(14) -0.67454(14) 0.7207(2) 0.0748(5) Uani 1 d . . . 

O1 O 1.1100(3) -0.4032(3) 0.8214(4) 0.0521(10) Uani 1 d . . . 

O2 O 0.8486(3) -0.2327(3) 1.2979(4) 0.0551(10) Uani 1 d . . . 

O3 O 0.4962(3) -0.0093(3) 0.7802(5) 0.0597(11) Uani 1 d . . . 

O4 O 0.9076(3) -0.0691(3) 1.0869(4) 0.0497(9) Uani 1 d . . . 

C1 C 1.0754(4) -0.4097(4) 1.0817(6) 0.0392(12) Uani 1 d . . . 

H1 H 1.1456 -0.4616 1.0991 0.047 Uiso 1 calc R . . 

C2 C 1.0419(4) -0.3705(4) 0.9253(6) 0.0370(12) Uani 1 d . . . 

C3 C 0.9212(4) -0.2931(4) 0.8927(5) 0.0318(11) Uani 1 d . . . 

C4 C 0.8876(4) -0.2511(4) 0.7533(6) 0.0342(11) Uani 1 d . . . 

H4 H 0.9401 -0.2727 0.6774 0.041 Uiso 1 calc R . . 

C5 C 0.7707(4) -0.1701(4) 0.7036(5) 0.0333(11) Uani 1 d . . . 

H5 H 0.7353 -0.2109 0.6197 0.040 Uiso 1 calc . . . 

C6 C 0.6835(4) -0.1445(4) 0.8374(5) 0.0330(11) Uani 1 d . . . 

C7 C 0.5972(4) -0.0243(4) 0.8308(6) 0.0382(12) Uani 1 d . . . 

C8 C 0.6389(4) 0.0729(4) 0.8870(6) 0.0394(12) Uani 1 d . . . 

H8 H 0.5950 0.1443 0.8634 0.047 Uiso 1 calc R . . 

C9 C 0.7398(4) 0.0629(4) 0.9728(6) 0.0373(11) Uani 1 d . . . 

C10 C 0.8095(4) -0.0520(4) 1.0249(5) 0.0351(11) Uani 1 d . . . 

C11 C 0.7519(4) -0.1479(4) 1.0012(5) 0.0316(11) Uani 1 d . . . 

H11 H 0.6962 -0.1382 1.0803 0.038 Uiso 1 calc . . . 

C12 C 0.8395(4) -0.2646(4) 1.0228(5) 0.0313(10) Uani 1 d . . . 

H12 H 0.7924 -0.3196 1.0067 0.038 Uiso 1 calc . . . 

C13 C 0.8967(4) -0.2829(4) 1.1846(6) 0.0371(12) Uani 1 d . . . 

C14 C 1.0094(4) -0.3745(4) 1.2029(6) 0.0382(12) Uani 1 d . . . 

C15 C 0.7911(5) 0.1588(4) 1.0129(7) 0.0523(14) Uani 1 d . . . 

H15A H 0.7438 0.2245 0.9652 0.078 Uiso 1 calc R . . 

H15B H 0.8667 0.1424 0.9759 0.078 Uiso 1 calc R . . 

H15C H 0.7962 0.1721 1.1238 0.078 Uiso 1 calc R . . 

C16 C 1.0392(5) -0.4242(5) 1.3601(6) 0.0555(15) Uani 1 d . . . 

H16A H 1.1132 -0.4765 1.3608 0.083 Uiso 1 calc R . . 

H16B H 0.9821 -0.4625 1.3813 0.083 Uiso 1 calc R . . 

H16C H 1.0411 -0.3652 1.4384 0.083 Uiso 1 calc R . . 

C17 C 0.7854(4) -0.0659(4) 0.6325(5) 0.0331(11) Uani 1 d . . . 

C18 C 0.8794(4) -0.0236(4) 0.6741(6) 0.0368(11) Uani 1 d . . . 

H18 H 0.9368 -0.0599 0.7453 0.044 Uiso 1 calc R . . 

C19 C 0.8885(4) 0.0733(4) 0.6098(6) 0.0402(12) Uani 1 d . . . 

H19 H 0.9519 0.1027 0.6385 0.048 Uiso 1 calc R . . 

C20 C 0.8025(5) 0.1274(4) 0.5013(6) 0.0424(12) Uani 1 d . . . 

C21 C 0.7102(5) 0.0850(5) 0.4541(6) 0.0472(13) Uani 1 d . . . 

H21 H 0.6539 0.1209 0.3812 0.057 Uiso 1 calc R . . 

C22 C 0.7025(4) -0.0121(4) 0.5168(6) 0.0414(12) Uani 1 d . . . 

H22 H 0.6414 -0.0436 0.4827 0.050 Uiso 1 calc R . . 

C23 C 0.6158(4) -0.2305(4) 0.8326(6) 0.0380(12) Uani 1 d . . . 

H23 H 0.5524 -0.2138 0.8922 0.046 Uiso 1 calc R . . 

C24 C 0.6358(4) -0.3288(4) 0.7526(6) 0.0426(12) Uani 1 d . . . 

H24 H 0.6982 -0.3449 0.6913 0.051 Uiso 1 calc R . . 

C25 C 0.5707(4) -0.4135(4) 0.7507(6) 0.0405(12) Uani 1 d . . . 

C26 C 0.6136(5) -0.5193(4) 0.6747(7) 0.0568(16) Uani 1 d . . . 

H26 H 0.6831 -0.5337 0.6285 0.068 Uiso 1 calc R . . 

C27 C 0.5536(5) -0.6003(5) 0.6687(8) 0.0639(17) Uani 1 d . . . 

H27 H 0.5816 -0.6707 0.6206 0.077 Uiso 1 calc R . . 

C28 C 0.4502(4) -0.5744(4) 0.7362(7) 0.0476(14) Uani 1 d . . . 

C29 C 0.4063(5) -0.4717(5) 0.8115(8) 0.0590(16) Uani 1 d . . . 

H29 H 0.3367 -0.4581 0.8573 0.071 Uiso 1 calc R . . 

C30 C 0.4655(5) -0.3910(5) 0.8179(7) 0.0569(16) Uani 1 d . . . 

H30 H 0.4364 -0.3211 0.8667 0.068 Uiso 1 calc R . . 

 

loop_ 

 _atom_site_aniso_label 

 _atom_site_aniso_U_11 

 _atom_site_aniso_U_22 

 _atom_site_aniso_U_33 

 _atom_site_aniso_U_23 

 _atom_site_aniso_U_13 

 _atom_site_aniso_U_12 

Cl1 0.0873(11) 0.0555(9) 0.0570(9) 0.0101(7) 0.0048(8) -0.0348(8) 

Cl2 0.0699(10) 0.0663(10) 0.1038(13) 0.0061(9) 0.0107(9) -0.0443(8) 

O1 0.039(2) 0.058(2) 0.060(2) 0.0056(19) 0.0191(18) -0.0054(18) 

O2 0.059(2) 0.067(3) 0.036(2) -0.0052(19) 0.0083(18) -0.009(2) 

O3 0.032(2) 0.062(2) 0.082(3) 0.006(2) -0.0127(19) -0.0101(18) 

O4 0.035(2) 0.060(2) 0.056(2) -0.0037(18) -0.0068(17) -0.0199(17) 

C1 0.031(3) 0.031(3) 0.054(3) 0.006(2) -0.002(2) -0.006(2) 

C2 0.030(3) 0.033(3) 0.052(3) -0.001(2) 0.010(2) -0.014(2) 

C3 0.029(2) 0.033(3) 0.037(3) -0.002(2) 0.008(2) -0.012(2) 

C4 0.029(3) 0.035(3) 0.040(3) -0.003(2) 0.010(2) -0.009(2) 

C5 0.028(2) 0.041(3) 0.033(3) -0.002(2) 0.005(2) -0.012(2) 

C6 0.027(2) 0.041(3) 0.034(3) -0.001(2) 0.003(2) -0.013(2) 

C7 0.028(3) 0.047(3) 0.040(3) 0.001(2) 0.002(2) -0.012(2) 

C8 0.035(3) 0.034(3) 0.048(3) -0.002(2) 0.009(2) -0.005(2) 

C9 0.036(3) 0.037(3) 0.040(3) -0.008(2) 0.010(2) -0.012(2) 

C10 0.029(3) 0.041(3) 0.035(3) -0.009(2) 0.007(2) -0.011(2) 

C11 0.024(2) 0.040(3) 0.032(3) -0.002(2) 0.0055(19) -0.012(2) 

C12 0.026(2) 0.035(3) 0.035(3) -0.001(2) 0.008(2) -0.010(2) 

C13 0.036(3) 0.039(3) 0.041(3) 0.000(2) 0.005(2) -0.016(2) 

C14 0.036(3) 0.036(3) 0.044(3) 0.000(2) -0.003(2) -0.015(2) 

C15 0.057(3) 0.044(3) 0.058(4) -0.015(3) 0.011(3) -0.020(3) 

C16 0.063(4) 0.065(4) 0.039(3) 0.010(3) -0.010(3) -0.020(3) 

C17 0.031(3) 0.036(3) 0.032(3) -0.002(2) 0.000(2) -0.010(2) 

C18 0.027(3) 0.046(3) 0.039(3) -0.002(2) 0.002(2) -0.012(2) 

C19 0.038(3) 0.053(3) 0.035(3) 0.001(2) 0.004(2) -0.021(2) 

C20 0.055(3) 0.041(3) 0.037(3) -0.004(2) 0.011(2) -0.023(3) 

C21 0.055(3) 0.055(3) 0.033(3) 0.003(2) -0.006(2) -0.019(3) 

C22 0.044(3) 0.046(3) 0.039(3) -0.001(2) -0.003(2) -0.023(2) 

C23 0.027(2) 0.048(3) 0.043(3) -0.006(2) 0.004(2) -0.018(2) 

C24 0.029(3) 0.045(3) 0.058(3) -0.002(3) 0.008(2) -0.016(2) 

C25 0.026(3) 0.045(3) 0.053(3) 0.003(2) 0.001(2) -0.015(2) 

C26 0.047(3) 0.050(3) 0.080(4) -0.015(3) 0.024(3) -0.023(3) 

C27 0.056(4) 0.050(3) 0.092(5) -0.018(3) 0.020(3) -0.025(3) 

C28 0.037(3) 0.045(3) 0.068(4) 0.010(3) 0.000(3) -0.023(3) 

C29 0.037(3) 0.053(4) 0.094(5) 0.002(3) 0.022(3) -0.018(3) 

C30 0.043(3) 0.047(3) 0.087(4) -0.012(3) 0.024(3) -0.022(3) 

 

_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 C20 1.736(5) . ? 

Cl2 C28 1.716(5) . ? 

O1 C2 1.247(6) . ? 

O2 C13 1.230(6) . ? 

O3 C7 1.228(5) . ? 

O4 C10 1.226(5) . ? 

C1 C14 1.352(7) . ? 

C1 C2 1.456(7) . ? 

C2 C3 1.539(7) . ? 

C3 C4 1.334(7) . ? 

C3 C12 1.524(6) . ? 

C4 C5 1.552(6) . ? 

C5 C17 1.513(6) . ? 

C5 C6 1.592(6) . ? 

C6 C23 1.482(6) . ? 

C6 C11 1.571(6) . ? 

C6 C7 1.581(7) . ? 

C7 C8 1.446(6) . ? 

C8 C9 1.348(7) . ? 

C9 C15 1.468(7) . ? 

C9 C10 1.527(7) . ? 

C10 C11 1.503(6) . ? 

C11 C12 1.566(6) . ? 

C12 C13 1.509(7) . ? 

C13 C14 1.535(7) . ? 

C14 C16 1.506(7) . ? 

C17 C18 1.369(6) . ? 

C17 C22 1.421(7) . ? 

C18 C19 1.381(7) . ? 

C19 C20 1.401(7) . ? 

C20 C21 1.360(7) . ? 

C21 C22 1.371(7) . ? 

C23 C24 1.329(7) . ? 

C24 C25 1.449(6) . ? 

C25 C30 1.395(7) . ? 

C25 C26 1.412(7) . ? 

C26 C27 1.363(7) . ? 

C27 C28 1.376(8) . ? 

C28 C29 1.383(8) . ? 

C29 C30 1.353(7) . ? 

 

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 

C14 C1 C2 123.1(5) . . ? 

O1 C2 C1 119.2(5) . . ? 

O1 C2 C3 122.3(5) . . ? 

C1 C2 C3 118.5(4) . . ? 

C4 C3 C12 119.9(4) . . ? 

C4 C3 C2 121.1(4) . . ? 

C12 C3 C2 119.0(4) . . ? 

C3 C4 C5 127.2(4) . . ? 

C17 C5 C4 112.5(4) . . ? 

C17 C5 C6 113.9(4) . . ? 

C4 C5 C6 112.7(4) . . ? 

C23 C6 C11 107.1(4) . . ? 

C23 C6 C7 108.6(4) . . ? 

C11 C6 C7 106.2(4) . . ? 

C23 C6 C5 111.1(4) . . ? 

C11 C6 C5 110.0(3) . . ? 

C7 C6 C5 113.5(4) . . ? 

O3 C7 C8 118.1(5) . . ? 

O3 C7 C6 123.2(4) . . ? 

C8 C7 C6 118.6(4) . . ? 

C9 C8 C7 121.7(5) . . ? 

C8 C9 C15 122.4(5) . . ? 

C8 C9 C10 120.6(4) . . ? 

C15 C9 C10 116.9(4) . . ? 

O4 C10 C11 119.0(4) . . ? 

O4 C10 C9 123.8(4) . . ? 

C11 C10 C9 117.2(4) . . ? 

C10 C11 C12 112.1(4) . . ? 

C10 C11 C6 110.5(4) . . ? 

C12 C11 C6 111.0(4) . . ? 

C13 C12 C3 114.9(4) . . ? 

C13 C12 C11 115.2(4) . . ? 

C3 C12 C11 111.3(4) . . ? 

O2 C13 C12 120.3(4) . . ? 

O2 C13 C14 121.7(4) . . ? 

C12 C13 C14 117.6(4) . . ? 

C1 C14 C16 122.6(5) . . ? 

C1 C14 C13 121.0(4) . . ? 

C16 C14 C13 116.4(5) . . ? 

C18 C17 C22 118.7(4) . . ? 

C18 C17 C5 121.2(4) . . ? 

C22 C17 C5 120.0(4) . . ? 

C17 C18 C19 119.6(5) . . ? 

C18 C19 C20 120.2(4) . . ? 

C21 C20 C19 121.3(5) . . ? 

C21 C20 Cl1 117.7(4) . . ? 

C19 C20 Cl1 120.9(4) . . ? 

C20 C21 C22 118.2(5) . . ? 

C21 C22 C17 121.8(4) . . ? 

C24 C23 C6 127.1(4) . . ? 

C23 C24 C25 126.9(5) . . ? 

C30 C25 C26 120.0(4) . . ? 

C30 C25 C24 121.1(5) . . ? 

C26 C25 C24 118.8(4) . . ? 

C27 C26 C25 120.3(5) . . ? 

C26 C27 C28 117.8(5) . . ? 

C27 C28 C29 123.0(5) . . ? 

C27 C28 Cl2 117.5(4) . . ? 

C29 C28 Cl2 119.4(4) . . ? 

C30 C29 C28 119.4(5) . . ? 

C29 C30 C25 119.4(5) . . ? 

 

_diffrn_measured_fraction_theta_max    0.664 

_diffrn_reflns_theta_full              62.03 

_diffrn_measured_fraction_theta_full   0.664 

_refine_diff_density_max    0.214 

_refine_diff_density_min   -0.310 

_refine_diff_density_rms    0.058