 
data_ic20014 
  
_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 
 'C30 H27 I N2 O' 
_chemical_formula_weight          558.43 
  
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' 
 'I'  'I'  -0.3257   6.8362 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            60 
_space_group_name_H-M_alt         'P b c n' 
_space_group_name_Hall            '-P 2n 2ab' 
  
_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+1/2, -y+1/2, z+1/2' 
 '-x, y, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y-1/2, -z-1/2' 
 'x, -y, z-1/2' 
 '-x-1/2, y-1/2, z' 
  
_cell_length_a                    30.4682(9) 
_cell_length_b                    10.0646(3) 
_cell_length_c                    16.1931(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      4965.6(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     19786 
_cell_measurement_theta_min       2.73 
_cell_measurement_theta_max       75.06 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             red 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.494 
_exptl_crystal_F_000              2256 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.180 
_exptl_crystal_size_mid           0.169 
_exptl_crystal_size_min           0.156 
_exptl_absorpt_coefficient_mu     10.321 
_shelx_estimated_absorpt_T_min    0.258 
_shelx_estimated_absorpt_T_max    0.296 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6017 
_exptl_absorpt_correction_T_max   0.7539 
_exptl_absorpt_process_details    'Bruker SADABS' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker D8 VENTURE' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             24717 
_diffrn_reflns_av_unetI/netI      0.0331 
_diffrn_reflns_av_R_equivalents   0.0405 
_diffrn_reflns_limit_h_min        -38 
_diffrn_reflns_limit_h_max        38 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          2.901 
_diffrn_reflns_theta_max          74.995 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.997 
_diffrn_measured_fraction_theta_full  0.998 
_diffrn_reflns_Laue_measured_fraction_max    0.997 
_diffrn_reflns_Laue_measured_fraction_full   0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.997 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
_reflns_number_total              5106 
_reflns_number_gt                 4659 
_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 APEX3' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXT (Sheldrick, 2015)' 
_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)+(0.0986P)²+15.0987P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          5106 
_refine_ls_number_parameters      321 
_refine_ls_number_restraints      7 
_refine_ls_R_factor_all           0.0615 
_refine_ls_R_factor_gt            0.0574 
_refine_ls_wR_factor_ref          0.1711 
_refine_ls_wR_factor_gt           0.1646 
_refine_ls_goodness_of_fit_ref    1.046 
_refine_ls_restrained_S_all       1.046 
_refine_ls_shift/su_max           0.001 
_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 
N1 N 0.43225(11) 0.5762(4) 0.03372(19) 0.0327(8) Uani 1 1 d . . . . . 
N2 N 0.75500(10) 0.8377(3) 0.51278(17) 0.0216(6) Uani 1 1 d . . . . . 
C1 C 0.44705(15) 0.7026(5) 0.0370(3) 0.0366(10) Uani 1 1 d . . . . . 
H1 H 0.431945 0.770466 0.007767 0.044 Uiso 1 1 calc R U . . . 
C2 C 0.48378(14) 0.7341(5) 0.0824(2) 0.0340(9) Uani 1 1 d . . . . . 
H2 H 0.493973 0.823264 0.083871 0.041 Uiso 1 1 calc R U . . . 
C3 C 0.50621(12) 0.6357(4) 0.1264(2) 0.0269(8) Uani 1 1 d . . . . . 
C4 C 0.49040(13) 0.5047(5) 0.1196(2) 0.0339(9) Uani 1 1 d . . . . . 
H4 H 0.505157 0.434131 0.146928 0.041 Uiso 1 1 calc R U . . . 
C5 C 0.45334(14) 0.4794(5) 0.0731(2) 0.0352(9) Uani 1 1 d . . . . . 
H5 H 0.442684 0.390888 0.069216 0.042 Uiso 1 1 calc DR U . . . 
C6 C 0.54479(13) 0.6665(4) 0.1795(2) 0.0252(8) Uani 1 1 d . . . . . 
C7 C 0.57206(13) 0.5659(4) 0.2074(2) 0.0287(8) Uani 1 1 d . . . . . 
H7 H 0.566623 0.476749 0.191057 0.034 Uiso 1 1 calc R U . . . 
C8 C 0.60735(12) 0.5939(4) 0.2593(2) 0.0260(7) Uani 1 1 d . . . . . 
H8 H 0.625896 0.523652 0.277142 0.031 Uiso 1 1 calc R U . . . 
C9 C 0.61597(11) 0.7246(4) 0.2858(2) 0.0198(6) Uani 1 1 d . . . . . 
C10 C 0.58843(13) 0.8249(4) 0.2566(2) 0.0238(7) Uani 1 1 d . . . . . 
H10 H 0.593734 0.914243 0.272793 0.029 Uiso 1 1 calc R U . . . 
C11 C 0.55335(12) 0.7970(4) 0.2044(2) 0.0247(7) Uani 1 1 d . . . . . 
H11 H 0.535070 0.867201 0.185504 0.030 Uiso 1 1 calc R U . . . 
C12 C 0.65222(11) 0.7532(3) 0.3441(2) 0.0187(6) Uani 1 1 d . . . . . 
C13 C 0.65172(11) 0.8677(3) 0.3932(2) 0.0207(6) Uani 1 1 d . . . . . 
H13 H 0.627701 0.927426 0.388766 0.025 Uiso 1 1 calc R U . . . 
C14 C 0.68537(12) 0.8961(3) 0.4481(2) 0.0212(7) Uani 1 1 d . . . . . 
H14 H 0.684437 0.975780 0.479515 0.025 Uiso 1 1 calc R U . . . 
C15 C 0.72062(11) 0.8087(3) 0.45757(19) 0.0178(6) Uani 1 1 d . . . . . 
C16 C 0.72123(12) 0.6922(3) 0.4096(2) 0.0207(7) Uani 1 1 d . . . . . 
H16 H 0.744585 0.630414 0.415664 0.025 Uiso 1 1 calc R U . . . 
C17 C 0.68783(12) 0.6673(4) 0.3536(2) 0.0215(7) Uani 1 1 d . . . . . 
H17 H 0.689231 0.589343 0.320664 0.026 Uiso 1 1 calc R U . . . 
C18 C 0.79798(11) 0.7859(3) 0.4990(2) 0.0185(6) Uani 1 1 d . . . . . 
C19 C 0.81677(12) 0.7927(4) 0.4205(2) 0.0245(7) Uani 1 1 d . . . . . 
H19 H 0.801169 0.832833 0.376232 0.029 Uiso 1 1 calc R U . . . 
C20 C 0.85855(13) 0.7402(4) 0.4074(3) 0.0324(9) Uani 1 1 d . . . . . 
H20 H 0.871205 0.743797 0.353822 0.039 Uiso 1 1 calc R U . . . 
C21 C 0.88166(13) 0.6834(4) 0.4713(3) 0.0347(10) Uani 1 1 d . . . . . 
H21 H 0.910253 0.648851 0.462026 0.042 Uiso 1 1 calc R U . . . 
C22 C 0.86297(13) 0.6766(4) 0.5497(3) 0.0293(8) Uani 1 1 d . . . . . 
H22 H 0.878751 0.636841 0.593874 0.035 Uiso 1 1 calc R U . . . 
C23 C 0.82111(12) 0.7281(4) 0.5634(2) 0.0229(7) Uani 1 1 d . . . . . 
H23 H 0.808420 0.723536 0.616885 0.027 Uiso 1 1 calc R U . . . 
C24 C 0.74723(11) 0.9101(3) 0.58717(19) 0.0194(6) Uani 1 1 d . . . . . 
C25 C 0.70901(12) 0.8902(4) 0.6331(2) 0.0228(7) Uani 1 1 d . . . . . 
H25 H 0.687156 0.830328 0.613962 0.027 Uiso 1 1 calc R U . . . 
C26 C 0.70305(13) 0.9587(4) 0.7072(2) 0.0287(8) Uani 1 1 d . . . . . 
H26 H 0.677010 0.945149 0.738380 0.034 Uiso 1 1 calc R U . . . 
C27 C 0.73456(14) 1.0457(4) 0.7358(2) 0.0293(8) Uani 1 1 d . . . . . 
H27 H 0.730504 1.090801 0.786780 0.035 Uiso 1 1 calc R U . . . 
C28 C 0.77238(14) 1.0671(4) 0.6893(2) 0.0272(8) Uani 1 1 d . . . . . 
H28 H 0.794111 1.127335 0.708428 0.033 Uiso 1 1 calc R U . . . 
C29 C 0.77842(12) 1.0007(4) 0.6151(2) 0.0237(7) Uani 1 1 d . . . . . 
H29 H 0.803994 1.017073 0.583096 0.028 Uiso 1 1 calc R U . . . 
C35 C 0.39081(13) 0.5483(6) -0.0114(3) 0.0411(11) Uani 1 1 d . . . . . 
H35A H 0.391229 0.456684 -0.031917 0.062 Uiso 1 1 calc R U . . . 
H35B H 0.388026 0.609728 -0.058039 0.062 Uiso 1 1 calc R U . . . 
H35C H 0.365828 0.560015 0.026031 0.062 Uiso 1 1 calc R U . . . 
I1 I 0.58165(2) 0.18802(3) 0.18092(2) 0.04987(17) Uani 1 1 d . . . . . 
O1 O 0.4757(3) 0.0892(15) 0.1266(6) 0.090(3) Uani 0.705(17) 1 d D . P A 1 
H1A H 0.496(3) 0.140(10) 0.115(8) 0.136 Uiso 0.705(17) 1 d D U P A 1 
O1' O 0.4700(8) 0.183(4) 0.1363(14) 0.090(3) Uani 0.295(17) 1 d D . P A 2 
H1'A H 0.468(3) 0.253(3) 0.163(2) 0.136 Uiso 0.295(17) 1 d D U P A 2 
H1B H 0.462(3) 0.120(4) 0.166(4) 0.136 Uiso 1 1 d D 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 
N1 C5 1.330(6) . ? 
N1 C1 1.352(6) . ? 
N1 C35 1.486(5) . ? 
N2 C15 1.407(4) . ? 
N2 C18 1.427(4) . ? 
N2 C24 1.428(4) . ? 
C1 C2 1.376(6) . ? 
C2 C3 1.398(6) . ? 
C3 C4 1.408(6) . ? 
C3 C6 1.488(5) . ? 
C4 C5 1.381(6) . ? 
C6 C7 1.386(6) . ? 
C6 C11 1.399(5) . ? 
C7 C8 1.393(5) . ? 
C8 C9 1.408(5) . ? 
C9 C10 1.395(5) . ? 
C9 C12 1.481(4) . ? 
C10 C11 1.392(5) . ? 
C12 C17 1.396(5) . ? 
C12 C13 1.400(5) . ? 
C13 C14 1.387(5) . ? 
C14 C15 1.397(5) . ? 
C15 C16 1.407(4) . ? 
C16 C17 1.386(5) . ? 
C18 C23 1.386(5) . ? 
C18 C19 1.396(5) . ? 
C19 C20 1.395(6) . ? 
C20 C21 1.377(7) . ? 
C21 C22 1.393(7) . ? 
C22 C23 1.395(5) . ? 
C24 C29 1.392(5) . ? 
C24 C25 1.396(5) . ? 
C25 C26 1.396(5) . ? 
C26 C27 1.380(6) . ? 
C27 C28 1.393(6) . ? 
C28 C29 1.387(5) . ? 
  
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 
C5 N1 C1 120.6(4) . . ? 
C5 N1 C35 120.5(4) . . ? 
C1 N1 C35 118.8(4) . . ? 
C15 N2 C18 120.5(3) . . ? 
C15 N2 C24 121.2(3) . . ? 
C18 N2 C24 118.0(3) . . ? 
N1 C1 C2 120.6(5) . . ? 
C1 C2 C3 120.5(4) . . ? 
C2 C3 C4 117.1(4) . . ? 
C2 C3 C6 122.2(4) . . ? 
C4 C3 C6 120.7(4) . . ? 
C5 C4 C3 119.7(4) . . ? 
N1 C5 C4 121.4(4) . . ? 
C7 C6 C11 118.7(3) . . ? 
C7 C6 C3 120.7(4) . . ? 
C11 C6 C3 120.6(4) . . ? 
C6 C7 C8 120.8(4) . . ? 
C7 C8 C9 121.1(4) . . ? 
C10 C9 C8 117.5(3) . . ? 
C10 C9 C12 121.6(3) . . ? 
C8 C9 C12 120.9(3) . . ? 
C11 C10 C9 121.4(3) . . ? 
C10 C11 C6 120.5(4) . . ? 
C17 C12 C13 117.1(3) . . ? 
C17 C12 C9 122.0(3) . . ? 
C13 C12 C9 120.9(3) . . ? 
C14 C13 C12 121.7(3) . . ? 
C13 C14 C15 120.6(3) . . ? 
C14 C15 C16 118.3(3) . . ? 
C14 C15 N2 120.8(3) . . ? 
C16 C15 N2 120.9(3) . . ? 
C17 C16 C15 120.1(3) . . ? 
C16 C17 C12 122.1(3) . . ? 
C23 C18 C19 119.8(3) . . ? 
C23 C18 N2 120.2(3) . . ? 
C19 C18 N2 120.0(3) . . ? 
C20 C19 C18 119.6(4) . . ? 
C21 C20 C19 120.7(4) . . ? 
C20 C21 C22 119.8(4) . . ? 
C21 C22 C23 120.0(4) . . ? 
C18 C23 C22 120.1(3) . . ? 
C29 C24 C25 119.4(3) . . ? 
C29 C24 N2 119.7(3) . . ? 
C25 C24 N2 120.9(3) . . ? 
C24 C25 C26 119.7(3) . . ? 
C27 C26 C25 120.7(4) . . ? 
C26 C27 C28 119.5(3) . . ? 
C29 C28 C27 120.3(4) . . ? 
C28 C29 C24 120.4(3) . . ? 
  
_refine_diff_density_max    0.674 
_refine_diff_density_min   -1.782 
_refine_diff_density_rms    0.129 
  
  
  
