# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1905975'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 I2 O P'
_chemical_formula_weight         584.14

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   ' p_n_a_21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.5490(16)
_cell_length_b                   9.8719(8)
_cell_length_c                   10.8488(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2093.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9713
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20543
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3647
_reflns_number_gt                3599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+4.1697P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0156(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(3)
_refine_ls_number_reflns         3647
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.412204(19) 0.33529(5) 0.63945(5) 0.04516(18) Uani 1 1 d . . .
I2 I 0.43217(4) 0.01711(6) 0.42523(7) 0.0743(3) Uani 1 1 d . . .
P1 P 0.63971(8) 0.18385(14) 0.55712(14) 0.0277(3) Uani 1 1 d . . .
O1 O 0.6334(2) 0.0345(4) 0.5698(5) 0.0399(10) Uani 1 1 d . . .
C1 C 0.7036(3) 0.2525(6) 0.6611(5) 0.0299(12) Uani 1 1 d . . .
C13 C 0.5602(3) 0.2757(5) 0.5928(5) 0.0258(11) Uani 1 1 d . . .
C14 C 0.5698(3) 0.4255(5) 0.6122(5) 0.0256(11) Uani 1 1 d . . .
C19 C 0.5778(3) 0.4789(6) 0.7306(6) 0.0301(12) Uani 1 1 d . . .
C21 C 0.5001(3) 0.2161(6) 0.6007(5) 0.0316(12) Uani 1 1 d . . .
C15 C 0.5688(3) 0.5124(6) 0.5108(6) 0.0332(12) Uani 1 1 d . . .
H15 H 0.5636 0.4764 0.4301 0.040 Uiso 1 1 calc R . .
C2 C 0.7292(3) 0.3813(7) 0.6581(6) 0.0361(13) Uani 1 1 d . . .
H2 H 0.7172 0.4397 0.5918 0.043 Uiso 1 1 calc R . .
C7 C 0.6591(3) 0.2399(6) 0.4031(6) 0.0358(14) Uani 1 1 d . . .
C22 C 0.4834(4) 0.0692(7) 0.5927(7) 0.0456(16) Uani 1 1 d . . .
H22A H 0.4541 0.0440 0.6635 0.055 Uiso 1 1 calc R . .
H22B H 0.5263 0.0162 0.5989 0.055 Uiso 1 1 calc R . .
C8 C 0.6083(4) 0.2402(7) 0.3152(6) 0.0396(14) Uani 1 1 d . . .
H8 H 0.5633 0.2143 0.3388 0.047 Uiso 1 1 calc R . .
C17 C 0.5837(3) 0.7026(6) 0.6415(10) 0.0448(15) Uani 1 1 d . . .
H17 H 0.5888 0.7975 0.6525 0.054 Uiso 1 1 calc R . .
C18 C 0.5846(3) 0.6201(7) 0.7408(7) 0.0384(15) Uani 1 1 d . . .
H18 H 0.5901 0.6590 0.8203 0.046 Uiso 1 1 calc R . .
C16 C 0.5755(4) 0.6520(6) 0.5273(8) 0.0393(17) Uani 1 1 d . . .
H16 H 0.5742 0.7110 0.4582 0.047 Uiso 1 1 calc R . .
C20 C 0.5807(4) 0.3902(7) 0.8435(6) 0.0445(16) Uani 1 1 d . . .
H20A H 0.6256 0.3994 0.8828 0.067 Uiso 1 1 calc R . .
H20B H 0.5734 0.2956 0.8196 0.067 Uiso 1 1 calc R . .
H20C H 0.5449 0.4180 0.9015 0.067 Uiso 1 1 calc R . .
C4 C 0.7896(4) 0.3461(9) 0.8444(8) 0.054(2) Uani 1 1 d . . .
H4 H 0.8192 0.3782 0.9074 0.064 Uiso 1 1 calc R . .
C11 C 0.6199(5) 0.2763(9) 0.1953(7) 0.058(2) Uani 1 1 d . . .
H11 H 0.5834 0.2784 0.1374 0.070 Uiso 1 1 calc R . .
C9 C 0.7264(4) 0.2731(7) 0.3679(7) 0.0429(15) Uani 1 1 d . . .
H9 H 0.7625 0.2733 0.4266 0.052 Uiso 1 1 calc R . .
C5 C 0.7648(4) 0.2171(9) 0.8494(7) 0.0484(17) Uani 1 1 d . . .
H5 H 0.7772 0.1600 0.9163 0.058 Uiso 1 1 calc R . .
C12 C 0.6876(5) 0.3105(8) 0.1593(7) 0.060(2) Uani 1 1 d . . .
H12 H 0.6973 0.3363 0.0768 0.072 Uiso 1 1 calc R . .
C3 C 0.7723(4) 0.4283(8) 0.7500(7) 0.0490(18) Uani 1 1 d . . .
H3 H 0.7896 0.5181 0.7466 0.059 Uiso 1 1 calc R . .
C6 C 0.7212(3) 0.1676(6) 0.7575(6) 0.0391(14) Uani 1 1 d . . .
H6 H 0.7041 0.0776 0.7611 0.047 Uiso 1 1 calc R . .
C10 C 0.7388(5) 0.3056(8) 0.2457(8) 0.056(2) Uani 1 1 d . . .
H10 H 0.7843 0.3251 0.2208 0.068 Uiso 1 1 calc R . .


_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
I1 C21 2.124(6) . ?
I2 C22 2.138(7) . ?
P1 O1 1.486(4) . ?
P1 C7 1.801(6) . ?
P1 C1 1.814(6) . ?
P1 C13 1.840(6) . ?
C1 C2 1.367(9) . ?
C1 C6 1.384(9) . ?
C13 C21 1.318(8) . ?
C13 C14 1.505(7) . ?
C14 C15 1.396(9) . ?
C14 C19 1.397(9) . ?
C19 C18 1.405(9) . ?
C19 C20 1.507(10) . ?
C21 C22 1.488(9) . ?
C15 C16 1.395(9) . ?
C15 H15 0.9500 . ?
C2 C3 1.385(9) . ?
C2 H2 0.9500 . ?
C7 C8 1.377(10) . ?
C7 C9 1.408(9) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C8 C11 1.367(11) . ?
C8 H8 0.9500 . ?
C17 C16 1.345(13) . ?
C17 C18 1.349(13) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C16 H16 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C4 C3 1.350(12) . ?
C4 C5 1.365(12) . ?
C4 H4 0.9500 . ?
C11 C12 1.422(13) . ?
C11 H11 0.9500 . ?
C9 C10 1.385(12) . ?
C9 H9 0.9500 . ?
C5 C6 1.400(10) . ?
C5 H5 0.9500 . ?
C12 C10 1.371(14) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?

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
O1 P1 C7 114.1(3) . . ?
O1 P1 C1 111.7(3) . . ?
C7 P1 C1 108.5(3) . . ?
O1 P1 C13 113.6(3) . . ?
C7 P1 C13 102.8(3) . . ?
C1 P1 C13 105.5(2) . . ?
C2 C1 C6 119.3(6) . . ?
C2 C1 P1 125.8(5) . . ?
C6 C1 P1 114.6(5) . . ?
C21 C13 C14 122.8(5) . . ?
C21 C13 P1 123.2(4) . . ?
C14 C13 P1 114.1(4) . . ?
C15 C14 C19 119.6(5) . . ?
C15 C14 C13 119.4(5) . . ?
C19 C14 C13 120.9(5) . . ?
C14 C19 C18 117.2(6) . . ?
C14 C19 C20 122.1(5) . . ?
C18 C19 C20 120.6(6) . . ?
C13 C21 C22 128.8(6) . . ?
C13 C21 I1 119.1(4) . . ?
C22 C21 I1 112.0(4) . . ?
C16 C15 C14 120.3(6) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C1 C2 C3 121.1(6) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C8 C7 C9 119.1(6) . . ?
C8 C7 P1 119.4(5) . . ?
C9 C7 P1 121.3(5) . . ?
C21 C22 I2 112.7(4) . . ?
C21 C22 H22A 109.1 . . ?
I2 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
I2 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C11 C8 C7 122.6(7) . . ?
C11 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C16 C17 C18 120.8(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 122.3(7) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C17 C16 C15 119.7(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
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 . . ?
C3 C4 C5 120.1(7) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C8 C11 C12 118.5(8) . . ?
C8 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C10 C9 C7 118.5(7) . . ?
C10 C9 H9 120.8 . . ?
C7 C9 H9 120.8 . . ?
C4 C5 C6 120.9(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C10 C12 C11 118.9(7) . . ?
C10 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C1 C6 C5 118.7(6) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C12 C10 C9 122.3(7) . . ?
C12 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.105
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound16
_database_code_depnum_ccdc_archive 'CCDC 1905978'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 I N3 O2 P'
_chemical_formula_weight         515.27

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'
P P 0.2955 0.4335 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.3026(2)
_cell_length_b                   8.5630(2)
_cell_length_c                   30.1250(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2141.75(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3036
_cell_measurement_theta_min      4.4130
_cell_measurement_theta_max      71.8050

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    12.643
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5368
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         71.91
_reflns_number_total             3737
_reflns_number_gt                3622
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0948P)²+0.0000P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(9)
_refine_ls_number_reflns         3737
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.01974(5) -0.20631(5) 0.075538(12) 0.03298(14) Uani 1 1 d . . .
P1 P 0.53232(18) -0.06682(16) 0.09893(5) 0.0249(3) Uani 1 1 d . . .
O1 O 0.6188(5) -0.2035(6) 0.07941(16) 0.0352(9) Uani 1 1 d . . .
C13 C 0.3111(7) -0.0855(7) 0.09782(19) 0.0219(11) Uani 1 1 d . . .
C19 C 0.0334(9) 0.2307(9) 0.1773(2) 0.0389(15) Uani 1 1 d . . .
C18 C 0.0902(9) 0.2797(7) 0.1366(2) 0.0383(14) Uani 1 1 d . . .
H18 H 0.0670 0.3795 0.1262 0.046 Uiso 1 1 calc R . .
C16 C 0.2203(7) 0.0286(7) 0.1254(2) 0.0249(11) Uani 1 1 d . . .
C20 C 0.0717(10) 0.0824(9) 0.1921(2) 0.0398(16) Uani 1 1 d . . .
H20 H 0.0338 0.0492 0.2196 0.048 Uiso 1 1 calc R . .
C17 C 0.1837(8) 0.1765(7) 0.1111(2) 0.0310(13) Uani 1 1 d . . .
H17 H 0.2220 0.2095 0.0836 0.037 Uiso 1 1 calc R . .
C2 C 0.6798(11) 0.2238(10) 0.0867(3) 0.0478(18) Uani 1 1 d . . .
H2 H 0.7341 0.2050 0.1132 0.057 Uiso 1 1 calc R . .
C21 C 0.1644(9) -0.0165(9) 0.1672(2) 0.0368(15) Uani 1 1 d . . .
H21 H 0.1903 -0.1148 0.1782 0.044 Uiso 1 1 calc R . .
O2 O -0.0599(8) 0.3181(8) 0.2048(2) 0.0612(17) Uani 1 1 d . . .
C1 C 0.5725(7) 0.1153(7) 0.0710(2) 0.0301(12) Uani 1 1 d . . .
C6 C 0.5027(10) 0.1395(11) 0.0297(2) 0.0483(18) Uani 1 1 d . . .
H6 H 0.4368 0.0638 0.0171 0.058 Uiso 1 1 calc R . .
C3 C 0.7081(13) 0.3605(10) 0.0638(3) 0.055(2) Uani 1 1 d . . .
H3 H 0.7799 0.4335 0.0753 0.066 Uiso 1 1 calc R . .
C5 C 0.5334(11) 0.2808(13) 0.0071(3) 0.062(2) Uani 1 1 d . . .
H5 H 0.4846 0.2986 -0.0202 0.075 Uiso 1 1 calc R . .
C7 C 0.5847(8) -0.0404(8) 0.1567(2) 0.0305(13) Uani 1 1 d . . .
C12 C 0.5442(10) 0.0936(10) 0.1814(3) 0.0452(17) Uani 1 1 d . . .
H12 H 0.4874 0.1753 0.1684 0.054 Uiso 1 1 calc R . .
C8 C 0.6703(10) -0.1613(9) 0.1763(2) 0.0397(16) Uani 1 1 d . . .
H8 H 0.6985 -0.2489 0.1598 0.048 Uiso 1 1 calc R . .
C11 C 0.5914(11) 0.1012(12) 0.2259(3) 0.057(2) Uani 1 1 d . . .
H11 H 0.5664 0.1891 0.2427 0.068 Uiso 1 1 calc R . .
C4 C 0.6313(11) 0.3899(11) 0.0242(3) 0.053(2) Uani 1 1 d . . .
H4 H 0.6471 0.4842 0.0095 0.064 Uiso 1 1 calc R . .
C10 C 0.6746(14) -0.0207(15) 0.2452(3) 0.064(3) Uani 1 1 d . . .
H10 H 0.7044 -0.0143 0.2749 0.077 Uiso 1 1 calc R . .
C14 C 0.2342(6) -0.1927(7) 0.07401(19) 0.0251(11) Uani 1 1 d . . .
C9 C 0.7141(12) -0.1510(12) 0.2212(3) 0.058(2) Uani 1 1 d . . .
H9 H 0.7698 -0.2325 0.2346 0.070 Uiso 1 1 calc R . .
C22 C -0.1241(17) 0.4587(16) 0.1895(4) 0.087(5) Uani 1 1 d . . .
H22A H -0.0399 0.5351 0.1872 0.131 Uiso 1 1 calc R . .
H22B H -0.2047 0.4950 0.2099 0.131 Uiso 1 1 calc R . .
H22C H -0.1720 0.4428 0.1608 0.131 Uiso 1 1 calc R . .
N1 N 0.3001(9) -0.4742(7) 0.0717(3) 0.0498(16) Uani 1 1 d . . .
C15 C 0.3076(8) -0.3242(8) 0.0470(2) 0.0335(13) Uani 1 1 d . . .
H15A H 0.2500 -0.3346 0.0192 0.040 Uiso 1 1 calc R . .
H15B H 0.4190 -0.2995 0.0403 0.040 Uiso 1 1 calc R . .
N2 N 0.3731(9) -0.4704(8) 0.1077(3) 0.0500(17) Uani 1 1 d . . .
N3 N 0.4337(16) -0.4842(12) 0.1407(3) 0.083(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
I1 C14 2.112(5) . ?
P1 O1 1.494(5) . ?
P1 C1 1.804(6) . ?
P1 C7 1.807(7) . ?
P1 C13 1.844(6) . ?
C13 C14 1.329(8) . ?
C13 C16 1.488(8) . ?
C19 O2 1.359(9) . ?
C19 C18 1.378(11) . ?
C19 C20 1.384(11) . ?
C18 C17 1.406(10) . ?
C16 C17 1.372(9) . ?
C16 C21 1.395(9) . ?
C20 C21 1.369(10) . ?
C2 C1 1.372(10) . ?
C2 C3 1.379(11) . ?
O2 C22 1.396(14) . ?
C1 C6 1.387(9) . ?
C6 C5 1.411(12) . ?
C3 C4 1.375(13) . ?
C5 C4 1.342(14) . ?
C7 C8 1.389(10) . ?
C7 C12 1.409(10) . ?
C12 C11 1.397(11) . ?
C8 C9 1.402(11) . ?
C11 C10 1.380(15) . ?
C10 C9 1.368(16) . ?
C14 C15 1.516(9) . ?
N1 N2 1.244(11) . ?
N1 C15 1.485(10) . ?
N2 N3 1.119(12) . ?

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
O1 P1 C1 113.9(3) . . ?
O1 P1 C7 111.2(3) . . ?
C1 P1 C7 107.3(3) . . ?
O1 P1 C13 113.8(3) . . ?
C1 P1 C13 104.5(3) . . ?
C7 P1 C13 105.5(3) . . ?
C14 C13 C16 120.8(5) . . ?
C14 C13 P1 123.2(4) . . ?
C16 C13 P1 116.0(4) . . ?
O2 C19 C18 124.8(7) . . ?
O2 C19 C20 116.0(7) . . ?
C18 C19 C20 119.2(6) . . ?
C19 C18 C17 119.0(6) . . ?
C17 C16 C21 117.7(6) . . ?
C17 C16 C13 122.8(6) . . ?
C21 C16 C13 119.4(6) . . ?
C21 C20 C19 121.3(7) . . ?
C16 C17 C18 122.0(6) . . ?
C1 C2 C3 120.9(8) . . ?
C20 C21 C16 120.8(7) . . ?
C19 O2 C22 119.4(8) . . ?
C2 C1 C6 118.7(6) . . ?
C2 C1 P1 123.0(5) . . ?
C6 C1 P1 118.1(5) . . ?
C1 C6 C5 119.0(8) . . ?
C4 C3 C2 120.7(8) . . ?
C4 C5 C6 121.4(8) . . ?
C8 C7 C12 120.3(6) . . ?
C8 C7 P1 116.1(5) . . ?
C12 C7 P1 123.6(5) . . ?
C11 C12 C7 118.6(8) . . ?
C7 C8 C9 119.8(7) . . ?
C10 C11 C12 120.5(8) . . ?
C5 C4 C3 119.1(8) . . ?
C9 C10 C11 121.0(7) . . ?
C13 C14 C15 127.5(5) . . ?
C13 C14 I1 120.4(4) . . ?
C15 C14 I1 111.9(4) . . ?
C10 C9 C8 119.9(8) . . ?
N2 N1 C15 113.2(6) . . ?
N1 C15 C14 110.9(5) . . ?
N3 N2 N1 172.1(9) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        71.91
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         1.801
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.137
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound15
_database_code_depnum_ccdc_archive 'CCDC 1905977'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 I N3 O P'
_chemical_formula_weight         499.27

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.209(3)
_cell_length_b                   16.624(7)
_cell_length_c                   15.715(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.215(6)
_cell_angle_gamma                90.00
_cell_volume                     2142.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5089
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.75

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    1.586
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19650
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         24.85
_reflns_number_total             3686
_reflns_number_gt                3417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.8814P] where P=(Fo²+2Fc²)/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         3686
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.438478(19) 0.720733(11) 0.302151(12) 0.05009(9) Uani 1 1 d . . .
P1 P 0.11615(8) 0.79130(4) 0.26009(4) 0.03605(15) Uani 1 1 d . . .
O1 O 0.2003(2) 0.71569(10) 0.28652(13) 0.0463(5) Uani 1 1 d . . .
C3 C 0.2855(4) 0.77950(19) 0.02216(19) 0.0549(8) Uani 1 1 d . . .
H3 H 0.3368 0.7409 -0.0102 0.066 Uiso 1 1 calc R . .
C6 C 0.1325(3) 0.89429(16) 0.11799(16) 0.0438(6) Uani 1 1 d . . .
H6 H 0.0811 0.9333 0.1498 0.053 Uiso 1 1 calc R . .
C1 C 0.1656(3) 0.81956(15) 0.15313(15) 0.0368(5) Uani 1 1 d . . .
C2 C 0.2431(3) 0.76153(17) 0.10524(18) 0.0459(6) Uani 1 1 d . . .
H2 H 0.2664 0.7112 0.1284 0.055 Uiso 1 1 calc R . .
C10 C 0.2856(5) 0.9864(3) 0.4481(2) 0.0811(11) Uani 1 1 d . . .
H10 H 0.3237 1.0242 0.4877 0.097 Uiso 1 1 calc R . .
C7 C 0.1719(3) 0.87426(17) 0.32963(16) 0.0428(6) Uani 1 1 d . . .
C9 C 0.3549(4) 0.9810(2) 0.3704(2) 0.0798(11) Uani 1 1 d . . .
H9 H 0.4392 1.0157 0.3573 0.096 Uiso 1 1 calc R . .
C8 C 0.3007(4) 0.9246(2) 0.31144(19) 0.0585(8) Uani 1 1 d . . .
H8 H 0.3506 0.9204 0.2595 0.070 Uiso 1 1 calc R . .
C5 C 0.1756(3) 0.91133(18) 0.03550(17) 0.0508(7) Uani 1 1 d . . .
H5 H 0.1531 0.9617 0.0121 0.061 Uiso 1 1 calc R . .
C4 C 0.2516(3) 0.8537(2) -0.01170(17) 0.0524(7) Uani 1 1 d . . .
H4 H 0.2802 0.8654 -0.0671 0.063 Uiso 1 1 calc R . .
C11 C 0.1027(4) 0.88092(19) 0.40845(18) 0.0552(7) Uani 1 1 d . . .
H11 H 0.0162 0.8476 0.4216 0.066 Uiso 1 1 calc R . .
C12 C -0.1068(3) 0.78484(14) 0.26148(16) 0.0368(5) Uani 1 1 d . . .
C13 C -0.1816(3) 0.72763(15) 0.30579(16) 0.0381(6) Uani 1 1 d . . .
C17 C -0.1027(3) 0.66144(17) 0.35736(18) 0.0487(7) Uani 1 1 d . . .
H17A H 0.0089 0.6764 0.3725 0.058 Uiso 1 1 calc R . .
H17B H -0.1602 0.6546 0.4097 0.058 Uiso 1 1 calc R . .
C15 C -0.2267(3) 0.92119(17) 0.2475(2) 0.0551(7) Uani 1 1 d . . .
H15 H -0.1851 0.9318 0.3023 0.066 Uiso 1 1 calc R . .
C14 C -0.1995(3) 0.84719(16) 0.21092(17) 0.0427(6) Uani 1 1 d . . .
C16 C -0.2604(3) 0.83062(19) 0.12804(19) 0.0537(7) Uani 1 1 d . . .
N2 N -0.0408(3) 0.58736(15) 0.2410(2) 0.0650(7) Uani 1 1 d . . .
N1 N -0.1034(4) 0.58465(16) 0.3106(2) 0.0725(8) Uani 1 1 d . . .
N3 N 0.0109(5) 0.5825(2) 0.1759(2) 0.0906(10) Uani 1 1 d . . .
C18 C 0.1604(5) 0.9362(2) 0.46748(19) 0.0708(10) Uani 1 1 d . . .
H18 H 0.1143 0.9393 0.5205 0.085 Uiso 1 1 calc R . .
C19 C -0.2347(4) 0.7522(2) 0.0850(2) 0.0697(9) Uani 1 1 d . . .
H19A H -0.1202 0.7438 0.0785 0.105 Uiso 1 1 calc R . .
H19B H -0.2897 0.7527 0.0300 0.105 Uiso 1 1 calc R . .
H19C H -0.2777 0.7097 0.1188 0.105 Uiso 1 1 calc R . .
C20 C -0.3504(4) 0.8908(2) 0.0861(2) 0.0689(10) Uani 1 1 d . . .
H20 H -0.3929 0.8810 0.0314 0.083 Uiso 1 1 calc R . .
C22 C -0.3161(4) 0.9802(2) 0.2032(3) 0.0724(10) Uani 1 1 d . . .
H22 H -0.3336 1.0302 0.2278 0.087 Uiso 1 1 calc R . .
C21 C -0.3779(4) 0.9632(2) 0.1228(3) 0.0790(12) Uani 1 1 d . . .
H21 H -0.4393 1.0018 0.0930 0.095 Uiso 1 1 calc R . .


_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
I1 C13 2.110(3) . ?
P1 O1 1.4859(18) . ?
P1 C1 1.807(2) . ?
P1 C7 1.808(3) . ?
P1 C12 1.835(3) . ?
C3 C4 1.368(4) . ?
C3 C2 1.396(4) . ?
C6 C1 1.382(4) . ?
C6 C5 1.386(4) . ?
C1 C2 1.392(4) . ?
C10 C18 1.367(5) . ?
C10 C9 1.370(5) . ?
C7 C8 1.387(4) . ?
C7 C11 1.387(4) . ?
C9 C8 1.380(4) . ?
C5 C4 1.375(4) . ?
C11 C18 1.376(5) . ?
C12 C13 1.341(3) . ?
C12 C14 1.496(3) . ?
C13 C17 1.499(3) . ?
C17 N1 1.473(4) . ?
C15 C14 1.380(4) . ?
C15 C22 1.394(4) . ?
C14 C16 1.404(4) . ?
C16 C20 1.394(4) . ?
C16 C19 1.487(5) . ?
N2 N3 1.126(4) . ?
N2 N1 1.226(4) . ?
C20 C21 1.358(6) . ?
C22 C21 1.374(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
O1 P1 C1 111.17(12) . . ?
O1 P1 C7 111.86(12) . . ?
C1 P1 C7 107.66(12) . . ?
O1 P1 C12 113.61(11) . . ?
C1 P1 C12 106.66(11) . . ?
C7 P1 C12 105.49(12) . . ?
C4 C3 C2 120.2(3) . . ?
C1 C6 C5 120.3(3) . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 P1 123.88(19) . . ?
C2 C1 P1 116.5(2) . . ?
C1 C2 C3 119.5(3) . . ?
C18 C10 C9 120.0(3) . . ?
C8 C7 C11 118.5(3) . . ?
C8 C7 P1 120.9(2) . . ?
C11 C7 P1 119.9(2) . . ?
C10 C9 C8 120.5(4) . . ?
C9 C8 C7 120.0(3) . . ?
C4 C5 C6 120.0(3) . . ?
C3 C4 C5 120.5(3) . . ?
C18 C11 C7 120.9(3) . . ?
C13 C12 C14 122.2(2) . . ?
C13 C12 P1 121.65(19) . . ?
C14 C12 P1 116.11(17) . . ?
C12 C13 C17 127.2(2) . . ?
C12 C13 I1 120.09(18) . . ?
C17 C13 I1 112.67(17) . . ?
N1 C17 C13 111.9(2) . . ?
C14 C15 C22 120.6(3) . . ?
C15 C14 C16 120.3(3) . . ?
C15 C14 C12 118.9(2) . . ?
C16 C14 C12 120.8(3) . . ?
C20 C16 C14 117.4(3) . . ?
C20 C16 C19 119.7(3) . . ?
C14 C16 C19 122.8(3) . . ?
N3 N2 N1 173.2(3) . . ?
N2 N1 C17 114.8(2) . . ?
C10 C18 C11 120.0(3) . . ?
C21 C20 C16 122.0(3) . . ?
C21 C22 C15 118.9(3) . . ?
C20 C21 C22 120.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.85
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.076
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound14
_database_code_depnum_ccdc_archive 'CCDC 1905976'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 I N3 O P'
_chemical_formula_weight         485.25

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1543(3)
_cell_length_b                   10.0610(4)
_cell_length_c                   22.0753(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.464(3)
_cell_angle_gamma                90.00
_cell_volume                     2032.48(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3799
_cell_measurement_theta_min      3.9860
_cell_measurement_theta_max      71.6340

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    13.245
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7675
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         71.83
_reflns_number_total             3907
_reflns_number_gt                3467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1455P)²+2.5879P] where P=(Fo²+2Fc²)/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         3907
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.1985
_refine_ls_wR_factor_gt          0.1900
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.12861(4) 0.05401(4) 0.39628(2) 0.0469(2) Uani 1 1 d . . .
P1 P 0.89133(14) 0.44341(10) 0.31848(5) 0.0244(3) Uani 1 1 d . . .
C19 C 0.9462(5) 0.2917(4) 0.3591(2) 0.0240(9) Uani 1 1 d . . .
C14 C 0.8121(6) 0.5528(4) 0.3739(2) 0.0269(10) Uani 1 1 d . . .
C20 C 1.0688(5) 0.2261(5) 0.3466(2) 0.0297(10) Uani 1 1 d . . .
C8 C 0.8443(5) 0.2445(5) 0.4062(2) 0.0292(10) Uani 1 1 d . . .
C4 C 0.6191(7) 0.4669(6) 0.2595(3) 0.0383(12) Uani 1 1 d . . .
H4 H 0.6070 0.5439 0.2822 0.046 Uiso 1 1 calc R . .
C15 C 0.6864(6) 0.5260(5) 0.4046(3) 0.0338(11) Uani 1 1 d . . .
H15 H 0.6360 0.4472 0.3971 0.041 Uiso 1 1 calc R . .
C3 C 0.5135(9) 0.4303(8) 0.2173(3) 0.0555(18) Uani 1 1 d . . .
H3 H 0.4304 0.4824 0.2115 0.067 Uiso 1 1 calc R . .
C13 C 0.8863(6) 0.6719(6) 0.3851(3) 0.0382(12) Uani 1 1 d . . .
H13 H 0.9708 0.6916 0.3644 0.046 Uiso 1 1 calc R . .
C5 C 0.7442(6) 0.3894(5) 0.2687(2) 0.0280(10) Uani 1 1 d . . .
C6 C 0.7612(8) 0.2744(6) 0.2339(3) 0.0415(13) Uani 1 1 d . . .
H6 H 0.8438 0.2215 0.2393 0.050 Uiso 1 1 calc R . .
C12 C 0.7705(8) 0.2348(8) 0.5091(3) 0.0554(18) Uani 1 1 d . . .
H12 H 0.7868 0.2565 0.5497 0.067 Uiso 1 1 calc R . .
C7 C 0.8661(7) 0.2808(6) 0.4661(3) 0.0397(12) Uani 1 1 d . . .
H7 H 0.9440 0.3355 0.4775 0.048 Uiso 1 1 calc R . .
C17 C 0.7097(8) 0.7335(7) 0.4575(3) 0.0487(15) Uani 1 1 d . . .
H17 H 0.6747 0.7938 0.4855 0.058 Uiso 1 1 calc R . .
C9 C 0.7242(7) 0.1658(7) 0.3890(3) 0.0480(15) Uani 1 1 d . . .
H9 H 0.7079 0.1425 0.3486 0.058 Uiso 1 1 calc R . .
C21 C 1.1812(8) 0.2611(8) 0.3010(4) 0.0583(19) Uani 1 1 d . . .
H21A H 1.1948 0.1860 0.2742 0.070 Uiso 1 1 calc R . .
H21B H 1.1460 0.3352 0.2767 0.070 Uiso 1 1 calc R . .
C11 C 0.6531(8) 0.1582(9) 0.4929(4) 0.071(3) Uani 1 1 d . . .
H11 H 0.5889 0.1297 0.5221 0.085 Uiso 1 1 calc R . .
C2 C 0.5308(10) 0.3166(9) 0.1836(3) 0.063(2) Uani 1 1 d . . .
H2 H 0.4586 0.2914 0.1554 0.076 Uiso 1 1 calc R . .
C16 C 0.6348(7) 0.6153(6) 0.4463(3) 0.0388(12) Uani 1 1 d . . .
H16 H 0.5501 0.5965 0.4670 0.047 Uiso 1 1 calc R . .
C18 C 0.8335(8) 0.7610(7) 0.4274(3) 0.0519(16) Uani 1 1 d . . .
H18 H 0.8834 0.8400 0.4352 0.062 Uiso 1 1 calc R . .
N2 N 1.3095(14) 0.3773(15) 0.3664(6) 0.113(6) Uani 1 1 d . . .
N1 N 1.3188(9) 0.2957(18) 0.3290(8) 0.135(6) Uani 1 1 d . . .
C1 C 0.6541(11) 0.2400(8) 0.1913(3) 0.063(2) Uani 1 1 d . . .
H1 H 0.6658 0.1643 0.1677 0.076 Uiso 1 1 calc R . .
C10 C 0.6297(8) 0.1232(9) 0.4331(5) 0.068(2) Uani 1 1 d . . .
H10 H 0.5498 0.0704 0.4223 0.081 Uiso 1 1 calc R . .
O1 O 1.0119(5) 0.5107(4) 0.28645(19) 0.0402(9) Uani 1 1 d . . .
N3 N 1.303(3) 0.4595(18) 0.4046(8) 0.213(13) 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
I1 C20 2.114(5) . ?
P1 O1 1.489(4) . ?
P1 C5 1.800(5) . ?
P1 C14 1.810(5) . ?
P1 C19 1.833(5) . ?
C19 C20 1.336(7) . ?
C19 C8 1.493(6) . ?
C14 C15 1.377(8) . ?
C14 C13 1.397(7) . ?
C20 C21 1.500(8) . ?
C8 C7 1.381(8) . ?
C8 C9 1.400(8) . ?
C4 C3 1.377(10) . ?
C4 C5 1.396(8) . ?
C15 C16 1.379(8) . ?
C3 C2 1.376(13) . ?
C13 C18 1.390(9) . ?
C5 C6 1.399(7) . ?
C6 C1 1.385(10) . ?
C12 C11 1.363(13) . ?
C12 C7 1.387(8) . ?
C17 C18 1.356(11) . ?
C17 C16 1.391(9) . ?
C9 C10 1.388(9) . ?
C21 N1 1.432(16) . ?
C11 C10 1.376(14) . ?
C2 C1 1.374(14) . ?
N2 N1 1.17(2) . ?
N2 N3 1.18(3) . ?

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
O1 P1 C5 113.5(2) . . ?
O1 P1 C14 111.0(2) . . ?
C5 P1 C14 106.8(2) . . ?
O1 P1 C19 114.4(2) . . ?
C5 P1 C19 103.8(2) . . ?
C14 P1 C19 106.6(2) . . ?
C20 C19 C8 121.9(4) . . ?
C20 C19 P1 122.1(4) . . ?
C8 C19 P1 115.9(3) . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 P1 124.6(4) . . ?
C13 C14 P1 116.1(4) . . ?
C19 C20 C21 128.0(5) . . ?
C19 C20 I1 120.4(4) . . ?
C21 C20 I1 111.5(4) . . ?
C7 C8 C9 120.2(5) . . ?
C7 C8 C19 120.4(5) . . ?
C9 C8 C19 119.4(5) . . ?
C3 C4 C5 120.5(6) . . ?
C14 C15 C16 120.4(5) . . ?
C2 C3 C4 120.0(7) . . ?
C18 C13 C14 119.8(6) . . ?
C4 C5 C6 119.0(5) . . ?
C4 C5 P1 121.2(4) . . ?
C6 C5 P1 119.5(4) . . ?
C1 C6 C5 119.5(7) . . ?
C11 C12 C7 121.0(7) . . ?
C8 C7 C12 119.2(6) . . ?
C18 C17 C16 120.1(5) . . ?
C10 C9 C8 118.9(7) . . ?
N1 C21 C20 112.2(8) . . ?
C12 C11 C10 120.0(6) . . ?
C1 C2 C3 120.3(7) . . ?
C15 C16 C17 120.0(6) . . ?
C17 C18 C13 120.4(6) . . ?
N1 N2 N3 178.8(19) . . ?
N2 N1 C21 113.4(11) . . ?
C2 C1 C6 120.6(7) . . ?
C11 C10 C9 120.6(7) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        71.83
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         2.388
_refine_diff_density_min         -2.415
_refine_diff_density_rms         0.214
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound22
_database_code_depnum_ccdc_archive 'CCDC 1905980'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 I N3 O P'
_chemical_formula_weight         601.40

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   8.9643(4)
_cell_length_b                   11.6596(6)
_cell_length_c                   14.2643(7)
_cell_angle_alpha                69.832(2)
_cell_angle_beta                 71.872(2)
_cell_angle_gamma                79.193(2)
_cell_volume                     1324.64(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9090
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45893
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.64
_reflns_number_total             6145
_reflns_number_gt                5466
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.3286P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0202(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6145
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.72608(2) 0.566308(16) 0.503744(11) 0.05627(9) Uani 1 1 d . . .
P1 P 0.79862(5) 0.58082(4) 0.81524(4) 0.03145(11) Uani 1 1 d . . .
O1 O 0.73555(19) 0.46325(14) 0.88665(12) 0.0445(3) Uani 1 1 d . . .
C13 C 0.7826(2) 0.61338(18) 0.68303(14) 0.0324(4) Uani 1 1 d . . .
N1 N 0.6868(2) 0.31576(17) 0.70800(16) 0.0461(4) Uani 1 1 d . . .
C14 C 0.7776(2) 0.74349(18) 0.61768(15) 0.0349(4) Uani 1 1 d . . .
C21 C 0.7782(2) 0.5222(2) 0.64763(15) 0.0375(4) Uani 1 1 d . . .
C15 C 0.9084(2) 0.7854(2) 0.53645(16) 0.0415(4) Uani 1 1 d . . .
H15 H 1.0007 0.7312 0.5250 0.050 Uiso 1 1 calc R . .
C18 C 0.6451(3) 0.8255(2) 0.63295(16) 0.0433(5) Uani 1 1 d . . .
H18 H 0.5547 0.7989 0.6882 0.052 Uiso 1 1 calc R . .
C1 C 0.6929(2) 0.70919(19) 0.85779(15) 0.0360(4) Uani 1 1 d . . .
C7 C 1.0027(2) 0.58976(18) 0.80216(15) 0.0348(4) Uani 1 1 d . . .
N3 N 0.5681(3) 0.2058(2) 0.6667(2) 0.0647(6) Uani 1 1 d . . .
N2 N 0.7028(3) 0.2515(2) 0.6427(2) 0.0653(6) Uani 1 1 d . . .
C8 C 1.1209(2) 0.5703(2) 0.71795(18) 0.0441(5) Uani 1 1 d . . .
H8 H 1.0950 0.5564 0.6633 0.053 Uiso 1 1 calc R . .
C12 C 1.3157(3) 0.5900(2) 0.7927(2) 0.0524(6) Uani 1 1 d . . .
H12 H 1.4231 0.5902 0.7893 0.063 Uiso 1 1 calc R . .
C17 C 0.6432(3) 0.9446(2) 0.56901(19) 0.0502(5) Uani 1 1 d . . .
H17 H 0.5519 0.9996 0.5813 0.060 Uiso 1 1 calc R . .
C6 C 0.5440(3) 0.6916(2) 0.92615(17) 0.0442(5) Uani 1 1 d . . .
H6 H 0.5049 0.6131 0.9523 0.053 Uiso 1 1 calc R . .
C22 C 0.8126(3) 0.3869(2) 0.6955(2) 0.0464(5) Uani 1 1 d . . .
H22A H 0.9113 0.3580 0.6514 0.056 Uiso 1 1 calc R . .
H22B H 0.8295 0.3722 0.7642 0.056 Uiso 1 1 calc R . .
C23 C 0.5427(3) 0.3111(2) 0.77354(18) 0.0459(5) Uani 1 1 d . . .
H23 H 0.5022 0.3489 0.8268 0.055 Uiso 1 1 calc R . .
C16 C 0.9053(3) 0.9046(2) 0.47264(18) 0.0499(5) Uani 1 1 d . . .
H16 H 0.9959 0.9318 0.4178 0.060 Uiso 1 1 calc R . .
C24 C 0.4664(3) 0.2405(2) 0.74781(19) 0.0470(5) Uani 1 1 d . . .
C9 C 1.0427(3) 0.6091(3) 0.88101(18) 0.0522(6) Uani 1 1 d . . .
H9 H 0.9620 0.6231 0.9386 0.063 Uiso 1 1 calc R . .
C10 C 1.2777(3) 0.5712(2) 0.7140(2) 0.0528(6) Uani 1 1 d . . .
H10 H 1.3588 0.5587 0.6561 0.063 Uiso 1 1 calc R . .
C19 C 0.7723(3) 0.9859(2) 0.48700(19) 0.0513(6) Uani 1 1 d . . .
C2 C 0.7505(3) 0.8233(2) 0.82238(19) 0.0501(5) Uani 1 1 d . . .
H2 H 0.8537 0.8350 0.7776 0.060 Uiso 1 1 calc R . .
C11 C 1.1993(3) 0.6086(3) 0.8771(2) 0.0597(7) Uani 1 1 d . . .
H11 H 1.2261 0.6209 0.9322 0.072 Uiso 1 1 calc R . .
C25 C 0.3059(3) 0.2026(2) 0.7926(2) 0.0510(5) Uani 1 1 d . . .
C5 C 0.4528(3) 0.7897(3) 0.9560(2) 0.0613(7) Uani 1 1 d . . .
H5 H 0.3510 0.7781 1.0029 0.074 Uiso 1 1 calc R . .
C3 C 0.6565(4) 0.9202(3) 0.8528(2) 0.0664(7) Uani 1 1 d . . .
H3 H 0.6948 0.9988 0.8281 0.080 Uiso 1 1 calc R . .
C4 C 0.5077(4) 0.9020(3) 0.9188(3) 0.0706(8) Uani 1 1 d . . .
H4 H 0.4429 0.9688 0.9384 0.085 Uiso 1 1 calc R . .
C20 C 0.7675(4) 1.1167(3) 0.4171(3) 0.0785(10) Uani 1 1 d . . .
H20A H 0.7028 1.1702 0.4574 0.118 Uiso 1 1 calc R . .
H20B H 0.7218 1.1225 0.3614 0.118 Uiso 1 1 calc R . .
H20C H 0.8748 1.1423 0.3872 0.118 Uiso 1 1 calc R . .
C30 C 0.2498(4) 0.1359(4) 0.7498(3) 0.0790(9) Uani 1 1 d . . .
H30 H 0.3142 0.1162 0.6896 0.095 Uiso 1 1 calc R . .
C28 C 0.0038(4) 0.1273(4) 0.8781(3) 0.0845(10) Uani 1 1 d . . .
H28 H -0.1000 0.1021 0.9073 0.101 Uiso 1 1 calc R . .
C29 C 0.0990(5) 0.0973(4) 0.7947(3) 0.0919(11) Uani 1 1 d . . .
H29 H 0.0626 0.0489 0.7661 0.110 Uiso 1 1 calc R . .
C26 C 0.2073(4) 0.2319(3) 0.8780(3) 0.0860(11) Uani 1 1 d . . .
H26 H 0.2430 0.2789 0.9083 0.103 Uiso 1 1 calc R . .
C27 C 0.0582(4) 0.1944(4) 0.9202(4) 0.1032(15) Uani 1 1 d . . .
H27 H -0.0081 0.2153 0.9795 0.124 Uiso 1 1 calc R . .


_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
I1 C21 2.115(2) . ?
P1 O1 1.4852(15) . ?
P1 C7 1.7994(19) . ?
P1 C1 1.801(2) . ?
P1 C13 1.8374(19) . ?
C13 C21 1.336(3) . ?
C13 C14 1.483(3) . ?
N1 C23 1.336(3) . ?
N1 N2 1.344(3) . ?
N1 C22 1.454(3) . ?
C14 C18 1.389(3) . ?
C14 C15 1.391(3) . ?
C21 C22 1.502(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C18 C17 1.375(3) . ?
C18 H18 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C6 1.389(3) . ?
C7 C9 1.379(3) . ?
C7 C8 1.387(3) . ?
N3 N2 1.310(3) . ?
N3 C24 1.364(3) . ?
C8 C10 1.390(3) . ?
C8 H8 0.9500 . ?
C12 C10 1.363(4) . ?
C12 C11 1.379(4) . ?
C12 H12 0.9500 . ?
C17 C19 1.385(4) . ?
C17 H17 0.9500 . ?
C6 C5 1.388(3) . ?
C6 H6 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.363(3) . ?
C23 H23 0.9500 . ?
C16 C19 1.385(4) . ?
C16 H16 0.9500 . ?
C24 C25 1.464(3) . ?
C9 C11 1.386(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C19 C20 1.508(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C11 H11 0.9500 . ?
C25 C26 1.373(4) . ?
C25 C30 1.377(4) . ?
C5 C4 1.356(5) . ?
C5 H5 0.9500 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C30 C29 1.389(5) . ?
C30 H30 0.9500 . ?
C28 C29 1.346(5) . ?
C28 C27 1.363(5) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C26 C27 1.371(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
O1 P1 C7 114.57(9) . . ?
O1 P1 C1 111.52(9) . . ?
C7 P1 C1 105.58(9) . . ?
O1 P1 C13 112.68(9) . . ?
C7 P1 C13 105.83(8) . . ?
C1 P1 C13 106.01(9) . . ?
C21 C13 C14 121.90(18) . . ?
C21 C13 P1 120.64(16) . . ?
C14 C13 P1 117.46(14) . . ?
C23 N1 N2 111.0(2) . . ?
C23 N1 C22 128.52(19) . . ?
N2 N1 C22 120.28(19) . . ?
C18 C14 C15 118.23(19) . . ?
C18 C14 C13 122.37(18) . . ?
C15 C14 C13 119.38(18) . . ?
C13 C21 C22 128.11(19) . . ?
C13 C21 I1 118.73(15) . . ?
C22 C21 I1 113.11(14) . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C18 C14 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C14 C18 H18 119.6 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 P1 123.19(16) . . ?
C6 C1 P1 116.92(17) . . ?
C9 C7 C8 119.35(19) . . ?
C9 C7 P1 118.90(15) . . ?
C8 C7 P1 121.63(16) . . ?
N2 N3 C24 109.1(2) . . ?
N3 N2 N1 106.9(2) . . ?
C7 C8 C10 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C10 C8 H8 120.2 . . ?
C10 C12 C11 120.5(2) . . ?
C10 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C18 C17 C19 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C19 C17 H17 119.5 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C22 C21 113.02(18) . . ?
N1 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
N1 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N1 C23 C24 105.4(2) . . ?
N1 C23 H23 127.3 . . ?
C24 C23 H23 127.3 . . ?
C15 C16 C19 121.1(2) . . ?
C15 C16 H16 119.4 . . ?
C19 C16 H16 119.4 . . ?
C23 C24 N3 107.7(2) . . ?
C23 C24 C25 130.5(2) . . ?
N3 C24 C25 121.8(2) . . ?
C7 C9 C11 120.7(2) . . ?
C7 C9 H9 119.6 . . ?
C11 C9 H9 119.6 . . ?
C12 C10 C8 120.4(2) . . ?
C12 C10 H10 119.8 . . ?
C8 C10 H10 119.8 . . ?
C16 C19 C17 118.2(2) . . ?
C16 C19 C20 121.5(3) . . ?
C17 C19 C20 120.2(3) . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C12 C11 C9 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C9 C11 H11 120.3 . . ?
C26 C25 C30 118.1(3) . . ?
C26 C25 C24 121.4(3) . . ?
C30 C25 C24 120.5(3) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
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 . . ?
C25 C30 C29 120.1(3) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C28 C27 119.1(3) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C28 C29 C30 121.0(3) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 120.8(4) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.149
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound28
_database_code_depnum_ccdc_archive 'CCDC 1905984'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl F I O P'
_chemical_formula_weight         496.66

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2639(11)
_cell_length_b                   8.5040(13)
_cell_length_c                   29.114(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.974(5)
_cell_angle_gamma                90.00
_cell_volume                     2030.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3944
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      23.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16352
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4277
_reflns_number_gt                2915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0334P)²+4.5655P] where P=(Fo²+2Fc²)/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         4277
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C21 C 0.5711(6) 0.9232(7) 0.15900(19) 0.0527(14) Uani 1 1 d . . .
H21 H 0.5838 1.0224 0.1724 0.063 Uiso 1 1 calc R . .
I1 I 0.33767(4) 1.12111(5) 0.056152(13) 0.05227(14) Uani 1 1 d . . .
P1 P 0.90764(14) 1.03247(15) 0.09443(4) 0.0337(3) Uani 1 1 d . . .
O1 O 0.9750(4) 1.1260(4) 0.05784(11) 0.0452(8) Uani 1 1 d . . .
Cl1 Cl 0.4219(3) 0.4994(3) 0.19541(9) 0.1372(11) Uani 1 1 d . . .
C14 C 0.5957(5) 1.1315(6) 0.06268(16) 0.0399(11) Uani 1 1 d . . .
C13 C 0.6844(5) 1.0268(5) 0.08876(15) 0.0335(10) Uani 1 1 d . . .
C16 C 0.6123(5) 0.8979(6) 0.11474(17) 0.0391(11) Uani 1 1 d . . .
C1 C 0.9675(6) 1.1108(6) 0.15182(16) 0.0431(12) Uani 1 1 d . . .
C7 C 0.9748(5) 0.8308(5) 0.09509(16) 0.0352(11) Uani 1 1 d . . .
F1 F 0.5687(7) 1.3874(6) 0.0333(2) 0.149(2) Uani 1 1 d . . .
C15 C 0.6571(7) 1.2610(7) 0.0342(2) 0.0570(15) Uani 1 1 d . . .
H15A H 0.7681 1.2868 0.0467 0.068 Uiso 1 1 calc R . .
H15B H 0.6590 1.2237 0.0028 0.068 Uiso 1 1 calc R . .
C12 C 1.0211(6) 0.7704(7) 0.05444(18) 0.0498(14) Uani 1 1 d . . .
H12 H 1.0173 0.8333 0.0282 0.060 Uiso 1 1 calc R . .
C2 C 0.8694(8) 1.2141(7) 0.1726(2) 0.0642(17) Uani 1 1 d . . .
H2 H 0.7657 1.2387 0.1583 0.077 Uiso 1 1 calc R . .
C19 C 0.4925(8) 0.6550(9) 0.1633(3) 0.076(2) Uani 1 1 d . . .
C20 C 0.5101(7) 0.7982(10) 0.1834(2) 0.0704(19) Uani 1 1 d . . .
H20 H 0.4822 0.8139 0.2131 0.084 Uiso 1 1 calc R . .
C18 C 0.5271(8) 0.6275(8) 0.1197(3) 0.079(2) Uani 1 1 d . . .
H18 H 0.5099 0.5289 0.1062 0.095 Uiso 1 1 calc R . .
C5 C 1.1801(10) 1.1514(9) 0.2141(2) 0.083(2) Uani 1 1 d . . .
H5 H 1.2856 1.1314 0.2279 0.099 Uiso 1 1 calc R . .
C17 C 0.5889(7) 0.7504(7) 0.0958(2) 0.0568(15) Uani 1 1 d . . .
H17 H 0.6153 0.7325 0.0661 0.068 Uiso 1 1 calc R . .
C11 C 1.0727(8) 0.6165(8) 0.0531(3) 0.0748(19) Uani 1 1 d . . .
H11 H 1.1051 0.5763 0.0260 0.090 Uiso 1 1 calc R . .
C6 C 1.1245(7) 1.0806(7) 0.17314(19) 0.0597(16) Uani 1 1 d . . .
H6 H 1.1918 1.0120 0.1594 0.072 Uiso 1 1 calc R . .
C4 C 1.0826(13) 1.2506(11) 0.2349(2) 0.100(3) Uani 1 1 d . . .
H4 H 1.1221 1.2981 0.2628 0.120 Uiso 1 1 calc R . .
C9 C 1.0332(8) 0.5807(8) 0.1310(3) 0.075(2) Uani 1 1 d . . .
H9 H 1.0377 0.5163 0.1569 0.090 Uiso 1 1 calc R . .
C10 C 1.0769(8) 0.5228(8) 0.0911(3) 0.084(2) Uani 1 1 d . . .
H10 H 1.1100 0.4185 0.0896 0.101 Uiso 1 1 calc R . .
C8 C 0.9818(7) 0.7349(7) 0.1337(2) 0.0571(15) Uani 1 1 d . . .
H8 H 0.9521 0.7740 0.1613 0.069 Uiso 1 1 calc R . .
C3 C 0.9268(12) 1.2812(9) 0.2152(3) 0.094(3) Uani 1 1 d . . .
H3 H 0.8596 1.3465 0.2302 0.112 Uiso 1 1 calc R . .


_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
C21 C16 1.389(7) . ?
C21 C20 1.406(8) . ?
I1 C14 2.120(4) . ?
P1 O1 1.490(3) . ?
P1 C7 1.802(5) . ?
P1 C1 1.811(5) . ?
P1 C13 1.832(5) . ?
Cl1 C19 1.759(6) . ?
C14 C13 1.331(6) . ?
C14 C15 1.503(7) . ?
C13 C16 1.496(6) . ?
C16 C17 1.374(7) . ?
C1 C2 1.384(8) . ?
C1 C6 1.392(7) . ?
C7 C8 1.384(7) . ?
C7 C12 1.386(7) . ?
F1 C15 1.298(6) . ?
C12 C11 1.379(8) . ?
C2 C3 1.395(9) . ?
C19 C20 1.351(10) . ?
C19 C18 1.355(10) . ?
C18 C17 1.387(8) . ?
C5 C4 1.358(11) . ?
C5 C6 1.366(9) . ?
C11 C10 1.360(10) . ?
C4 C3 1.369(11) . ?
C9 C10 1.350(10) . ?
C9 C8 1.384(9) . ?

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
C16 C21 C20 119.7(6) . . ?
O1 P1 C7 112.0(2) . . ?
O1 P1 C1 112.3(2) . . ?
C7 P1 C1 106.9(2) . . ?
O1 P1 C13 114.1(2) . . ?
C7 P1 C13 106.3(2) . . ?
C1 P1 C13 104.6(2) . . ?
C13 C14 C15 127.3(4) . . ?
C13 C14 I1 120.1(4) . . ?
C15 C14 I1 112.6(3) . . ?
C14 C13 C16 123.6(4) . . ?
C14 C13 P1 120.8(4) . . ?
C16 C13 P1 115.6(3) . . ?
C17 C16 C21 118.4(5) . . ?
C17 C16 C13 120.7(5) . . ?
C21 C16 C13 120.8(5) . . ?
C2 C1 C6 119.0(5) . . ?
C2 C1 P1 121.9(4) . . ?
C6 C1 P1 118.6(4) . . ?
C8 C7 C12 119.1(5) . . ?
C8 C7 P1 123.5(4) . . ?
C12 C7 P1 117.4(4) . . ?
F1 C15 C14 113.1(5) . . ?
C11 C12 C7 119.6(6) . . ?
C1 C2 C3 119.7(7) . . ?
C20 C19 C18 122.5(6) . . ?
C20 C19 Cl1 118.2(6) . . ?
C18 C19 Cl1 119.3(6) . . ?
C19 C20 C21 119.2(6) . . ?
C19 C18 C17 118.3(7) . . ?
C4 C5 C6 120.5(7) . . ?
C16 C17 C18 121.8(6) . . ?
C10 C11 C12 120.7(6) . . ?
C5 C6 C1 120.3(7) . . ?
C5 C4 C3 120.6(7) . . ?
C10 C9 C8 120.7(6) . . ?
C9 C10 C11 120.1(6) . . ?
C7 C8 C9 119.6(6) . . ?
C4 C3 C2 119.7(7) . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.088
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound27
_database_code_depnum_ccdc_archive 'CCDC 1905983'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 F I O2 P'
_chemical_formula_weight         492.24

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   8.2948(19)
_cell_length_b                   26.144(6)
_cell_length_c                   14.533(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.408(4)
_cell_angle_gamma                90.00
_cell_volume                     3142.3(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7851
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.68

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29977
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             11020
_reflns_number_gt                7724
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1136P)²+0.0000P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         11020
_refine_ls_number_parameters     733
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1700
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I3 I 0.73312(7) 0.28483(3) 0.90586(6) 0.0644(2) Uani 1 1 d . . .
P3 P 0.1727(3) 0.31891(11) 0.82960(19) 0.0499(6) Uani 1 1 d . . .
O5 O 0.0948(10) 0.2916(3) 0.9050(5) 0.0583(19) Uani 1 1 d . . .
C58 C 0.4764(13) 0.2840(4) 0.8942(8) 0.050(3) Uani 1 1 d . . .
C61 C 0.5122(14) 0.3419(5) 0.6912(9) 0.066(3) Uani 1 1 d . . .
H61 H 0.4897 0.3094 0.6674 0.079 Uiso 1 1 calc R . .
C60 C 0.4747(11) 0.3543(4) 0.7797(8) 0.050(2) Uani 1 1 d . . .
C57 C 0.3947(12) 0.3164(4) 0.8403(7) 0.051(2) Uani 1 1 d . . .
C59 C 0.4090(14) 0.2444(5) 0.9590(9) 0.067(3) Uani 1 1 d . . .
H59A H 0.4127 0.2584 1.0209 0.081 Uiso 1 1 calc R . .
H59B H 0.2967 0.2376 0.9391 0.081 Uiso 1 1 calc R . .
C65 C 0.6124(15) 0.4254(5) 0.6693(10) 0.071(3) Uani 1 1 d . . .
C64 C 0.5817(15) 0.4387(5) 0.7569(10) 0.071(3) Uani 1 1 d . . .
H64 H 0.6073 0.4713 0.7790 0.085 Uiso 1 1 calc R . .
C63 C 0.5112(14) 0.4029(5) 0.8138(9) 0.066(3) Uani 1 1 d . . .
H63 H 0.4892 0.4117 0.8736 0.079 Uiso 1 1 calc R . .
C62 C 0.5823(18) 0.3777(5) 0.6397(10) 0.075(4) Uani 1 1 d . . .
H62 H 0.6105 0.3687 0.5811 0.090 Uiso 1 1 calc R . .
I2 I 1.18032(8) 1.04165(4) 0.43761(6) 0.0817(3) Uani 1 1 d . . .
P2 P 0.6191(3) 1.01137(11) 0.36253(19) 0.0480(6) Uani 1 1 d . . .
O3 O 0.5430(10) 1.0369(3) 0.4401(5) 0.063(2) Uani 1 1 d . . .
C36 C 0.9254(12) 1.0435(4) 0.4286(8) 0.053(3) Uani 1 1 d . . .
C38 C 0.9206(12) 0.9746(4) 0.3103(7) 0.050(2) Uani 1 1 d . . .
C35 C 0.8394(11) 1.0127(4) 0.3703(7) 0.052(3) Uani 1 1 d . . .
C37 C 0.8637(14) 1.0815(5) 0.4969(8) 0.061(3) Uani 1 1 d . . .
H37A H 0.7466 1.0830 0.4888 0.074 Uiso 1 1 calc R . .
H37B H 0.8939 1.0700 0.5593 0.074 Uiso 1 1 calc R . .
C43 C 0.9345(14) 0.9838(5) 0.2175(8) 0.064(3) Uani 1 1 d . . .
H43 H 0.8983 1.0147 0.1918 0.077 Uiso 1 1 calc R . .
I1 I -0.09768(8) 0.62953(3) 0.62345(6) 0.0690(2) Uani 1 1 d . . .
P1 P 0.4654(3) 0.65563(11) 0.70253(19) 0.0511(6) Uani 1 1 d . . .
O1 O 0.5360(11) 0.6304(3) 0.6247(6) 0.062(2) Uani 1 1 d . . .
C14 C 0.1587(15) 0.6256(4) 0.6325(8) 0.053(3) Uani 1 1 d . . .
C16 C 0.1686(12) 0.6895(4) 0.7583(7) 0.050(2) Uani 1 1 d . . .
C13 C 0.2439(12) 0.6547(4) 0.6951(7) 0.050(2) Uani 1 1 d . . .
O2 O -0.0410(13) 0.7874(4) 0.9416(7) 0.084(3) Uani 1 1 d . . .
C2 C 0.5809(16) 0.7445(5) 0.6336(8) 0.066(3) Uani 1 1 d . . .
H2 H 0.5948 0.7251 0.5812 0.080 Uiso 1 1 calc R . .
C1 C 0.5192(13) 0.7219(4) 0.7109(8) 0.053(3) Uani 1 1 d . . .
C15 C 0.2211(13) 0.5905(5) 0.5636(8) 0.062(3) Uani 1 1 d . . .
H15A H 0.2115 0.6068 0.5035 0.074 Uiso 1 1 calc R . .
H15B H 0.3349 0.5839 0.5798 0.074 Uiso 1 1 calc R . .
C21 C 0.1325(14) 0.6743(5) 0.8459(8) 0.061(3) Uani 1 1 d . . .
H21 H 0.1568 0.6412 0.8655 0.073 Uiso 1 1 calc R . .
C19 C 0.0233(14) 0.7577(5) 0.8774(8) 0.059(3) Uani 1 1 d . . .
C4 C 0.6210(18) 0.7958(6) 0.6357(11) 0.083(4) Uani 1 1 d . . .
H4 H 0.6594 0.8109 0.5837 0.099 Uiso 1 1 calc R . .
C17 C 0.1241(15) 0.7386(5) 0.7323(8) 0.066(3) Uani 1 1 d . . .
H17 H 0.1416 0.7494 0.6729 0.079 Uiso 1 1 calc R . .
C18 C 0.0543(16) 0.7726(5) 0.7911(10) 0.070(3) Uani 1 1 d . . .
H18 H 0.0288 0.8057 0.7713 0.084 Uiso 1 1 calc R . .
C20 C 0.0602(15) 0.7080(5) 0.9055(8) 0.065(3) Uani 1 1 d . . .
H20 H 0.0369 0.6971 0.9639 0.078 Uiso 1 1 calc R . .
C6 C 0.605(2) 0.8252(6) 0.7142(11) 0.086(4) Uani 1 1 d . . .
H6 H 0.6339 0.8595 0.7149 0.103 Uiso 1 1 calc R . .
C5 C 0.5479(19) 0.8039(6) 0.7883(11) 0.090(4) Uani 1 1 d . . .
H5 H 0.5347 0.8237 0.8403 0.107 Uiso 1 1 calc R . .
C3 C 0.5075(17) 0.7515(5) 0.7885(9) 0.076(4) Uani 1 1 d . . .
H3 H 0.4725 0.7368 0.8416 0.092 Uiso 1 1 calc R . .
F1 F 0.1396(13) 0.5455(3) 0.5591(8) 0.120(4) Uani 1 1 d . . .
O6 O 0.6780(15) 0.4588(4) 0.6063(9) 0.111(4) Uani 1 1 d . . .
F3 F 0.4906(14) 0.2013(4) 0.9605(9) 0.134(4) Uani 1 1 d . . .
F2 F 0.9233(17) 1.1272(4) 0.4851(11) 0.150(5) Uani 1 1 d . . .
C7 C 0.5227(15) 0.6246(5) 0.8110(9) 0.064(3) Uani 1 1 d . . .
O4 O 1.1133(14) 0.8682(4) 0.1390(7) 0.088(3) Uani 1 1 d . . .
C45 C 0.1159(13) 0.2923(5) 0.7174(8) 0.059(3) Uani 1 1 d . . .
C29 C 0.5553(14) 1.0408(4) 0.2528(8) 0.057(3) Uani 1 1 d . . .
C9 C 0.708(3) 0.6140(7) 0.9405(13) 0.110(6) Uani 1 1 d . . .
H9 H 0.7988 0.6256 0.9755 0.132 Uiso 1 1 calc R . .
C8 C 0.654(2) 0.6400(7) 0.8641(11) 0.097(5) Uani 1 1 d . . .
H8 H 0.7091 0.6693 0.8477 0.117 Uiso 1 1 calc R . .
C55 C 0.0202(18) 0.4582(6) 0.9064(10) 0.079(4) Uani 1 1 d . . .
H55 H -0.0152 0.4721 0.9602 0.095 Uiso 1 1 calc R . .
C51 C 0.1173(12) 0.3856(5) 0.8250(8) 0.058(3) Uani 1 1 d . . .
C49 C -0.068(3) 0.2890(8) 0.5881(12) 0.109(6) Uani 1 1 d . . .
H49 H -0.1594 0.3020 0.5547 0.130 Uiso 1 1 calc R . .
C41 C 1.0516(14) 0.9010(5) 0.2001(8) 0.062(3) Uani 1 1 d . . .
C53 C 0.0978(17) 0.4676(6) 0.7526(11) 0.084(4) Uani 1 1 d . . .
H53 H 0.1131 0.4886 0.7023 0.101 Uiso 1 1 calc R . .
C56 C 0.0579(13) 0.4069(5) 0.9016(9) 0.064(3) Uani 1 1 d . . .
H56 H 0.0425 0.3861 0.9520 0.076 Uiso 1 1 calc R . .
C34 C 0.6351(18) 1.0829(5) 0.2211(9) 0.076(4) Uani 1 1 d . . .
H34 H 0.7312 1.0945 0.2511 0.091 Uiso 1 1 calc R . .
C40 C 1.0409(15) 0.8916(5) 0.2920(8) 0.067(3) Uani 1 1 d . . .
H40 H 1.0779 0.8608 0.3178 0.081 Uiso 1 1 calc R . .
C50 C -0.0206(19) 0.3099(7) 0.6665(11) 0.097(5) Uani 1 1 d . . .
H50 H -0.0789 0.3370 0.6886 0.116 Uiso 1 1 calc R . .
C39 C 0.9734(14) 0.9289(5) 0.3473(8) 0.067(3) Uani 1 1 d . . .
H39 H 0.9644 0.9224 0.4096 0.080 Uiso 1 1 calc R . .
C33 C 0.565(3) 1.1076(6) 0.1413(13) 0.117(7) Uani 1 1 d . . .
H33 H 0.6179 1.1355 0.1175 0.140 Uiso 1 1 calc R . .
C12 C 0.4433(18) 0.5821(5) 0.8357(10) 0.079(4) Uani 1 1 d . . .
H12 H 0.3516 0.5714 0.8001 0.095 Uiso 1 1 calc R . .
C30 C 0.4067(16) 1.0253(6) 0.2067(9) 0.080(4) Uani 1 1 d . . .
H30 H 0.3462 0.9985 0.2282 0.096 Uiso 1 1 calc R . .
C52 C 0.1364(15) 0.4171(5) 0.7486(9) 0.070(3) Uani 1 1 d . . .
H52 H 0.1753 0.4035 0.6955 0.084 Uiso 1 1 calc R . .
C42 C 1.0007(16) 0.9480(5) 0.1628(9) 0.070(3) Uani 1 1 d . . .
H42 H 1.0118 0.9551 0.1009 0.084 Uiso 1 1 calc R . .
C23 C 0.5659(13) 0.9449(5) 0.3544(10) 0.068(3) Uani 1 1 d . . .
C44 C 1.152(2) 0.8180(6) 0.1671(12) 0.097(5) Uani 1 1 d . . .
H44A H 1.0562 0.8012 0.1853 0.145 Uiso 1 1 calc R . .
H44B H 1.2319 0.8188 0.2184 0.145 Uiso 1 1 calc R . .
H44C H 1.1933 0.7996 0.1168 0.145 Uiso 1 1 calc R . .
C66 C 0.708(2) 0.5061(7) 0.6282(14) 0.129(8) Uani 1 1 d . . .
H66A H 0.7155 0.5096 0.6942 0.193 Uiso 1 1 calc R . .
H66B H 0.6220 0.5274 0.6019 0.193 Uiso 1 1 calc R . .
H66C H 0.8081 0.5163 0.6049 0.193 Uiso 1 1 calc R . .
C11 C 0.496(2) 0.5545(7) 0.9130(13) 0.108(5) Uani 1 1 d . . .
H11 H 0.4420 0.5249 0.9282 0.130 Uiso 1 1 calc R . .
C54 C 0.0360(19) 0.4883(6) 0.8304(13) 0.091(4) Uani 1 1 d . . .
H54 H 0.0053 0.5225 0.8310 0.109 Uiso 1 1 calc R . .
C46 C 0.2003(17) 0.2533(6) 0.6827(11) 0.083(4) Uani 1 1 d . . .
H46 H 0.2944 0.2418 0.7150 0.100 Uiso 1 1 calc R . .
C10 C 0.630(3) 0.5704(7) 0.9679(12) 0.114(6) Uani 1 1 d . . .
H10 H 0.6659 0.5527 1.0210 0.136 Uiso 1 1 calc R . .
C32 C 0.422(3) 1.0912(9) 0.0982(13) 0.119(8) Uani 1 1 d . . .
H32 H 0.3728 1.1085 0.0476 0.143 Uiso 1 1 calc R . .
C28 C 0.5004(17) 0.9242(7) 0.4318(13) 0.111(7) Uani 1 1 d . . .
H28 H 0.4818 0.9442 0.4828 0.133 Uiso 1 1 calc R . .
C22 C -0.053(2) 0.8407(6) 0.9231(12) 0.099(5) Uani 1 1 d . . .
H22A H -0.1322 0.8465 0.8725 0.149 Uiso 1 1 calc R . .
H22B H 0.0499 0.8535 0.9076 0.149 Uiso 1 1 calc R . .
H22C H -0.0851 0.8582 0.9769 0.149 Uiso 1 1 calc R . .
C47 C 0.149(3) 0.2304(8) 0.6000(12) 0.109(6) Uani 1 1 d . . .
H47 H 0.2077 0.2035 0.5776 0.131 Uiso 1 1 calc R . .
C24 C 0.5893(18) 0.9151(6) 0.2759(15) 0.102(6) Uani 1 1 d . . .
H24 H 0.6275 0.9294 0.2232 0.122 Uiso 1 1 calc R . .
C48 C 0.014(3) 0.2467(8) 0.5518(10) 0.125(8) Uani 1 1 d . . .
H48 H -0.0238 0.2310 0.4969 0.150 Uiso 1 1 calc R . .
C31 C 0.358(2) 1.0516(7) 0.1302(11) 0.090(5) Uani 1 1 d . . .
H31 H 0.2666 1.0392 0.0965 0.108 Uiso 1 1 calc R . .
C25 C 0.552(2) 0.8623(9) 0.281(3) 0.178(15) Uani 1 1 d . . .
H25 H 0.5558 0.8417 0.2287 0.214 Uiso 1 1 calc R . .
C27 C 0.463(3) 0.8705(10) 0.429(2) 0.152(12) Uani 1 1 d . . .
H27 H 0.4043 0.8561 0.4743 0.183 Uiso 1 1 calc R . .
C26 C 0.511(3) 0.8417(7) 0.363(2) 0.139(11) Uani 1 1 d . . .
H26 H 0.5178 0.8065 0.3712 0.167 Uiso 1 1 calc R . .


_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
I3 C58 2.123(11) . ?
P3 O5 1.495(9) . ?
P3 C45 1.802(12) . ?
P3 C51 1.803(13) . ?
P3 C57 1.838(10) . ?
C58 C57 1.307(15) . ?
C58 C59 1.533(16) . ?
C61 C62 1.359(18) . ?
C61 C60 1.385(17) . ?
C60 C63 1.389(17) . ?
C60 C57 1.513(15) . ?
C59 F3 1.315(15) . ?
C65 C62 1.336(19) . ?
C65 C64 1.36(2) . ?
C65 O6 1.404(17) . ?
C64 C63 1.405(19) . ?
I2 C36 2.109(11) . ?
P2 O3 1.492(8) . ?
P2 C23 1.795(13) . ?
P2 C29 1.813(12) . ?
P2 C35 1.822(10) . ?
C36 C35 1.335(15) . ?
C36 C37 1.520(17) . ?
C38 C39 1.369(16) . ?
C38 C43 1.384(15) . ?
C38 C35 1.514(15) . ?
C37 F2 1.310(15) . ?
C43 C42 1.369(18) . ?
I1 C14 2.123(12) . ?
P1 O1 1.470(9) . ?
P1 C1 1.791(12) . ?
P1 C7 1.804(13) . ?
P1 C13 1.833(10) . ?
C14 C13 1.344(15) . ?
C14 C15 1.480(16) . ?
C16 C17 1.381(17) . ?
C16 C21 1.387(16) . ?
C16 C13 1.466(15) . ?
O2 C19 1.354(15) . ?
O2 C22 1.423(18) . ?
C2 C4 1.38(2) . ?
C2 C1 1.401(17) . ?
C1 C3 1.376(18) . ?
C15 F1 1.357(14) . ?
C21 C20 1.402(17) . ?
C19 C18 1.356(18) . ?
C19 C20 1.389(17) . ?
C4 C6 1.39(2) . ?
C17 C18 1.391(18) . ?
C6 C5 1.33(2) . ?
C5 C3 1.41(2) . ?
O6 C66 1.295(19) . ?
C7 C8 1.35(2) . ?
C7 C12 1.353(18) . ?
O4 C41 1.362(14) . ?
O4 C44 1.404(18) . ?
C45 C46 1.355(19) . ?
C45 C50 1.383(19) . ?
C29 C34 1.380(19) . ?
C29 C30 1.417(18) . ?
C9 C8 1.35(2) . ?
C9 C10 1.38(3) . ?
C55 C54 1.37(2) . ?
C55 C56 1.379(19) . ?
C51 C56 1.370(17) . ?
C51 C52 1.400(17) . ?
C49 C50 1.30(2) . ?
C49 C48 1.42(3) . ?
C41 C40 1.368(17) . ?
C41 C42 1.396(18) . ?
C53 C52 1.36(2) . ?
C53 C54 1.39(2) . ?
C34 C33 1.41(2) . ?
C40 C39 1.406(18) . ?
C33 C32 1.37(3) . ?
C12 C11 1.38(2) . ?
C30 C31 1.34(2) . ?
C23 C28 1.39(2) . ?
C23 C24 1.41(2) . ?
C11 C10 1.38(3) . ?
C46 C47 1.38(2) . ?
C32 C31 1.27(3) . ?
C28 C27 1.44(3) . ?
C47 C48 1.34(3) . ?
C24 C25 1.42(3) . ?
C25 C26 1.37(4) . ?
C27 C26 1.31(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
O5 P3 C45 112.4(5) . . ?
O5 P3 C51 111.4(5) . . ?
C45 P3 C51 106.9(6) . . ?
O5 P3 C57 114.0(5) . . ?
C45 P3 C57 104.6(5) . . ?
C51 P3 C57 106.8(5) . . ?
C57 C58 C59 127.4(10) . . ?
C57 C58 I3 120.8(8) . . ?
C59 C58 I3 111.7(7) . . ?
C62 C61 C60 119.1(13) . . ?
C63 C60 C61 119.2(11) . . ?
C63 C60 C57 119.1(10) . . ?
C61 C60 C57 121.7(10) . . ?
C58 C57 C60 122.9(9) . . ?
C58 C57 P3 123.0(8) . . ?
C60 C57 P3 114.1(7) . . ?
F3 C59 C58 112.1(10) . . ?
C62 C65 C64 119.7(13) . . ?
C62 C65 O6 116.3(14) . . ?
C64 C65 O6 124.1(13) . . ?
C65 C64 C63 119.7(13) . . ?
C60 C63 C64 119.3(12) . . ?
C65 C62 C61 123.0(14) . . ?
O3 P2 C23 111.5(6) . . ?
O3 P2 C29 111.3(5) . . ?
C23 P2 C29 107.5(6) . . ?
O3 P2 C35 115.2(5) . . ?
C23 P2 C35 105.2(5) . . ?
C29 P2 C35 105.7(5) . . ?
C35 C36 C37 128.2(9) . . ?
C35 C36 I2 120.7(8) . . ?
C37 C36 I2 111.1(7) . . ?
C39 C38 C43 119.0(10) . . ?
C39 C38 C35 119.4(9) . . ?
C43 C38 C35 121.5(10) . . ?
C36 C35 C38 121.4(9) . . ?
C36 C35 P2 122.4(8) . . ?
C38 C35 P2 116.1(7) . . ?
F2 C37 C36 111.2(10) . . ?
C42 C43 C38 121.0(12) . . ?
O1 P1 C1 112.0(5) . . ?
O1 P1 C7 112.1(6) . . ?
C1 P1 C7 109.2(6) . . ?
O1 P1 C13 113.9(5) . . ?
C1 P1 C13 105.1(5) . . ?
C7 P1 C13 104.0(5) . . ?
C13 C14 C15 128.0(11) . . ?
C13 C14 I1 119.1(8) . . ?
C15 C14 I1 112.9(8) . . ?
C17 C16 C21 116.4(10) . . ?
C17 C16 C13 121.4(10) . . ?
C21 C16 C13 122.1(10) . . ?
C14 C13 C16 123.3(10) . . ?
C14 C13 P1 121.3(8) . . ?
C16 C13 P1 115.4(8) . . ?
C19 O2 C22 117.3(11) . . ?
C4 C2 C1 119.6(12) . . ?
C3 C1 C2 118.2(11) . . ?
C3 C1 P1 124.6(9) . . ?
C2 C1 P1 117.2(9) . . ?
F1 C15 C14 111.8(10) . . ?
C16 C21 C20 121.4(12) . . ?
O2 C19 C18 125.7(12) . . ?
O2 C19 C20 115.0(11) . . ?
C18 C19 C20 119.3(11) . . ?
C2 C4 C6 121.1(13) . . ?
C16 C17 C18 122.7(11) . . ?
C19 C18 C17 120.1(12) . . ?
C19 C20 C21 120.0(11) . . ?
C5 C6 C4 119.7(14) . . ?
C6 C5 C3 120.5(14) . . ?
C1 C3 C5 120.9(12) . . ?
C66 O6 C65 120.6(16) . . ?
C8 C7 C12 118.8(13) . . ?
C8 C7 P1 120.8(11) . . ?
C12 C7 P1 120.0(11) . . ?
C41 O4 C44 119.2(11) . . ?
C46 C45 C50 118.4(13) . . ?
C46 C45 P3 121.4(10) . . ?
C50 C45 P3 120.1(12) . . ?
C34 C29 C30 119.5(12) . . ?
C34 C29 P2 121.2(10) . . ?
C30 C29 P2 118.6(10) . . ?
C8 C9 C10 121.5(18) . . ?
C7 C8 C9 121.4(16) . . ?
C54 C55 C56 118.7(14) . . ?
C56 C51 C52 118.3(12) . . ?
C56 C51 P3 118.0(9) . . ?
C52 C51 P3 123.6(10) . . ?
C50 C49 C48 122.0(17) . . ?
C40 C41 O4 125.4(12) . . ?
C40 C41 C42 119.8(11) . . ?
O4 C41 C42 114.8(11) . . ?
C52 C53 C54 121.0(14) . . ?
C51 C56 C55 122.3(13) . . ?
C29 C34 C33 117.6(16) . . ?
C41 C40 C39 119.5(12) . . ?
C49 C50 C45 120.8(18) . . ?
C38 C39 C40 120.7(11) . . ?
C32 C33 C34 121.2(19) . . ?
C7 C12 C11 121.0(15) . . ?
C31 C30 C29 116.1(16) . . ?
C53 C52 C51 119.7(13) . . ?
C43 C42 C41 119.9(11) . . ?
C28 C23 C24 121.7(15) . . ?
C28 C23 P2 115.6(13) . . ?
C24 C23 P2 122.7(12) . . ?
C12 C11 C10 120.3(17) . . ?
C55 C54 C53 119.8(15) . . ?
C45 C46 C47 121.1(15) . . ?
C9 C10 C11 117.0(15) . . ?
C31 C32 C33 117.4(19) . . ?
C23 C28 C27 117(2) . . ?
C48 C47 C46 120.4(19) . . ?
C23 C24 C25 117(2) . . ?
C47 C48 C49 117.3(15) . . ?
C32 C31 C30 128.0(19) . . ?
C26 C25 C24 120(3) . . ?
C26 C27 C28 120(2) . . ?
C27 C26 C25 121(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.401
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.105
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound29
_database_code_depnum_ccdc_archive 'CCDC 1905985'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 F I O3 P'
_chemical_formula_weight         410.15

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.7231(17)
_cell_length_b                   7.8520(8)
_cell_length_c                   12.4005(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.700(13)
_cell_angle_gamma                90.00
_cell_volume                     1582.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_min      3.5020
_cell_measurement_theta_max      28.2120

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5935
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2789
_reflns_number_gt                2178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0950P)²+1.2001P] where P=(Fo²+2Fc²)/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         2789
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.40599(3) 0.31380(6) -0.05324(4) 0.0579(3) Uani 1 1 d . . .
P1 P 0.16009(10) 0.5014(2) 0.03078(14) 0.0485(5) Uani 1 1 d . . .
C8 C 0.3589(4) 0.5440(9) 0.1981(5) 0.0501(16) Uani 1 1 d . . .
H8 H 0.3442 0.4445 0.2294 0.060 Uiso 1 1 calc R . .
O2 O 0.1476(3) 0.6891(5) -0.0124(4) 0.0516(12) Uani 1 1 d . . .
C6 C 0.2649(4) 0.4613(8) 0.0215(5) 0.0397(13) Uani 1 1 d . . .
O3 O 0.1683(3) 0.5151(6) 0.1582(4) 0.0534(12) Uani 1 1 d . . .
C11 C 0.4034(5) 0.8366(10) 0.1121(8) 0.066(2) Uani 1 1 d . . .
H11 H 0.4191 0.9362 0.0821 0.080 Uiso 1 1 calc R . .
C9 C 0.4142(5) 0.6534(11) 0.2624(7) 0.065(2) Uani 1 1 d . . .
H9 H 0.4376 0.6265 0.3362 0.078 Uiso 1 1 calc R . .
C14 C 0.2284(5) 0.2148(9) -0.1130(7) 0.060(2) Uani 1 1 d . . .
H14A H 0.1721 0.2376 -0.1093 0.072 Uiso 1 1 calc R . .
H14B H 0.2318 0.2278 -0.1895 0.072 Uiso 1 1 calc R . .
C12 C 0.3471(4) 0.7259(9) 0.0445(6) 0.0520(17) Uani 1 1 d . . .
H12 H 0.3250 0.7523 -0.0297 0.062 Uiso 1 1 calc R . .
C13 C 0.2849(4) 0.3417(8) -0.0416(5) 0.0416(14) Uani 1 1 d . . .
O1 O 0.0976(3) 0.3826(8) -0.0267(5) 0.0813(17) Uani 1 1 d . . .
F1 F 0.2485(4) 0.0522(5) -0.0794(5) 0.0999(19) Uani 1 1 d . . .
C7 C 0.3250(4) 0.5784(8) 0.0893(5) 0.0402(14) Uani 1 1 d . . .
C2 C 0.1125(4) 0.8026(9) 0.1533(6) 0.0534(19) Uani 1 1 d . . .
C5 C 0.0915(5) 0.7974(10) 0.0293(6) 0.057(2) Uani 1 1 d . . .
H5A H 0.0358 0.7553 0.0029 0.069 Uiso 1 1 calc R . .
H5B H 0.0936 0.9119 0.0008 0.069 Uiso 1 1 calc R . .
C1 C 0.1109(5) 0.6241(10) 0.1975(6) 0.0590(18) Uani 1 1 d . . .
H1A H 0.1253 0.6266 0.2780 0.071 Uiso 1 1 calc R . .
H1B H 0.0557 0.5780 0.1735 0.071 Uiso 1 1 calc R . .
C10 C 0.4348(5) 0.8005(10) 0.2190(7) 0.062(2) Uani 1 1 d . . .
H10 H 0.4708 0.8763 0.2635 0.075 Uiso 1 1 calc R . .
C4 C 0.1944(5) 0.8886(12) 0.1986(7) 0.075(2) Uani 1 1 d . . .
H4A H 0.2092 0.8781 0.2780 0.113 Uiso 1 1 calc R . .
H4B H 0.1903 1.0069 0.1786 0.113 Uiso 1 1 calc R . .
H4C H 0.2358 0.8354 0.1680 0.113 Uiso 1 1 calc R . .
C3 C 0.0434(5) 0.9038(12) 0.1901(7) 0.076(2) Uani 1 1 d . . .
H3A H -0.0094 0.8608 0.1515 0.114 Uiso 1 1 calc R . .
H3B H 0.0474 1.0222 0.1728 0.114 Uiso 1 1 calc R . .
H3C H 0.0496 0.8907 0.2686 0.114 Uiso 1 1 calc R . .


_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
I1 C13 2.075(6) . ?
P1 O1 1.456(6) . ?
P1 O3 1.557(5) . ?
P1 O2 1.566(5) . ?
P1 C6 1.811(6) . ?
C8 C7 1.361(9) . ?
C8 C9 1.372(10) . ?
O2 C5 1.450(8) . ?
C6 C13 1.315(9) . ?
C6 C7 1.471(8) . ?
O3 C1 1.454(8) . ?
C11 C10 1.335(12) . ?
C11 C12 1.404(11) . ?
C9 C10 1.353(12) . ?
C14 F1 1.360(8) . ?
C14 C13 1.508(9) . ?
C12 C7 1.372(9) . ?
C2 C5 1.494(9) . ?
C2 C1 1.507(10) . ?
C2 C4 1.510(10) . ?
C2 C3 1.557(10) . ?

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
O1 P1 O3 114.9(3) . . ?
O1 P1 O2 114.4(4) . . ?
O3 P1 O2 104.7(3) . . ?
O1 P1 C6 116.8(3) . . ?
O3 P1 C6 102.9(3) . . ?
O2 P1 C6 101.2(3) . . ?
C7 C8 C9 121.1(7) . . ?
C5 O2 P1 118.4(4) . . ?
C13 C6 C7 123.4(6) . . ?
C13 C6 P1 123.3(5) . . ?
C7 C6 P1 113.3(4) . . ?
C1 O3 P1 118.3(4) . . ?
C10 C11 C12 120.8(7) . . ?
C10 C9 C8 120.2(7) . . ?
F1 C14 C13 111.5(6) . . ?
C7 C12 C11 119.2(7) . . ?
C6 C13 C14 127.5(6) . . ?
C6 C13 I1 120.5(5) . . ?
C14 C13 I1 112.1(5) . . ?
C8 C7 C12 118.7(6) . . ?
C8 C7 C6 120.7(6) . . ?
C12 C7 C6 120.6(6) . . ?
C5 C2 C1 109.2(6) . . ?
C5 C2 C4 111.5(7) . . ?
C1 C2 C4 111.9(6) . . ?
C5 C2 C3 107.7(6) . . ?
C1 C2 C3 106.8(6) . . ?
C4 C2 C3 109.5(6) . . ?
O2 C5 C2 111.6(5) . . ?
O3 C1 C2 110.8(6) . . ?
C11 C10 C9 120.0(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.741
_refine_diff_density_min         -1.253
_refine_diff_density_rms         0.135
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound24
_database_code_depnum_ccdc_archive 'CCDC 1905981'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 I2 O3 P'
_chemical_formula_weight         530.06

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1150(7)
_cell_length_b                   10.3990(10)
_cell_length_c                   19.1186(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.325(4)
_cell_angle_gamma                90.00
_cell_volume                     1810.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    3.568
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25311
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3140
_reflns_number_gt                3025
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+127.8305P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0137(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3140
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2603
_refine_ls_wR_factor_gt          0.2600
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.77089(14) 0.65599(14) 0.63493(8) 0.0456(6) Uani 1 1 d . . .
I1 I 0.55772(18) 0.86665(15) 0.74051(9) 0.0556(6) Uani 1 1 d . . .
P1 P 0.2235(5) 0.5275(5) 0.6309(3) 0.0359(12) Uani 1 1 d . . .
O2 O 0.2439(16) 0.4179(14) 0.5760(8) 0.047(4) Uani 1 1 d . . .
O3 O 0.3096(15) 0.4855(13) 0.6993(7) 0.041(3) Uani 1 1 d . . .
O1 O 0.0684(17) 0.5473(18) 0.6402(10) 0.067(5) Uani 1 1 d . . .
C6 C 0.314(2) 0.6670(18) 0.5984(11) 0.039(4) Uani 1 1 d . . .
C7 C 0.444(2) 0.6966(18) 0.6286(10) 0.035(4) Uani 1 1 d . . .
C14 C 0.288(2) 0.875(2) 0.5339(13) 0.048(5) Uani 1 1 d . . .
H14 H 0.3598 0.9094 0.5644 0.058 Uiso 1 1 calc R . .
C9 C 0.247(2) 0.7484(19) 0.5419(10) 0.036(4) Uani 1 1 d . . .
C8 C 0.568(2) 0.730(2) 0.6586(11) 0.043(5) Uani 1 1 d . . .
C3 C 0.426(2) 0.2972(18) 0.6466(9) 0.033(4) Uani 1 1 d . . .
C12 C 0.115(2) 0.902(2) 0.4359(11) 0.047(5) Uani 1 1 d . . .
C13 C 0.226(2) 0.951(2) 0.4820(12) 0.047(5) Uani 1 1 d . . .
H13 H 0.2567 1.0359 0.4773 0.057 Uiso 1 1 calc R . .
C11 C 0.072(2) 0.779(2) 0.4451(12) 0.054(6) Uani 1 1 d . . .
H11 H -0.0037 0.7464 0.4164 0.064 Uiso 1 1 calc R . .
C5 C 0.316(3) 0.198(2) 0.6677(14) 0.056(6) Uani 1 1 d . . .
H5A H 0.3465 0.1615 0.7120 0.084 Uiso 1 1 calc R . .
H5B H 0.3088 0.1315 0.6329 0.084 Uiso 1 1 calc R . .
H5C H 0.2214 0.2381 0.6716 0.084 Uiso 1 1 calc R . .
C10 C 0.1366(19) 0.701(2) 0.4954(11) 0.040(5) Uani 1 1 d . . .
H10 H 0.1069 0.6156 0.4986 0.048 Uiso 1 1 calc R . .
C2 C 0.439(2) 0.405(2) 0.6987(11) 0.045(5) Uani 1 1 d . . .
H2A H 0.4566 0.3691 0.7450 0.054 Uiso 1 1 calc R . .
H2B H 0.5226 0.4578 0.6880 0.054 Uiso 1 1 calc R . .
C1 C 0.385(2) 0.354(2) 0.5760(12) 0.050(5) Uani 1 1 d . . .
H1A H 0.4599 0.4154 0.5635 0.060 Uiso 1 1 calc R . .
H1B H 0.3821 0.2864 0.5411 0.060 Uiso 1 1 calc R . .
C15 C 0.051(3) 0.986(3) 0.3798(15) 0.075(9) Uani 1 1 d . . .
H15A H 0.1177 0.9914 0.3422 0.112 Uiso 1 1 calc R . .
H15B H 0.0349 1.0703 0.3983 0.112 Uiso 1 1 calc R . .
H15C H -0.0405 0.9504 0.3625 0.112 Uiso 1 1 calc R . .
C4 C 0.578(3) 0.236(3) 0.6435(14) 0.070(8) Uani 1 1 d . . .
H4A H 0.6512 0.3024 0.6428 0.105 Uiso 1 1 calc R . .
H4B H 0.5828 0.1847 0.6019 0.105 Uiso 1 1 calc R . .
H4C H 0.5959 0.1827 0.6840 0.105 Uiso 1 1 calc R . .


_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
I2 C8 2.07(2) . ?
I1 C8 2.12(2) . ?
P1 O1 1.447(16) . ?
P1 O3 1.560(14) . ?
P1 O2 1.565(16) . ?
P1 C6 1.79(2) . ?
O2 C1 1.45(3) . ?
O3 C2 1.44(2) . ?
C6 C7 1.33(3) . ?
C6 C9 1.48(3) . ?
C7 C8 1.29(3) . ?
C14 C9 1.38(3) . ?
C14 C13 1.38(3) . ?
C14 H14 0.9300 . ?
C9 C10 1.40(3) . ?
C3 C5 1.50(3) . ?
C3 C1 1.50(3) . ?
C3 C4 1.53(3) . ?
C3 C2 1.50(3) . ?
C12 C11 1.35(3) . ?
C12 C13 1.41(3) . ?
C12 C15 1.48(3) . ?
C13 H13 0.9300 . ?
C11 C10 1.37(3) . ?
C11 H11 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C10 H10 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
O1 P1 O3 113.4(9) . . ?
O1 P1 O2 109.2(11) . . ?
O3 P1 O2 106.8(7) . . ?
O1 P1 C6 113.1(10) . . ?
O3 P1 C6 107.1(9) . . ?
O2 P1 C6 106.8(9) . . ?
C1 O2 P1 117.6(13) . . ?
C2 O3 P1 122.5(12) . . ?
C7 C6 C9 121.0(18) . . ?
C7 C6 P1 116.7(16) . . ?
C9 C6 P1 122.3(14) . . ?
C8 C7 C6 178(2) . . ?
C9 C14 C13 122(2) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C9 C10 117.2(19) . . ?
C14 C9 C6 121.3(18) . . ?
C10 C9 C6 121.5(18) . . ?
C7 C8 I2 125.2(17) . . ?
C7 C8 I1 116.3(16) . . ?
I2 C8 I1 118.5(9) . . ?
C5 C3 C1 111.5(18) . . ?
C5 C3 C4 110.0(19) . . ?
C1 C3 C4 108.6(17) . . ?
C5 C3 C2 111.6(17) . . ?
C1 C3 C2 108.1(16) . . ?
C4 C3 C2 106.8(18) . . ?
C11 C12 C13 118(2) . . ?
C11 C12 C15 123(2) . . ?
C13 C12 C15 119(2) . . ?
C14 C13 C12 120(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C11 C10 122(2) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C10 C9 120.6(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O3 C2 C3 113.4(16) . . ?
O3 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
O3 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O2 C1 C3 111.5(17) . . ?
O2 C1 H1A 109.3 . . ?
C3 C1 H1A 109.3 . . ?
O2 C1 H1B 109.3 . . ?
C3 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.821
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.251
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound17
_database_code_depnum_ccdc_archive 'CCDC 1905979'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl I N3 O P'
_chemical_formula_weight         519.69

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P_21_21_21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   29.548(4)
_cell_length_b                   8.3033(8)
_cell_length_c                   8.5609(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2100.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9352
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      20.35

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42185
_diffrn_reflns_av_R_equivalents  0.2314
_diffrn_reflns_av_sigmaI/netI    0.0947
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3693
_reflns_number_gt                2941
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1069P)²+12.5219P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_number_reflns         3693
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2136
_refine_ls_wR_factor_gt          0.2043
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.57276(3) 1.03413(10) 0.72329(11) 0.0386(3) Uani 1 1 d . . .
P1 P 0.59793(12) 0.4809(4) 0.5950(4) 0.0296(8) Uani 1 1 d . . .
Cl1 Cl 0.70394(18) 1.1122(6) 0.1697(7) 0.0720(15) Uani 1 1 d . . .
O1 O 0.5732(3) 0.3984(11) 0.7231(12) 0.043(2) Uani 1 1 d . . .
C1 C 0.5734(5) 0.4368(14) 0.4054(16) 0.036(3) Uani 1 1 d . . .
C7 C 0.6569(5) 0.4254(15) 0.5959(15) 0.034(3) Uani 1 1 d . . .
C19 C 0.6741(5) 0.9880(15) 0.2952(19) 0.043(4) Uani 1 1 d . . .
N1 N 0.5711(5) 0.7218(17) 0.9957(14) 0.050(3) Uani 1 1 d . . .
C6 C 0.5938(6) 0.3425(17) 0.298(2) 0.048(4) Uani 1 1 d . . .
H6 H 0.6222 0.2989 0.3175 0.057 Uiso 1 1 calc R . .
C16 C 0.6250(4) 0.7904(14) 0.4927(16) 0.027(3) Uani 1 1 d . . .
C20 C 0.6910(5) 0.951(2) 0.437(2) 0.047(4) Uani 1 1 d . . .
H20 H 0.7191 0.9904 0.4670 0.056 Uiso 1 1 calc R . .
C21 C 0.6666(5) 0.8532(19) 0.539(2) 0.047(4) Uani 1 1 d . . .
H21 H 0.6781 0.8299 0.6376 0.056 Uiso 1 1 calc R . .
C18 C 0.6328(5) 0.9252(14) 0.2432(15) 0.037(4) Uani 1 1 d . . .
H18 H 0.6218 0.9496 0.1442 0.045 Uiso 1 1 calc R . .
C15 C 0.5450(5) 0.7065(18) 0.8456(19) 0.039(4) Uani 1 1 d . . .
H15A H 0.5161 0.7607 0.8555 0.047 Uiso 1 1 calc R . .
H15B H 0.5393 0.5937 0.8234 0.047 Uiso 1 1 calc R . .
N2 N 0.6086(6) 0.6569(19) 0.9946(19) 0.057(4) Uani 1 1 d . . .
C13 C 0.5965(4) 0.6997(16) 0.6116(15) 0.025(3) Uani 1 1 d . . .
C4 C 0.5303(7) 0.376(2) 0.126(3) 0.067(6) Uani 1 1 d . . .
H4 H 0.5163 0.3560 0.0310 0.081 Uiso 1 1 calc R . .
C2 C 0.5303(5) 0.4977(16) 0.374(2) 0.048(4) Uani 1 1 d . . .
H2 H 0.5157 0.5594 0.4497 0.058 Uiso 1 1 calc R . .
C3 C 0.5094(6) 0.469(2) 0.237(2) 0.059(4) Uani 1 1 d . . .
H3 H 0.4809 0.5118 0.2175 0.070 Uiso 1 1 calc R . .
C12 C 0.6717(5) 0.3342(17) 0.723(2) 0.042(3) Uani 1 1 d . . .
H12 H 0.6514 0.3056 0.8010 0.050 Uiso 1 1 calc R . .
C8 C 0.6880(5) 0.464(2) 0.4749(18) 0.049(4) Uani 1 1 d . . .
H8 H 0.6786 0.5233 0.3886 0.058 Uiso 1 1 calc R . .
C14 C 0.5720(5) 0.7812(14) 0.7125(16) 0.031(3) Uani 1 1 d . . .
C11 C 0.7161(5) 0.2861(19) 0.734(2) 0.048(4) Uani 1 1 d . . .
H11 H 0.7261 0.2293 0.8206 0.058 Uiso 1 1 calc R . .
C17 C 0.6088(5) 0.8254(16) 0.3431(19) 0.039(3) Uani 1 1 d . . .
H17 H 0.5815 0.7812 0.3102 0.046 Uiso 1 1 calc R . .
C10 C 0.7457(6) 0.323(2) 0.614(3) 0.062(6) Uani 1 1 d . . .
H10 H 0.7754 0.2859 0.6202 0.074 Uiso 1 1 calc R . .
C5 C 0.5722(8) 0.3113(19) 0.158(2) 0.065(5) Uani 1 1 d . . .
H5 H 0.5862 0.2460 0.0838 0.078 Uiso 1 1 calc R . .
N3 N 0.6429(7) 0.602(3) 1.004(3) 0.098(7) Uani 1 1 d . . .
C9 C 0.7327(6) 0.412(2) 0.487(3) 0.066(6) Uani 1 1 d . . .
H9 H 0.7536 0.4371 0.4093 0.079 Uiso 1 1 calc R . .


_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
I1 C14 2.102(12) . ?
P1 O1 1.485(9) . ?
P1 C7 1.802(16) . ?
P1 C1 1.815(15) . ?
P1 C13 1.822(13) . ?
Cl1 C19 1.731(14) . ?
C1 C6 1.35(2) . ?
C1 C2 1.40(2) . ?
C7 C12 1.40(2) . ?
C7 C8 1.42(2) . ?
C19 C20 1.35(2) . ?
C19 C18 1.40(2) . ?
N1 N2 1.23(2) . ?
N1 C15 1.50(2) . ?
C6 C5 1.38(3) . ?
C6 H6 0.9300 . ?
C16 C21 1.39(2) . ?
C16 C17 1.40(2) . ?
C16 C13 1.521(19) . ?
C20 C21 1.39(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C18 C17 1.39(2) . ?
C18 H18 0.9300 . ?
C15 C14 1.523(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N2 N3 1.12(2) . ?
C13 C14 1.315(18) . ?
C4 C3 1.37(3) . ?
C4 C5 1.37(3) . ?
C4 H4 0.9300 . ?
C2 C3 1.35(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C12 C11 1.37(2) . ?
C12 H12 0.9300 . ?
C8 C9 1.40(2) . ?
C8 H8 0.9300 . ?
C11 C10 1.38(3) . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C10 C9 1.37(3) . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C9 H9 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
O1 P1 C7 110.8(6) . . ?
O1 P1 C1 111.7(6) . . ?
C7 P1 C1 109.8(6) . . ?
O1 P1 C13 113.0(6) . . ?
C7 P1 C13 106.1(6) . . ?
C1 P1 C13 105.2(6) . . ?
C6 C1 C2 119.1(15) . . ?
C6 C1 P1 123.3(13) . . ?
C2 C1 P1 117.5(11) . . ?
C12 C7 C8 119.2(15) . . ?
C12 C7 P1 116.5(11) . . ?
C8 C7 P1 124.3(12) . . ?
C20 C19 C18 121.6(13) . . ?
C20 C19 Cl1 120.4(13) . . ?
C18 C19 Cl1 118.0(12) . . ?
N2 N1 C15 114.7(13) . . ?
C1 C6 C5 119.6(16) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C21 C16 C17 119.0(14) . . ?
C21 C16 C13 119.0(13) . . ?
C17 C16 C13 121.7(12) . . ?
C19 C20 C21 120.4(15) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.8(16) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C17 C18 C19 118.2(13) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
N1 C15 C14 109.6(11) . . ?
N1 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N1 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N3 N2 N1 175(2) . . ?
C14 C13 C16 119.3(11) . . ?
C14 C13 P1 125.2(11) . . ?
C16 C13 P1 115.4(9) . . ?
C3 C4 C5 119.4(18) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C3 C2 C1 121.3(16) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.7(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C11 C12 C7 120.6(15) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C9 C8 C7 119.3(16) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C13 C14 C15 124.8(12) . . ?
C13 C14 I1 122.5(10) . . ?
C15 C14 I1 112.3(9) . . ?
C12 C11 C10 119.5(16) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C18 C17 C16 120.9(14) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C9 C10 C11 122.0(17) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C4 C5 C6 120.8(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C10 C9 C8 119.4(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.680
_refine_diff_density_min         -1.471
_refine_diff_density_rms         0.225
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound26
_database_code_depnum_ccdc_archive 'CCDC 1905982'
loop_
_audit_author_name
_audit_author_address
'K C Kumara Swamy'
;University of Hyderabad
India
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 F I O P'
_chemical_formula_weight         476.24

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6921(13)
_cell_length_b                   9.8549(12)
_cell_length_c                   11.1815(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.996(4)
_cell_angle_gamma                90.00
_cell_volume                     1015.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.22

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    1.671
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7310
_exptl_absorpt_correction_T_max  0.8507
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17646
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3554
_reflns_number_gt                3455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.6625P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.8588(5) 0.2448(5) 0.2983(4) 0.0340(9) Uani 1 1 d . . .
I1 I 1.07684(3) 0.36282(4) 0.52861(3) 0.05462(13) Uani 1 1 d . . .
P1 P 0.78832(11) 0.11936(11) 0.17398(10) 0.0284(2) Uani 1 1 d . . .
C14 C 0.9993(5) 0.2410(5) 0.3670(4) 0.0363(9) Uani 1 1 d . . .
O1 O 0.8468(3) -0.0197(3) 0.2124(3) 0.0372(7) Uani 1 1 d . . .
C1 C 0.8295(5) 0.1765(5) 0.0356(4) 0.0335(9) Uani 1 1 d . . .
C15 C 1.1174(6) 0.1512(6) 0.3461(5) 0.0527(13) Uani 1 1 d . . .
H9A H 1.1516 0.0879 0.4154 0.063 Uiso 1 1 calc R . .
H9B H 1.0789 0.0996 0.2691 0.063 Uiso 1 1 calc R . .
C6 C 0.9257(5) 0.2820(5) 0.0360(5) 0.0444(11) Uani 1 1 d . . .
H6 H 0.9650 0.3330 0.1086 0.053 Uiso 1 1 calc R . .
C2 C 0.7722(7) 0.1003(6) -0.0728(5) 0.0551(14) Uani 1 1 d . . .
H2 H 0.7052 0.0319 -0.0757 0.066 Uiso 1 1 calc R . .
C5 C 0.9628(6) 0.3109(6) -0.0708(6) 0.0545(13) Uani 1 1 d . . .
H5 H 1.0243 0.3834 -0.0707 0.065 Uiso 1 1 calc R . .
C4 C 0.9090(7) 0.2327(8) -0.1781(5) 0.0638(17) Uani 1 1 d . . .
H4 H 0.9355 0.2516 -0.2495 0.077 Uiso 1 1 calc R . .
C3 C 0.8177(8) 0.1286(8) -0.1784(5) 0.0693(17) Uani 1 1 d . . .
H3 H 0.7842 0.0747 -0.2498 0.083 Uiso 1 1 calc R . .
F1 F 1.2281(5) 0.2302(6) 0.3383(6) 0.1035(17) Uani 1 1 d . . .
C7 C 0.5936(5) 0.1221(4) 0.1338(4) 0.0317(8) Uani 1 1 d . . .
C11 C 0.3552(6) 0.2178(7) 0.0413(6) 0.0607(15) Uani 1 1 d . . .
H12 H 0.2968 0.2880 -0.0022 0.073 Uiso 1 1 calc R . .
C12 C 0.5079(5) 0.2242(5) 0.0668(5) 0.0453(11) Uani 1 1 d . . .
H11 H 0.5496 0.2973 0.0381 0.054 Uiso 1 1 calc R . .
C8 C 0.5280(6) 0.0113(6) 0.1738(5) 0.0484(12) Uani 1 1 d . . .
H15 H 0.5852 -0.0588 0.2188 0.058 Uiso 1 1 calc R . .
C10 C 0.2949(6) 0.1103(8) 0.0801(7) 0.0625(16) Uani 1 1 d . . .
H13 H 0.1947 0.1063 0.0617 0.075 Uiso 1 1 calc R . .
C9 C 0.3793(7) 0.0058(7) 0.1468(7) 0.0651(16) Uani 1 1 d . . .
H14 H 0.3361 -0.0678 0.1733 0.078 Uiso 1 1 calc R . .
C16 C 0.7556(5) 0.3474(8) 0.3176(5) 0.0645(18) Uani 1 1 d . . .
C21 C 0.6661(8) 0.3351(11) 0.3857(7) 0.085(3) Uani 1 1 d . . .
C17 C 0.7617(10) 0.4858(8) 0.2516(7) 0.083(2) Uani 1 1 d . . .
H17 H 0.8267 0.5012 0.2068 0.100 Uiso 1 1 calc R . .
C18 C 0.6650(14) 0.5840(10) 0.2635(10) 0.122(4) Uani 1 1 d . . .
H21 H 0.6581 0.6672 0.2229 0.147 Uiso 1 1 calc R . .
C20 C 0.5723(10) 0.4431(12) 0.4003(11) 0.108(4) Uani 1 1 d . . .
H19 H 0.5122 0.4334 0.4505 0.129 Uiso 1 1 calc R . .
C19 C 0.5760(12) 0.5524(17) 0.3409(12) 0.119(4) Uani 1 1 d . . .
H22 H 0.5129 0.6205 0.3487 0.143 Uiso 1 1 calc R . .
C22 C 0.6701(9) 0.2127(10) 0.4487(8) 0.086(2) Uani 1 1 d . . .
H25A H 0.6659 0.1388 0.3918 0.129 Uiso 1 1 calc R . .
H25B H 0.5887 0.2077 0.4803 0.129 Uiso 1 1 calc R . .
H25C H 0.7585 0.2073 0.5175 0.129 Uiso 1 1 calc R . .


_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
C13 C14 1.341(7) . ?
C13 C16 1.485(6) . ?
C13 P1 1.827(4) . ?
I1 C14 2.106(4) . ?
P1 O1 1.494(3) . ?
P1 C7 1.800(4) . ?
P1 C1 1.803(4) . ?
C14 C15 1.520(7) . ?
C1 C2 1.388(7) . ?
C1 C6 1.396(7) . ?
C15 F1 1.350(7) . ?
C6 C5 1.379(8) . ?
C2 C3 1.410(8) . ?
C5 C4 1.386(10) . ?
C4 C3 1.354(10) . ?
C7 C12 1.372(7) . ?
C7 C8 1.404(7) . ?
C11 C10 1.345(10) . ?
C11 C12 1.419(7) . ?
C8 C9 1.379(8) . ?
C10 C9 1.382(10) . ?
C16 C21 1.325(10) . ?
C16 C17 1.560(12) . ?
C21 C22 1.391(13) . ?
C21 C20 1.441(11) . ?
C17 C18 1.382(12) . ?
C18 C19 1.433(18) . ?
C20 C19 1.272(17) . ?

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 C13 C16 123.1(4) . . ?
C14 C13 P1 119.4(3) . . ?
C16 C13 P1 117.5(3) . . ?
O1 P1 C7 111.13(19) . . ?
O1 P1 C1 111.60(19) . . ?
C7 P1 C1 105.9(2) . . ?
O1 P1 C13 112.5(2) . . ?
C7 P1 C13 107.24(19) . . ?
C1 P1 C13 108.1(2) . . ?
C13 C14 C15 127.4(4) . . ?
C13 C14 I1 120.4(3) . . ?
C15 C14 I1 112.2(3) . . ?
C2 C1 C6 119.5(4) . . ?
C2 C1 P1 116.5(4) . . ?
C6 C1 P1 123.7(4) . . ?
F1 C15 C14 109.0(5) . . ?
C5 C6 C1 120.2(5) . . ?
C1 C2 C3 118.7(6) . . ?
C6 C5 C4 120.4(5) . . ?
C3 C4 C5 119.6(5) . . ?
C4 C3 C2 121.4(6) . . ?
C12 C7 C8 119.2(4) . . ?
C12 C7 P1 124.0(3) . . ?
C8 C7 P1 116.9(4) . . ?
C10 C11 C12 120.0(6) . . ?
C7 C12 C11 119.7(5) . . ?
C9 C8 C7 120.4(5) . . ?
C11 C10 C9 121.2(5) . . ?
C8 C9 C10 119.5(6) . . ?
C21 C16 C13 127.7(8) . . ?
C21 C16 C17 118.7(7) . . ?
C13 C16 C17 113.6(5) . . ?
C16 C21 C22 116.7(8) . . ?
C16 C21 C20 123.1(11) . . ?
C22 C21 C20 120.2(9) . . ?
C18 C17 C16 116.1(9) . . ?
C17 C18 C19 117.3(10) . . ?
C19 C20 C21 116.4(13) . . ?
C20 C19 C18 128.3(12) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.169
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
