# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_g370_mn_d
_database_code_depnum_ccdc_archive 'CCDC 1842618'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 I N2 P, I'
_chemical_formula_sum            'C5 H9 I2 N2 P'
_chemical_formula_weight         381.91

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.4578(10)
_cell_length_b                   8.6203(7)
_cell_length_c                   9.8671(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.365(3)
_cell_angle_gamma                90
_cell_volume                     1025.62(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1546
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      30.5

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.473
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    6.229
_shelx_estimated_absorpt_T_min   0.216
_shelx_estimated_absorpt_T_max   0.558
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2924
_exptl_absorpt_correction_T_max  0.6678
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12371
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.905
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1666
_reflns_number_gt                1545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
P(H) disordered about the 2-fold axis, s.o.f. = 0.5
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0044P)²+1.5883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.00106(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1666
_refine_ls_number_parameters     60
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0170
_refine_ls_R_factor_gt           0.0142
_refine_ls_wR_factor_ref         0.0282
_refine_ls_wR_factor_gt          0.0274
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.130
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.03797(2) 0.5000 0.73941(2) 0.02005(5) Uani 1 2 d S T P . .
I1 I 0.36650(2) 0.5000 0.53787(2) 0.02566(5) Uani 1 2 d S T P . .
P1 P 0.20451(6) 0.4780(3) 0.61437(8) 0.0193(5) Uani 0.5 1 d D . P A -1
H1 H 0.172(3) 0.349(3) 0.576(5) 0.029 Uiso 0.5 1 d D U P B -1
C1 C 0.30015(17) 0.5000 0.8156(2) 0.0152(4) Uani 1 2 d S T P . .
N1 N 0.33903(11) 0.37479(15) 0.90559(14) 0.0162(2) Uani 1 1 d . . . . .
C2 C 0.40104(13) 0.42151(19) 1.05291(17) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.4370 0.3560 1.1384 0.022 Uiso 1 1 calc R U . . .
C3 C 0.31733(15) 0.21411(19) 0.8532(2) 0.0241(3) Uani 1 1 d . . . . .
H3A H 0.2371 0.1973 0.7984 0.036 Uiso 1 1 calc R U . . .
H3B H 0.3487 0.1440 0.9403 0.036 Uiso 1 1 calc R U . . .
H3C H 0.3516 0.1933 0.7858 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 P1 3.0063(9) . ?
I1 P1 2.6114(9) . ?
P1 C1 1.834(2) . ?
P1 H1 1.195(19) . ?
C1 N1 1.3470(18) 6_565 ?
C1 N1 1.3470(18) . ?
N1 C2 1.3763(19) . ?
N1 C3 1.462(2) . ?
C2 C2 1.353(3) 6_565 ?
C2 H2 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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
C1 P1 I1 91.77(7) . . ?
C1 P1 I2 80.90(7) . . ?
I1 P1 I2 169.83(8) . . ?
C1 P1 H1 115(2) . . ?
I1 P1 H1 102.3(19) . . ?
I2 P1 H1 87.2(19) . . ?
N1 C1 N1 106.50(18) 6_565 . ?
N1 C1 P1 132.58(12) 6_565 . ?
N1 C1 P1 120.74(11) . . ?
C1 N1 C2 109.73(14) . . ?
C1 N1 C3 124.61(13) . . ?
C2 N1 C3 125.66(13) . . ?
C2 C2 N1 107.01(9) 6_565 . ?
C2 C2 H2 126.5 6_565 . ?
N1 C2 H2 126.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 P1 C1 N1 88.6(2) . . . 6_565 ?
I2 P1 C1 N1 -84.3(2) . . . 6_565 ?
I1 P1 C1 N1 -96.90(17) . . . . ?
I2 P1 C1 N1 90.20(17) . . . . ?
N1 C1 N1 C2 1.0(2) 6_565 . . . ?
P1 C1 N1 C2 -174.84(13) . . . . ?
N1 C1 N1 C3 -179.40(11) 6_565 . . . ?
P1 C1 N1 C3 4.8(3) . . . . ?
C1 N1 C2 C2 -0.60(14) . . . 6_565 ?
C3 N1 C2 C2 179.77(13) . . . 6_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
P1 H1 I1 1.195(19) 3.17(2) 4.345(2) 167(3) 7_556
C2 H2 I2 0.95 3.26 4.0721(17) 144.7 7_557
C3 H3B I2 0.98 3.09 4.0503(17) 165.6 7_557
C3 H3C I2 0.98 3.21 4.0552(18) 145.6 3_545

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_g383_mn_i
_database_code_depnum_ccdc_archive 'CCDC 1842621'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H32 I N4 P'
_chemical_formula_sum            'C18 H32 I N4 P'
_chemical_formula_weight         462.34

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.4547(6)
_cell_length_b                   19.5345(12)
_cell_length_c                   11.8695(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.891(3)
_cell_angle_gamma                90
_cell_volume                     2184.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2919
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      30.6

_exptl_crystal_description       prisms
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.691
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.232
_exptl_absorpt_coefficient_mu    1.547
_shelx_estimated_absorpt_T_min   0.415
_shelx_estimated_absorpt_T_max   0.715
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_T_max  0.8293
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12978
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.013
_diffrn_reflns_theta_max         30.607
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3350
_reflns_number_gt                2919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²+2.5501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0036(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0574
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.2500 0.02937(3) 0.5000 0.01728(11) Uani 1 2 d S T P . .
N1 N 0.44564(17) 0.14194(7) 0.51979(13) 0.0292(3) Uani 1 1 d . . . . .
N2 N 0.42296(13) 0.09077(6) 0.67876(10) 0.0185(2) Uani 1 1 d . . . . .
C1 C 0.37440(15) 0.09085(7) 0.56766(13) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.5357(2) 0.17429(9) 0.60114(16) 0.0348(4) Uani 1 1 d . . . . .
H3 H 0.5951 0.2124 0.5896 0.042 Uiso 1 1 calc R U . . .
C4 C 0.52330(18) 0.14159(8) 0.69952(15) 0.0263(3) Uani 1 1 d . . . . .
H4 H 0.5741 0.1516 0.7701 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4410(2) 0.15768(10) 0.39772(17) 0.0418(5) Uani 1 1 d . . . . .
H7 H 0.3832 0.1215 0.3556 0.050 Uiso 1 1 calc R U . . .
C8 C 0.37869(15) 0.04346(9) 0.76560(12) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.2992 0.0145 0.7311 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5893(3) 0.15588(12) 0.35901(19) 0.0503(6) Uani 1 1 d . . . . .
H11A H 0.5853 0.1664 0.2781 0.075 Uiso 1 1 calc R U . . .
H11B H 0.6486 0.1899 0.4013 0.075 Uiso 1 1 calc R U . . .
H11C H 0.6301 0.1102 0.3726 0.075 Uiso 1 1 calc R U . . .
C12 C 0.3686(3) 0.22629(12) 0.3743(2) 0.0613(8) Uani 1 1 d . . . . .
H12A H 0.3657 0.2365 0.2933 0.092 Uiso 1 1 calc R U . . .
H12B H 0.2715 0.2244 0.3973 0.092 Uiso 1 1 calc R U . . .
H12C H 0.4218 0.2622 0.4171 0.092 Uiso 1 1 calc R U . . .
C13 C 0.50108(19) -0.00300(10) 0.80520(16) 0.0328(4) Uani 1 1 d . . . . .
H13A H 0.4711 -0.0344 0.8630 0.049 Uiso 1 1 calc R U . . .
H13B H 0.5304 -0.0294 0.7410 0.049 Uiso 1 1 calc R U . . .
H13C H 0.5810 0.0247 0.8373 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3256(2) 0.08313(15) 0.86376(17) 0.0506(7) Uani 1 1 d . . . . .
H14A H 0.2966 0.0510 0.9208 0.076 Uiso 1 1 calc R U . . .
H14B H 0.4018 0.1126 0.8975 0.076 Uiso 1 1 calc R U . . .
H14C H 0.2443 0.1114 0.8363 0.076 Uiso 1 1 calc R U . . .
I1 I 0.7500 0.34667(2) 0.5000 0.02936(7) Uani 1 2 d S T P . .


_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
P1 C1 1.8193(14) . ?
P1 C1 1.8194(14) 2_556 ?
N1 C1 1.356(2) . ?
N1 C3 1.384(2) . ?
N1 C7 1.478(2) . ?
N2 C1 1.3588(18) . ?
N2 C4 1.381(2) . ?
N2 C8 1.472(2) . ?
C3 C4 1.345(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C7 C11 1.513(4) . ?
C7 C12 1.520(3) . ?
C7 H7 1.0000 . ?
C8 C13 1.514(2) . ?
C8 C14 1.520(2) . ?
C8 H8 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C1 P1 C1 97.37(9) . 2_556 ?
C1 N1 C3 109.98(14) . . ?
C1 N1 C7 126.12(13) . . ?
C3 N1 C7 123.65(15) . . ?
C1 N2 C4 110.03(13) . . ?
C1 N2 C8 126.00(12) . . ?
C4 N2 C8 123.96(13) . . ?
N1 C1 N2 105.59(12) . . ?
N1 C1 P1 128.80(11) . . ?
N2 C1 P1 125.44(11) . . ?
C4 C3 N1 107.17(15) . . ?
C4 C3 H3 126.4 . . ?
N1 C3 H3 126.4 . . ?
C3 C4 N2 107.20(14) . . ?
C3 C4 H4 126.4 . . ?
N2 C4 H4 126.4 . . ?
N1 C7 C11 109.98(16) . . ?
N1 C7 C12 109.8(2) . . ?
C11 C7 C12 112.30(17) . . ?
N1 C7 H7 108.2 . . ?
C11 C7 H7 108.2 . . ?
C12 C7 H7 108.2 . . ?
N2 C8 C13 109.79(12) . . ?
N2 C8 C14 110.43(16) . . ?
C13 C8 C14 111.18(15) . . ?
N2 C8 H8 108.5 . . ?
C13 C8 H8 108.5 . . ?
C14 C8 H8 108.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -1.2(2) . . . . ?
C7 N1 C1 N2 173.14(18) . . . . ?
C3 N1 C1 P1 -176.65(14) . . . . ?
C7 N1 C1 P1 -2.3(3) . . . . ?
C4 N2 C1 N1 0.15(18) . . . . ?
C8 N2 C1 N1 -178.97(14) . . . . ?
C4 N2 C1 P1 175.76(12) . . . . ?
C8 N2 C1 P1 -3.4(2) . . . . ?
C1 P1 C1 N1 -56.56(13) 2_556 . . . ?
C1 P1 C1 N2 128.86(16) 2_556 . . . ?
C1 N1 C3 C4 1.9(2) . . . . ?
C7 N1 C3 C4 -172.66(19) . . . . ?
N1 C3 C4 N2 -1.7(2) . . . . ?
C1 N2 C4 C3 1.0(2) . . . . ?
C8 N2 C4 C3 -179.85(16) . . . . ?
C1 N1 C7 C11 -123.16(19) . . . . ?
C3 N1 C7 C11 50.5(3) . . . . ?
C1 N1 C7 C12 112.8(2) . . . . ?
C3 N1 C7 C12 -73.6(2) . . . . ?
C1 N2 C8 C13 112.33(16) . . . . ?
C4 N2 C8 C13 -66.68(19) . . . . ?
C1 N2 C8 C14 -124.74(16) . . . . ?
C4 N2 C8 C14 56.26(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 I1 0.95 3.23 4.1596(18) 167.2 .
C4 H4 I1 0.95 3.07 4.0079(16) 168.6 7_656

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_g362_mn
_database_code_depnum_ccdc_archive 'CCDC 1842619'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H17 I N2 P, I'
_chemical_formula_sum            'C9 H17 I2 N2 P'
_chemical_formula_weight         438.01

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7774(5)
_cell_length_b                   8.4078(6)
_cell_length_c                   11.6208(8)
_cell_angle_alpha                84.753(4)
_cell_angle_beta                 79.435(3)
_cell_angle_gamma                78.409(3)
_cell_volume                     730.60(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3973
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      30.6

_exptl_crystal_description       blocks
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.355
_exptl_absorpt_coefficient_mu    4.386
_shelx_estimated_absorpt_T_min   0.256
_shelx_estimated_absorpt_T_max   0.305
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2355
_exptl_absorpt_correction_T_max  0.3927
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17876
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         30.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4468
_reflns_number_gt                3970
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²+0.7642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0132(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4468
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0491
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.80219(2) 0.27670(2) 0.39613(2) 0.02393(5) Uani 1 1 d . . . . .
I2 I 0.74618(2) 0.13377(2) -0.05131(2) 0.02595(5) Uani 1 1 d . . . . .
P1 P 0.77936(8) 0.21999(9) 0.15696(6) 0.02751(14) Uani 1 1 d D . . . .
H1 H 0.906(3) 0.111(3) 0.167(3) 0.041 Uiso 1 1 d D U . . .
N1 N 0.5945(2) -0.0268(2) 0.27442(16) 0.0183(3) Uani 1 1 d . . . . .
N2 N 0.4227(2) 0.2047(2) 0.24418(16) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.5930(3) 0.1253(2) 0.22717(17) 0.0163(4) Uani 1 1 d . . . . .
C2 C 0.4230(3) -0.0428(3) 0.32321(19) 0.0216(4) Uani 1 1 d . . . . .
H2 H 0.3868 -0.1377 0.3627 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3159(3) 0.1015(3) 0.3044(2) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.1904 0.1270 0.3282 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7520(3) -0.1600(3) 0.2745(2) 0.0260(5) Uani 1 1 d . . . . .
H4 H 0.8607 -0.1150 0.2389 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3577(3) 0.3754(3) 0.2051(2) 0.0210(4) Uani 1 1 d . . . . .
H5 H 0.4607 0.4194 0.1579 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7374(6) -0.2921(4) 0.2000(3) 0.0554(11) Uani 1 1 d . . . . .
H6A H 0.8415 -0.3799 0.2003 0.083 Uiso 1 1 calc R U . . .
H6B H 0.6290 -0.3350 0.2317 0.083 Uiso 1 1 calc R U . . .
H6C H 0.7322 -0.2477 0.1195 0.083 Uiso 1 1 calc R U . . .
C7 C 0.7696(6) -0.2215(4) 0.3987(3) 0.0530(10) Uani 1 1 d . . . . .
H7A H 0.8738 -0.3093 0.3980 0.079 Uiso 1 1 calc R U . . .
H7B H 0.7842 -0.1324 0.4427 0.079 Uiso 1 1 calc R U . . .
H7C H 0.6623 -0.2626 0.4361 0.079 Uiso 1 1 calc R U . . .
C8 C 0.2207(4) 0.3790(3) 0.1266(2) 0.0331(6) Uani 1 1 d . . . . .
H8A H 0.1773 0.4917 0.1005 0.050 Uiso 1 1 calc R U . . .
H8B H 0.2757 0.3155 0.0582 0.050 Uiso 1 1 calc R U . . .
H8C H 0.1208 0.3321 0.1704 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2850(4) 0.4773(3) 0.3107(2) 0.0296(5) Uani 1 1 d . . . . .
H9A H 0.2423 0.5900 0.2842 0.044 Uiso 1 1 calc R U . . .
H9B H 0.1863 0.4337 0.3595 0.044 Uiso 1 1 calc R U . . .
H9C H 0.3796 0.4741 0.3567 0.044 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 P1 2.9053(7) . ?
I2 P1 2.6599(7) . ?
P1 C1 1.819(2) . ?
P1 H1 1.220(18) . ?
N1 C1 1.344(3) . ?
N1 C2 1.379(3) . ?
N1 C4 1.485(3) . ?
N2 C1 1.346(3) . ?
N2 C3 1.378(3) . ?
N2 C5 1.482(3) . ?
C2 C3 1.351(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C6 1.503(4) . ?
C4 C7 1.509(4) . ?
C4 H4 1.0000 . ?
C5 C8 1.518(4) . ?
C5 C9 1.518(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C1 P1 I2 90.53(7) . . ?
C1 P1 I1 83.65(7) . . ?
I2 P1 I1 172.92(3) . . ?
C1 P1 H1 101.8(17) . . ?
I2 P1 H1 93.6(16) . . ?
I1 P1 H1 83.7(16) . . ?
C1 N1 C2 109.04(18) . . ?
C1 N1 C4 126.89(19) . . ?
C2 N1 C4 124.07(19) . . ?
C1 N2 C3 109.11(18) . . ?
C1 N2 C5 126.19(18) . . ?
C3 N2 C5 124.70(18) . . ?
N1 C1 N2 107.40(18) . . ?
N1 C1 P1 129.03(16) . . ?
N2 C1 P1 123.53(16) . . ?
C3 C2 N1 107.30(19) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 107.16(19) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N1 C4 C6 109.7(2) . . ?
N1 C4 C7 110.0(2) . . ?
C6 C4 C7 112.5(2) . . ?
N1 C4 H4 108.2 . . ?
C6 C4 H4 108.2 . . ?
C7 C4 H4 108.2 . . ?
N2 C5 C8 109.17(19) . . ?
N2 C5 C9 109.92(19) . . ?
C8 C5 C9 112.8(2) . . ?
N2 C5 H5 108.3 . . ?
C8 C5 H5 108.3 . . ?
C9 C5 H5 108.3 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.8(2) . . . . ?
C4 N1 C1 N2 178.5(2) . . . . ?
C2 N1 C1 P1 176.92(17) . . . . ?
C4 N1 C1 P1 -3.8(3) . . . . ?
C3 N2 C1 N1 0.8(2) . . . . ?
C5 N2 C1 N1 -179.14(19) . . . . ?
C3 N2 C1 P1 -177.06(16) . . . . ?
C5 N2 C1 P1 3.0(3) . . . . ?
I2 P1 C1 N1 92.15(19) . . . . ?
I1 P1 C1 N1 -83.82(19) . . . . ?
I2 P1 C1 N2 -90.49(18) . . . . ?
I1 P1 C1 N2 93.55(18) . . . . ?
C1 N1 C2 C3 0.5(3) . . . . ?
C4 N1 C2 C3 -178.8(2) . . . . ?
N1 C2 C3 N2 0.0(3) . . . . ?
C1 N2 C3 C2 -0.5(3) . . . . ?
C5 N2 C3 C2 179.4(2) . . . . ?
C1 N1 C4 C6 -113.0(3) . . . . ?
C2 N1 C4 C6 66.1(3) . . . . ?
C1 N1 C4 C7 122.8(3) . . . . ?
C2 N1 C4 C7 -58.1(3) . . . . ?
C1 N2 C5 C8 122.3(2) . . . . ?
C3 N2 C5 C8 -57.7(3) . . . . ?
C1 N2 C5 C9 -113.5(2) . . . . ?
C3 N2 C5 C9 66.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
P1 H1 I2 1.220(18) 3.21(2) 4.3089(8) 150(2) 2_755
C2 H2 I1 0.95 3.16 3.961(2) 143.6 2_656
C3 H3 I1 0.95 3.02 3.953(2) 168.7 1_455
C8 H8A I2 0.98 3.30 4.159(3) 147.3 2_665

_refine_diff_density_max         0.803
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.122


# start Validation Reply Form
_vrf_PLAT230_g362_mn             
;
PROBLEM: Hirshfeld Test Diff for    I2     --  P1      ..       15.3 s.u.  
RESPONSE: bond between P and terminal one I-atom (I2) in CP(H)I2 moiety
;
# end Validation Reply Form
####################################################################### 
# 
# 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_g453_mn
_database_code_depnum_ccdc_archive 'CCDC 1842622'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H37 I1 N2 P, I3'
_chemical_formula_sum            'C27 H37 I4 N2 P'
_chemical_formula_weight         928.15

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.5136(7)
_cell_length_b                   16.6700(10)
_cell_length_c                   16.8720(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.146(3)
_cell_angle_gamma                90
_cell_volume                     3344.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    9668
_cell_measurement_theta_min      2.104
_cell_measurement_theta_max      30.538

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    3.792
_shelx_estimated_absorpt_T_min   0.344
_shelx_estimated_absorpt_T_max   0.579
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3762
_exptl_absorpt_correction_T_max  0.6350
_exptl_absorpt_process_details   'BLESSING 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36150
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         30.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10127
_reflns_number_gt                9668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+9.5364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10127
_refine_ls_number_parameters     310
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.30634(13) 0.53048(9) 0.42693(10) 0.0266(3) Uani 1 1 d D . . . .
H1A H 0.328(7) 0.474(3) 0.388(5) 0.032 Uiso 1 1 d D U . . .
I1 I 0.50601(3) 0.53471(3) 0.50673(3) 0.03586(10) Uani 1 1 d . . . . .
C1 C 0.2971(4) 0.6061(3) 0.3466(3) 0.0179(8) Uani 1 1 d . . . . .
N1 N 0.2514(4) 0.6804(3) 0.3428(3) 0.0201(8) Uani 1 1 d . . . . .
N2 N 0.3205(4) 0.5945(3) 0.2751(3) 0.0179(8) Uani 1 1 d . . . . .
C2 C 0.2453(5) 0.7149(3) 0.2674(4) 0.0237(10) Uani 1 1 d . . . . .
H2 H 0.2161 0.7665 0.2487 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2885(5) 0.6617(3) 0.2247(4) 0.0244(10) Uani 1 1 d . . . . .
H3 H 0.2955 0.6690 0.1707 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3699(4) 0.5234(3) 0.2515(3) 0.0196(9) Uani 1 1 d . . . . .
C5 C 0.4869(5) 0.5232(3) 0.2656(4) 0.0225(10) Uani 1 1 d . . . . .
C6 C 0.5320(6) 0.4531(4) 0.2440(5) 0.0329(13) Uani 1 1 d . . . . .
H6 H 0.6108 0.4495 0.2539 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4655(7) 0.3894(4) 0.2091(5) 0.0412(16) Uani 1 1 d . . . . .
H7 H 0.4986 0.3431 0.1937 0.049 Uiso 1 1 calc R U . . .
C8 C 0.3485(6) 0.3913(4) 0.1954(5) 0.0348(13) Uani 1 1 d . . . . .
H8 H 0.3037 0.3461 0.1714 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2985(5) 0.4585(3) 0.2167(4) 0.0273(11) Uani 1 1 d . . . . .
C10 C 0.2079(5) 0.7159(3) 0.4050(4) 0.0237(10) Uani 1 1 d . . . . .
C11 C 0.2780(5) 0.7687(3) 0.4624(4) 0.0284(11) Uani 1 1 d . . . . .
C12 C 0.2327(6) 0.8053(4) 0.5201(5) 0.0414(16) Uani 1 1 d . . . . .
H12 H 0.2755 0.8434 0.5590 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1247(7) 0.7851(6) 0.5192(5) 0.049(2) Uani 1 1 d . . . . .
H13 H 0.0954 0.8087 0.5593 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0587(6) 0.7319(5) 0.4622(5) 0.0426(17) Uani 1 1 d . . . . .
H14 H -0.0146 0.7194 0.4641 0.051 Uiso 1 1 calc R U . . .
C15 C 0.0980(5) 0.6963(4) 0.4020(4) 0.0284(11) Uani 1 1 d . . . . .
C16 C 0.5594(5) 0.5958(4) 0.2975(4) 0.0277(11) Uani 1 1 d . . . . .
H16 H 0.5230 0.6288 0.3314 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5696(6) 0.6472(4) 0.2249(5) 0.0398(15) Uani 1 1 d . . . . .
H17A H 0.6170 0.6940 0.2469 0.060 Uiso 1 1 calc R U . . .
H17B H 0.6037 0.6153 0.1903 0.060 Uiso 1 1 calc R U . . .
H17C H 0.4948 0.6651 0.1911 0.060 Uiso 1 1 calc R U . . .
C18 C 0.6786(5) 0.5735(5) 0.3527(4) 0.0390(16) Uani 1 1 d . . . . .
H18A H 0.7222 0.6226 0.3718 0.059 Uiso 1 1 calc R U . . .
H18B H 0.6741 0.5428 0.4011 0.059 Uiso 1 1 calc R U . . .
H18C H 0.7156 0.5410 0.3204 0.059 Uiso 1 1 calc R U . . .
C19 C 0.1725(5) 0.4626(4) 0.1989(4) 0.0282(11) Uani 1 1 d . . . . .
H19 H 0.1549 0.5095 0.2296 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1153(7) 0.4752(5) 0.1055(5) 0.0458(18) Uani 1 1 d . . . . .
H20A H 0.0336 0.4779 0.0942 0.069 Uiso 1 1 calc R U . . .
H20B H 0.1419 0.5255 0.0881 0.069 Uiso 1 1 calc R U . . .
H20C H 0.1336 0.4304 0.0745 0.069 Uiso 1 1 calc R U . . .
C21 C 0.1261(6) 0.3869(5) 0.2271(5) 0.0423(17) Uani 1 1 d . . . . .
H21A H 0.0445 0.3920 0.2144 0.063 Uiso 1 1 calc R U . . .
H21B H 0.1430 0.3403 0.1975 0.063 Uiso 1 1 calc R U . . .
H21C H 0.1610 0.3797 0.2873 0.063 Uiso 1 1 calc R U . . .
C22 C 0.3958(5) 0.7902(4) 0.4623(4) 0.0309(12) Uani 1 1 d . . . . .
H22 H 0.4203 0.7491 0.4283 0.037 Uiso 1 1 calc R U . . .
C23 C 0.3964(7) 0.8726(5) 0.4214(6) 0.052(2) Uani 1 1 d . . . . .
H23A H 0.3421 0.8724 0.3652 0.077 Uiso 1 1 calc R U . . .
H23B H 0.3758 0.9141 0.4551 0.077 Uiso 1 1 calc R U . . .
H23C H 0.4718 0.8836 0.4180 0.077 Uiso 1 1 calc R U . . .
C24 C 0.4797(7) 0.7898(5) 0.5493(5) 0.0452(17) Uani 1 1 d . . . . .
H24A H 0.5543 0.8040 0.5464 0.068 Uiso 1 1 calc R U . . .
H24B H 0.4566 0.8290 0.5841 0.068 Uiso 1 1 calc R U . . .
H24C H 0.4823 0.7362 0.5737 0.068 Uiso 1 1 calc R U . . .
C25 C 0.0231(5) 0.6391(4) 0.3393(4) 0.0265(11) Uani 1 1 d . . . . .
H25 H 0.0654 0.6208 0.3011 0.032 Uiso 1 1 calc R U . . .
C26 C -0.0836(6) 0.6834(4) 0.2859(5) 0.0404(15) Uani 1 1 d . . . . .
H26A H -0.1317 0.6460 0.2455 0.061 Uiso 1 1 calc R U . . .
H26B H -0.1249 0.7043 0.3222 0.061 Uiso 1 1 calc R U . . .
H26C H -0.0620 0.7279 0.2562 0.061 Uiso 1 1 calc R U . . .
C27 C -0.0070(6) 0.5655(4) 0.3805(5) 0.0373(14) Uani 1 1 d . . . . .
H27A H -0.0554 0.5302 0.3378 0.056 Uiso 1 1 calc R U . . .
H27B H 0.0619 0.5367 0.4110 0.056 Uiso 1 1 calc R U . . .
H27C H -0.0469 0.5819 0.4195 0.056 Uiso 1 1 calc R U . . .
I1A I 0.27786(4) 0.32883(3) 0.48734(3) 0.03662(11) Uani 1 1 d . . . . .
I2A I 0.29413(3) 0.17545(2) 0.57103(2) 0.02339(7) Uani 1 1 d . . . . .
I3A I 0.29746(4) 0.01931(2) 0.65041(3) 0.03529(10) 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
P1 C1 1.828(5) . ?
P1 I1 2.4424(16) . ?
P1 H1A 1.22(3) . ?
C1 N2 1.340(6) . ?
C1 N1 1.358(6) . ?
N1 C2 1.376(7) . ?
N1 C10 1.450(6) . ?
N2 C3 1.388(7) . ?
N2 C4 1.449(6) . ?
C2 C3 1.357(8) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.408(7) . ?
C4 C9 1.411(8) . ?
C5 C6 1.395(8) . ?
C5 C16 1.507(8) . ?
C6 C7 1.364(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(8) . ?
C8 H8 0.9500 . ?
C9 C19 1.511(8) . ?
C10 C11 1.397(8) . ?
C10 C15 1.399(8) . ?
C11 C12 1.409(9) . ?
C11 C22 1.519(8) . ?
C12 C13 1.388(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(8) . ?
C14 H14 0.9500 . ?
C15 C25 1.513(8) . ?
C16 C17 1.533(9) . ?
C16 C18 1.538(9) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.526(9) . ?
C19 C20 1.528(10) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C24 1.516(10) . ?
C22 C23 1.537(10) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C27 1.516(9) . ?
C25 C26 1.546(9) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
I1A I2A 2.8973(5) . ?
I1A H1A 3.12(8) . ?
I2A I3A 2.9215(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
C1 P1 I1 101.90(17) . . ?
C1 P1 H1A 96(4) . . ?
I1 P1 H1A 88(4) . . ?
N2 C1 N1 107.2(4) . . ?
N2 C1 P1 125.9(4) . . ?
N1 C1 P1 126.3(4) . . ?
C1 N1 C2 109.0(4) . . ?
C1 N1 C10 125.9(4) . . ?
C2 N1 C10 125.0(5) . . ?
C1 N2 C3 109.5(4) . . ?
C1 N2 C4 126.7(4) . . ?
C3 N2 C4 123.8(4) . . ?
C3 C2 N1 107.6(5) . . ?
C3 C2 H2 126.2 . . ?
N1 C2 H2 126.2 . . ?
C2 C3 N2 106.7(5) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
C5 C4 C9 124.0(5) . . ?
C5 C4 N2 117.8(5) . . ?
C9 C4 N2 118.2(5) . . ?
C6 C5 C4 116.2(5) . . ?
C6 C5 C16 121.3(5) . . ?
C4 C5 C16 122.4(5) . . ?
C7 C6 C5 121.6(6) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 121.1(6) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 120.4(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 116.8(6) . . ?
C8 C9 C19 120.9(5) . . ?
C4 C9 C19 122.3(5) . . ?
C11 C10 C15 124.8(5) . . ?
C11 C10 N1 117.5(5) . . ?
C15 C10 N1 117.7(5) . . ?
C10 C11 C12 116.8(6) . . ?
C10 C11 C22 123.3(5) . . ?
C12 C11 C22 119.9(6) . . ?
C13 C12 C11 119.1(6) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 122.3(6) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C15 120.8(6) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 116.1(6) . . ?
C14 C15 C25 119.8(5) . . ?
C10 C15 C25 124.1(5) . . ?
C5 C16 C17 110.7(5) . . ?
C5 C16 C18 112.6(6) . . ?
C17 C16 C18 108.2(5) . . ?
C5 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
C18 C16 H16 108.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 C21 112.1(5) . . ?
C9 C19 C20 109.6(6) . . ?
C21 C19 C20 109.5(6) . . ?
C9 C19 H19 108.5 . . ?
C21 C19 H19 108.5 . . ?
C20 C19 H19 108.5 . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 C22 C11 112.2(6) . . ?
C24 C22 C23 109.8(6) . . ?
C11 C22 C23 110.6(6) . . ?
C24 C22 H22 108.0 . . ?
C11 C22 H22 108.0 . . ?
C23 C22 H22 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 C27 112.2(5) . . ?
C15 C25 C26 109.9(5) . . ?
C27 C25 C26 111.2(5) . . ?
C15 C25 H25 107.8 . . ?
C27 C25 H25 107.8 . . ?
C26 C25 H25 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
I2A I1A H1A 162.2(11) . . ?
I1A I2A I3A 176.845(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 P1 C1 N2 83.2(4) . . . . ?
I1 P1 C1 N1 -106.3(4) . . . . ?
N2 C1 N1 C2 0.7(6) . . . . ?
P1 C1 N1 C2 -171.2(4) . . . . ?
N2 C1 N1 C10 176.4(5) . . . . ?
P1 C1 N1 C10 4.4(8) . . . . ?
N1 C1 N2 C3 -0.6(6) . . . . ?
P1 C1 N2 C3 171.4(4) . . . . ?
N1 C1 N2 C4 -179.8(5) . . . . ?
P1 C1 N2 C4 -7.8(7) . . . . ?
C1 N1 C2 C3 -0.5(6) . . . . ?
C10 N1 C2 C3 -176.3(5) . . . . ?
N1 C2 C3 N2 0.2(6) . . . . ?
C1 N2 C3 C2 0.2(6) . . . . ?
C4 N2 C3 C2 179.5(5) . . . . ?
C1 N2 C4 C5 -96.2(6) . . . . ?
C3 N2 C4 C5 84.8(7) . . . . ?
C1 N2 C4 C9 83.1(7) . . . . ?
C3 N2 C4 C9 -96.0(6) . . . . ?
C9 C4 C5 C6 -0.8(8) . . . . ?
N2 C4 C5 C6 178.4(5) . . . . ?
C9 C4 C5 C16 175.7(5) . . . . ?
N2 C4 C5 C16 -5.0(8) . . . . ?
C4 C5 C6 C7 1.8(10) . . . . ?
C16 C5 C6 C7 -174.8(7) . . . . ?
C5 C6 C7 C8 -1.7(12) . . . . ?
C6 C7 C8 C9 0.6(12) . . . . ?
C7 C8 C9 C4 0.4(10) . . . . ?
C7 C8 C9 C19 177.3(7) . . . . ?
C5 C4 C9 C8 -0.3(9) . . . . ?
N2 C4 C9 C8 -179.5(5) . . . . ?
C5 C4 C9 C19 -177.2(5) . . . . ?
N2 C4 C9 C19 3.6(8) . . . . ?
C1 N1 C10 C11 98.5(7) . . . . ?
C2 N1 C10 C11 -86.5(7) . . . . ?
C1 N1 C10 C15 -82.9(7) . . . . ?
C2 N1 C10 C15 92.1(7) . . . . ?
C15 C10 C11 C12 -1.1(10) . . . . ?
N1 C10 C11 C12 177.3(6) . . . . ?
C15 C10 C11 C22 -178.3(6) . . . . ?
N1 C10 C11 C22 0.1(9) . . . . ?
C10 C11 C12 C13 2.6(11) . . . . ?
C22 C11 C12 C13 179.9(8) . . . . ?
C11 C12 C13 C14 -1.9(14) . . . . ?
C12 C13 C14 C15 -0.4(15) . . . . ?
C13 C14 C15 C10 1.9(12) . . . . ?
C13 C14 C15 C25 -179.0(8) . . . . ?
C11 C10 C15 C14 -1.1(10) . . . . ?
N1 C10 C15 C14 -179.5(6) . . . . ?
C11 C10 C15 C25 179.9(6) . . . . ?
N1 C10 C15 C25 1.5(9) . . . . ?
C6 C5 C16 C17 85.3(7) . . . . ?
C4 C5 C16 C17 -91.0(7) . . . . ?
C6 C5 C16 C18 -36.0(8) . . . . ?
C4 C5 C16 C18 147.7(5) . . . . ?
C8 C9 C19 C21 47.8(9) . . . . ?
C4 C9 C19 C21 -135.4(6) . . . . ?
C8 C9 C19 C20 -73.9(8) . . . . ?
C4 C9 C19 C20 102.8(7) . . . . ?
C10 C11 C22 C24 -136.1(7) . . . . ?
C12 C11 C22 C24 46.8(9) . . . . ?
C10 C11 C22 C23 100.9(8) . . . . ?
C12 C11 C22 C23 -76.2(9) . . . . ?
C14 C15 C25 C27 -62.4(9) . . . . ?
C10 C15 C25 C27 116.6(7) . . . . ?
C14 C15 C25 C26 61.8(8) . . . . ?
C10 C15 C25 C26 -119.2(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 I1A 0.95 3.03 3.968(6) 168.8 2_564
C3 H3 I2A 0.95 3.09 3.769(5) 130.1 2_564

_refine_diff_density_max         2.324
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_g407_mn
_database_code_depnum_ccdc_archive 'CCDC 1842620'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 I2 N2 P'
_chemical_formula_sum            'C21 H25 I2 N2 P'
_chemical_formula_weight         590.20

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.2530(6)
_cell_length_b                   15.3097(11)
_cell_length_c                   16.0029(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2267.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4640
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      28.1

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    2.852
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.668
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5513
_exptl_absorpt_correction_T_max  0.6920
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20732
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         28.182
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5584
_reflns_number_gt                4639
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.3721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5584
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.38239(5) 0.41891(3) 0.13288(3) 0.03100(11) Uani 1 1 d . . . . .
I2 I 0.70821(5) 0.29803(3) 0.39735(3) 0.03282(12) Uani 1 1 d . . . . .
P1 P 0.5248(2) 0.36535(13) 0.28103(12) 0.0336(4) Uani 1 1 d D . . . .
H1P H 0.503(7) 0.287(2) 0.263(4) 0.050 Uiso 1 1 d D U . . .
C1 C 0.3637(6) 0.3720(3) 0.3499(3) 0.0159(12) Uani 1 1 d . . . . .
N1 N 0.3397(5) 0.4329(3) 0.4099(3) 0.0174(10) Uani 1 1 d . . . . .
N2 N 0.2479(5) 0.3191(3) 0.3497(3) 0.0158(11) Uani 1 1 d . . . . .
C2 C 0.4481(6) 0.5792(4) 0.3934(4) 0.0205(12) Uani 1 1 d . . . . .
C3 C 0.4380(6) 0.5013(4) 0.4387(4) 0.0173(13) Uani 1 1 d . . . . .
C4 C 0.5121(6) 0.4867(4) 0.5136(4) 0.0200(13) Uani 1 1 d . . . . .
C5 C 0.6258(7) 0.6295(4) 0.4959(4) 0.0241(13) Uani 1 1 d . . . . .
C6 C 0.1126(7) 0.2617(4) 0.2312(4) 0.0216(13) Uani 1 1 d . . . . .
C7 C 0.2161(7) 0.2468(3) 0.2927(4) 0.0176(12) Uani 1 1 d . . . . .
C8 C 0.2835(7) 0.1662(4) 0.3053(4) 0.0209(13) Uani 1 1 d . . . . .
C9 C 0.1452(7) 0.1109(4) 0.1866(4) 0.0275(15) Uani 1 1 d . . . . .
C10 C 0.2098(6) 0.4178(4) 0.4475(3) 0.0185(11) Uani 1 1 d . . . . .
H10 H 0.1686 0.4508 0.4917 0.022 Uiso 1 1 calc R U . . .
C11 C 0.1501(6) 0.3469(3) 0.4101(4) 0.0182(12) Uani 1 1 d . . . . .
H11 H 0.0592 0.3212 0.4228 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6082(7) 0.5512(4) 0.5398(4) 0.0223(13) Uani 1 1 d . . . . .
H12 H 0.6635 0.5416 0.5890 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5436(6) 0.6431(4) 0.4236(4) 0.0238(14) Uani 1 1 d . . . . .
H13 H 0.5527 0.6967 0.3943 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2446(7) 0.0990(4) 0.2499(4) 0.0262(15) Uani 1 1 d . . . . .
H14 H 0.2883 0.0432 0.2562 0.031 Uiso 1 1 calc R U . . .
C15 C 0.0804(6) 0.1922(4) 0.1784(4) 0.0282(15) Uani 1 1 d . . . . .
H15 H 0.0116 0.2007 0.1351 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3567(7) 0.5979(4) 0.3172(4) 0.0257(15) Uani 1 1 d . . . . .
H16A H 0.3847 0.5584 0.2718 0.039 Uiso 1 1 calc R U . . .
H16B H 0.3717 0.6586 0.2996 0.039 Uiso 1 1 calc R U . . .
H16C H 0.2545 0.5889 0.3308 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4844(7) 0.4067(4) 0.5666(4) 0.0280(15) Uani 1 1 d . . . . .
H17A H 0.5623 0.4001 0.6076 0.042 Uiso 1 1 calc R U . . .
H17B H 0.4809 0.3548 0.5307 0.042 Uiso 1 1 calc R U . . .
H17C H 0.3919 0.4132 0.5958 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7324(7) 0.6976(4) 0.5252(4) 0.0327(16) Uani 1 1 d . . . . .
H18A H 0.7171 0.7093 0.5848 0.049 Uiso 1 1 calc R U . . .
H18B H 0.7181 0.7516 0.4934 0.049 Uiso 1 1 calc R U . . .
H18C H 0.8310 0.6762 0.5165 0.049 Uiso 1 1 calc R U . . .
C19 C 0.0328(7) 0.3473(4) 0.2209(4) 0.0311(16) Uani 1 1 d . . . . .
H19A H 0.0093 0.3561 0.1618 0.047 Uiso 1 1 calc R U . . .
H19B H 0.0939 0.3953 0.2405 0.047 Uiso 1 1 calc R U . . .
H19C H -0.0567 0.3457 0.2537 0.047 Uiso 1 1 calc R U . . .
C20 C 0.3836(7) 0.1486(4) 0.3774(4) 0.0287(14) Uani 1 1 d . . . . .
H20A H 0.3789 0.0866 0.3924 0.043 Uiso 1 1 calc R U . . .
H20B H 0.3544 0.1841 0.4255 0.043 Uiso 1 1 calc R U . . .
H20C H 0.4828 0.1636 0.3614 0.043 Uiso 1 1 calc R U . . .
C21 C 0.1042(9) 0.0366(4) 0.1271(5) 0.045(2) Uani 1 1 d . . . . .
H21A H 0.0258 0.0021 0.1517 0.068 Uiso 1 1 calc R U . . .
H21B H 0.1884 -0.0010 0.1178 0.068 Uiso 1 1 calc R U . . .
H21C H 0.0721 0.0611 0.0737 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 P1 2.8336(19) . ?
I2 P1 2.7217(19) . ?
P1 C1 1.857(6) . ?
P1 H1P 1.25(3) . ?
C1 N2 1.343(7) . ?
C1 N1 1.357(7) . ?
N1 C10 1.364(7) . ?
N1 C3 1.461(7) . ?
N2 C11 1.391(7) . ?
N2 C7 1.463(7) . ?
C2 C3 1.398(8) . ?
C2 C13 1.404(8) . ?
C2 C16 1.512(8) . ?
C3 C4 1.398(8) . ?
C4 C12 1.393(8) . ?
C4 C17 1.513(8) . ?
C5 C12 1.399(8) . ?
C5 C13 1.400(9) . ?
C5 C18 1.510(8) . ?
C6 C15 1.391(8) . ?
C6 C7 1.391(8) . ?
C6 C19 1.513(8) . ?
C7 C8 1.398(8) . ?
C8 C14 1.405(8) . ?
C8 C20 1.505(9) . ?
C9 C14 1.379(9) . ?
C9 C15 1.388(9) . ?
C9 C21 1.532(9) . ?
C10 C11 1.357(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C1 P1 I2 96.63(18) . . ?
C1 P1 I1 96.17(18) . . ?
I2 P1 I1 166.36(7) . . ?
C1 P1 H1P 93(3) . . ?
I2 P1 H1P 84(3) . . ?
I1 P1 H1P 90(3) . . ?
N2 C1 N1 106.6(5) . . ?
N2 C1 P1 127.3(4) . . ?
N1 C1 P1 126.1(4) . . ?
C1 N1 C10 109.8(5) . . ?
C1 N1 C3 127.9(5) . . ?
C10 N1 C3 122.1(5) . . ?
C1 N2 C11 109.4(4) . . ?
C1 N2 C7 128.2(5) . . ?
C11 N2 C7 122.2(4) . . ?
C3 C2 C13 117.2(6) . . ?
C3 C2 C16 122.9(5) . . ?
C13 C2 C16 119.8(5) . . ?
C4 C3 C2 123.2(5) . . ?
C4 C3 N1 117.5(5) . . ?
C2 C3 N1 119.2(5) . . ?
C12 C4 C3 117.3(5) . . ?
C12 C4 C17 120.9(5) . . ?
C3 C4 C17 121.8(5) . . ?
C12 C5 C13 118.6(6) . . ?
C12 C5 C18 120.8(6) . . ?
C13 C5 C18 120.6(6) . . ?
C15 C6 C7 116.9(6) . . ?
C15 C6 C19 119.4(6) . . ?
C7 C6 C19 123.7(5) . . ?
C6 C7 C8 123.6(5) . . ?
C6 C7 N2 117.1(5) . . ?
C8 C7 N2 119.2(5) . . ?
C7 C8 C14 116.2(6) . . ?
C7 C8 C20 122.9(5) . . ?
C14 C8 C20 120.7(5) . . ?
C14 C9 C15 118.5(6) . . ?
C14 C9 C21 121.5(6) . . ?
C15 C9 C21 120.0(7) . . ?
C11 C10 N1 107.5(5) . . ?
C11 C10 H10 126.3 . . ?
N1 C10 H10 126.3 . . ?
C10 C11 N2 106.6(5) . . ?
C10 C11 H11 126.7 . . ?
N2 C11 H11 126.7 . . ?
C4 C12 C5 122.1(6) . . ?
C4 C12 H12 119.0 . . ?
C5 C12 H12 119.0 . . ?
C5 C13 C2 121.5(6) . . ?
C5 C13 H13 119.2 . . ?
C2 C13 H13 119.2 . . ?
C9 C14 C8 122.5(6) . . ?
C9 C14 H14 118.8 . . ?
C8 C14 H14 118.8 . . ?
C9 C15 C6 122.4(6) . . ?
C9 C15 H15 118.8 . . ?
C6 C15 H15 118.8 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I2 P1 C1 N2 -104.7(5) . . . . ?
I1 P1 C1 N2 70.5(5) . . . . ?
I2 P1 C1 N1 76.4(5) . . . . ?
I1 P1 C1 N1 -108.4(4) . . . . ?
N2 C1 N1 C10 0.5(6) . . . . ?
P1 C1 N1 C10 179.5(4) . . . . ?
N2 C1 N1 C3 175.1(5) . . . . ?
P1 C1 N1 C3 -5.8(8) . . . . ?
N1 C1 N2 C11 -0.1(6) . . . . ?
P1 C1 N2 C11 -179.1(4) . . . . ?
N1 C1 N2 C7 175.3(5) . . . . ?
P1 C1 N2 C7 -3.7(8) . . . . ?
C13 C2 C3 C4 3.4(8) . . . . ?
C16 C2 C3 C4 -173.9(5) . . . . ?
C13 C2 C3 N1 179.8(5) . . . . ?
C16 C2 C3 N1 2.6(8) . . . . ?
C1 N1 C3 C4 -100.9(7) . . . . ?
C10 N1 C3 C4 73.2(7) . . . . ?
C1 N1 C3 C2 82.4(7) . . . . ?
C10 N1 C3 C2 -103.5(6) . . . . ?
C2 C3 C4 C12 -4.9(8) . . . . ?
N1 C3 C4 C12 178.6(5) . . . . ?
C2 C3 C4 C17 172.0(6) . . . . ?
N1 C3 C4 C17 -4.5(8) . . . . ?
C15 C6 C7 C8 -2.3(9) . . . . ?
C19 C6 C7 C8 176.1(6) . . . . ?
C15 C6 C7 N2 -178.6(5) . . . . ?
C19 C6 C7 N2 -0.2(9) . . . . ?
C1 N2 C7 C6 -104.1(7) . . . . ?
C11 N2 C7 C6 70.7(7) . . . . ?
C1 N2 C7 C8 79.4(7) . . . . ?
C11 N2 C7 C8 -105.7(6) . . . . ?
C6 C7 C8 C14 1.9(9) . . . . ?
N2 C7 C8 C14 178.1(5) . . . . ?
C6 C7 C8 C20 -173.5(6) . . . . ?
N2 C7 C8 C20 2.7(8) . . . . ?
C1 N1 C10 C11 -0.7(6) . . . . ?
C3 N1 C10 C11 -175.7(5) . . . . ?
N1 C10 C11 N2 0.6(6) . . . . ?
C1 N2 C11 C10 -0.3(6) . . . . ?
C7 N2 C11 C10 -176.1(5) . . . . ?
C3 C4 C12 C5 3.1(9) . . . . ?
C17 C4 C12 C5 -173.9(5) . . . . ?
C13 C5 C12 C4 0.1(9) . . . . ?
C18 C5 C12 C4 -179.1(6) . . . . ?
C12 C5 C13 C2 -1.8(9) . . . . ?
C18 C5 C13 C2 177.5(5) . . . . ?
C3 C2 C13 C5 0.1(9) . . . . ?
C16 C2 C13 C5 177.4(5) . . . . ?
C15 C9 C14 C8 -0.8(9) . . . . ?
C21 C9 C14 C8 -179.9(6) . . . . ?
C7 C8 C14 C9 -0.3(9) . . . . ?
C20 C8 C14 C9 175.2(6) . . . . ?
C14 C9 C15 C6 0.3(9) . . . . ?
C21 C9 C15 C6 179.4(6) . . . . ?
C7 C6 C15 C9 1.2(9) . . . . ?
C19 C6 C15 C9 -177.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 I1 0.95 3.05 3.973(6) 164.2 2_565
C11 H11 I2 0.95 3.29 4.162(5) 153.0 1_455

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_g442_sq
_database_code_depnum_ccdc_archive 'CCDC 1842623'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H37 I N2 P, I, C H2 Cl2'
_chemical_formula_sum            'C28 H39 Cl2 I2 N2 P'
_chemical_formula_weight         759.28

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.7558(6)
_cell_length_b                   18.7258(11)
_cell_length_c                   16.3345(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.309(3)
_cell_angle_gamma                90
_cell_volume                     3214.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    8165
_cell_measurement_theta_min      1.67
_cell_measurement_theta_max      30.57

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.282
_exptl_absorpt_coefficient_mu    2.192
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.577
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5176
_exptl_absorpt_correction_T_max  0.6761
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39444
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.677
_diffrn_reflns_theta_max         30.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9825
_reflns_number_gt                8159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
Refinement with the listed atoms show residual electron density due to
a heavily solvent CH2Cl2 with some traces of CHCl3 which could not be refined 
with split atoms. Therefore the option "SQUEEZE" of the program package PLATON
(Spek, A.L. (2009). Acta Cryst. D65, 148-155.) was used to create a hkl
file taking into account the residual electron density in the void areas.

Therefore the atoms list and unit card do not agree. Only one molecule
CH2Cl2 per asymmetric unit is included into the SFAC and UNIT card.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+3.5701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9825
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.16420(2) 0.16058(2) 0.33692(2) 0.02187(4) Uani 1 1 d . . . . .
I2 I 0.36652(2) 0.40112(2) 0.78182(2) 0.02533(4) Uani 1 1 d . . . . .
P1 P 0.38896(6) 0.20333(4) 0.37561(4) 0.02386(12) Uani 1 1 d D . . . .
H1P H 0.377(3) 0.2563(12) 0.3256(16) 0.036 Uiso 1 1 d D U . . .
C1 C 0.38293(18) 0.24950(10) 0.47247(11) 0.0123(3) Uani 1 1 d . . . . .
N1 N 0.36518(16) 0.31999(9) 0.48223(10) 0.0128(3) Uani 1 1 d . . . . .
N2 N 0.40112(16) 0.21976(9) 0.54938(10) 0.0128(3) Uani 1 1 d . . . . .
C2 C 0.4750(2) 0.39810(11) 0.40140(12) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.35913(19) 0.37306(10) 0.41678(11) 0.0139(4) Uani 1 1 d . . . . .
C4 C 0.2397(2) 0.39703(11) 0.37332(12) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.55963(19) 0.12439(11) 0.57409(12) 0.0154(4) Uani 1 1 d . . . . .
C6 C 0.43330(19) 0.14555(10) 0.56934(11) 0.0136(4) Uani 1 1 d . . . . .
C7 C 0.3384(2) 0.10030(11) 0.58581(12) 0.0161(4) Uani 1 1 d . . . . .
C8 C 0.3725(2) 0.33477(11) 0.56601(12) 0.0158(4) Uani 1 1 d . . . . .
H8 H 0.3637 0.3803 0.5898 0.019 Uiso 1 1 calc R U . . .
C9 C 0.39436(19) 0.27243(11) 0.60748(12) 0.0153(4) Uani 1 1 d . . . . .
H9 H 0.4035 0.2658 0.6661 0.018 Uiso 1 1 calc R U . . .
C10 C 0.2400(2) 0.44776(12) 0.31073(13) 0.0227(4) Uani 1 1 d . . . . .
H10 H 0.1613 0.4658 0.2799 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3523(2) 0.47221(13) 0.29275(14) 0.0258(5) Uani 1 1 d . . . . .
H11 H 0.3496 0.5062 0.2493 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4689(2) 0.44780(12) 0.33730(14) 0.0234(5) Uani 1 1 d . . . . .
H12 H 0.5452 0.4651 0.3240 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3750(2) 0.03016(12) 0.60929(13) 0.0202(4) Uani 1 1 d . . . . .
H13 H 0.3141 -0.0022 0.6224 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4981(2) 0.00758(12) 0.61359(13) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.5208 -0.0404 0.6290 0.026 Uiso 1 1 calc R U . . .
C15 C 0.5892(2) 0.05375(12) 0.59581(13) 0.0198(4) Uani 1 1 d . . . . .
H15 H 0.6733 0.0369 0.5985 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6035(2) 0.37433(12) 0.45189(13) 0.0200(4) Uani 1 1 d . . . . .
H16 H 0.5884 0.3422 0.4977 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1151(2) 0.37240(12) 0.39291(13) 0.0191(4) Uani 1 1 d . . . . .
H17 H 0.1324 0.3289 0.4290 0.023 Uiso 1 1 calc R U . . .
C18 C 0.2025(2) 0.12382(12) 0.58197(13) 0.0200(4) Uani 1 1 d . . . . .
H18 H 0.1881 0.1700 0.5506 0.024 Uiso 1 1 calc R U . . .
C19 C 0.6634(2) 0.17547(12) 0.56052(14) 0.0195(4) Uani 1 1 d . . . . .
H19 H 0.6205 0.2191 0.5326 0.023 Uiso 1 1 calc R U . . .
C20 C 0.6790(3) 0.33253(16) 0.39885(17) 0.0341(6) Uani 1 1 d . . . . .
H20A H 0.7610 0.3182 0.4337 0.051 Uiso 1 1 calc R U . . .
H20B H 0.6310 0.2899 0.3761 0.051 Uiso 1 1 calc R U . . .
H20C H 0.6933 0.3626 0.3526 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6807(3) 0.43839(16) 0.4924(2) 0.0428(7) Uani 1 1 d . . . . .
H21A H 0.7632 0.4220 0.5246 0.064 Uiso 1 1 calc R U . . .
H21B H 0.6941 0.4716 0.4486 0.064 Uiso 1 1 calc R U . . .
H21C H 0.6343 0.4627 0.5298 0.064 Uiso 1 1 calc R U . . .
C22 C 0.0167(2) 0.35297(15) 0.31403(16) 0.0305(5) Uani 1 1 d . . . . .
H22A H -0.0621 0.3374 0.3297 0.046 Uiso 1 1 calc R U . . .
H22B H -0.0008 0.3948 0.2774 0.046 Uiso 1 1 calc R U . . .
H22C H 0.0498 0.3142 0.2844 0.046 Uiso 1 1 calc R U . . .
C23 C 0.0625(3) 0.43047(14) 0.44233(18) 0.0325(6) Uani 1 1 d . . . . .
H23A H -0.0181 0.4143 0.4549 0.049 Uiso 1 1 calc R U . . .
H23B H 0.1238 0.4399 0.4948 0.049 Uiso 1 1 calc R U . . .
H23C H 0.0480 0.4743 0.4089 0.049 Uiso 1 1 calc R U . . .
C24 C 0.1062(2) 0.06880(14) 0.53615(16) 0.0296(5) Uani 1 1 d . . . . .
H24A H 0.0196 0.0857 0.5348 0.044 Uiso 1 1 calc R U . . .
H24B H 0.1180 0.0627 0.4787 0.044 Uiso 1 1 calc R U . . .
H24C H 0.1197 0.0230 0.5657 0.044 Uiso 1 1 calc R U . . .
C25 C 0.1806(2) 0.13614(15) 0.67048(15) 0.0286(5) Uani 1 1 d . . . . .
H25A H 0.0925 0.1513 0.6672 0.043 Uiso 1 1 calc R U . . .
H25B H 0.1966 0.0917 0.7026 0.043 Uiso 1 1 calc R U . . .
H25C H 0.2387 0.1733 0.6983 0.043 Uiso 1 1 calc R U . . .
C26 C 0.7447(3) 0.14516(17) 0.5041(2) 0.0452(8) Uani 1 1 d . . . . .
H26A H 0.8096 0.1802 0.4976 0.068 Uiso 1 1 calc R U . . .
H26B H 0.7862 0.1013 0.5290 0.068 Uiso 1 1 calc R U . . .
H26C H 0.6911 0.1343 0.4491 0.068 Uiso 1 1 calc R U . . .
C27 C 0.7448(3) 0.1986(2) 0.64441(19) 0.0575(10) Uani 1 1 d . . . . .
H27A H 0.6900 0.2180 0.6798 0.086 Uiso 1 1 calc R U . . .
H27B H 0.7916 0.1573 0.6722 0.086 Uiso 1 1 calc R U . . .
H27C H 0.8053 0.2353 0.6351 0.086 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 P1 2.4966(6) . ?
I1 I2 3.3418(3) 4_565 ?
P1 C1 1.8163(19) . ?
P1 H1P 1.274(17) . ?
C1 N1 1.348(2) . ?
C1 N2 1.350(2) . ?
N1 C8 1.382(2) . ?
N1 C3 1.451(2) . ?
N2 C9 1.381(2) . ?
N2 C6 1.452(2) . ?
C2 C12 1.392(3) . ?
C2 C3 1.403(3) . ?
C2 C16 1.518(3) . ?
C3 C4 1.402(3) . ?
C4 C10 1.396(3) . ?
C4 C17 1.515(3) . ?
C5 C15 1.389(3) . ?
C5 C6 1.402(3) . ?
C5 C19 1.521(3) . ?
C6 C7 1.397(3) . ?
C7 C13 1.401(3) . ?
C7 C18 1.515(3) . ?
C8 C9 1.345(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C20 1.524(3) . ?
C16 C21 1.526(3) . ?
C16 H16 1.0000 . ?
C17 C22 1.527(3) . ?
C17 C23 1.533(3) . ?
C17 H17 1.0000 . ?
C18 C25 1.531(3) . ?
C18 C24 1.537(3) . ?
C18 H18 1.0000 . ?
C19 C26 1.510(3) . ?
C19 C27 1.523(4) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
P1 I1 I2 178.129(15) . 4_565 ?
C1 P1 I1 99.25(7) . . ?
C1 P1 H1P 99.8(13) . . ?
I1 P1 H1P 97.2(13) . . ?
N1 C1 N2 106.86(16) . . ?
N1 C1 P1 126.97(14) . . ?
N2 C1 P1 126.11(15) . . ?
C1 N1 C8 109.49(16) . . ?
C1 N1 C3 124.67(16) . . ?
C8 N1 C3 125.21(17) . . ?
C1 N2 C9 109.05(16) . . ?
C1 N2 C6 125.73(16) . . ?
C9 N2 C6 125.03(16) . . ?
C12 C2 C3 117.18(19) . . ?
C12 C2 C16 119.74(19) . . ?
C3 C2 C16 123.07(18) . . ?
C4 C3 C2 123.71(18) . . ?
C4 C3 N1 118.98(18) . . ?
C2 C3 N1 117.31(17) . . ?
C10 C4 C3 116.3(2) . . ?
C10 C4 C17 120.14(19) . . ?
C3 C4 C17 123.49(18) . . ?
C15 C5 C6 116.75(19) . . ?
C15 C5 C19 120.05(19) . . ?
C6 C5 C19 123.14(18) . . ?
C7 C6 C5 123.91(18) . . ?
C7 C6 N2 118.34(18) . . ?
C5 C6 N2 117.70(17) . . ?
C6 C7 C13 116.55(19) . . ?
C6 C7 C18 123.67(19) . . ?
C13 C7 C18 119.76(19) . . ?
C9 C8 N1 106.97(17) . . ?
C9 C8 H8 126.5 . . ?
N1 C8 H8 126.5 . . ?
C8 C9 N2 107.63(17) . . ?
C8 C9 H9 126.2 . . ?
N2 C9 H9 126.2 . . ?
C11 C10 C4 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C4 C10 H10 119.3 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C2 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C2 C12 H12 119.7 . . ?
C14 C13 C7 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C7 C13 H13 119.6 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C5 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C5 C15 H15 119.5 . . ?
C2 C16 C20 112.05(18) . . ?
C2 C16 C21 110.7(2) . . ?
C20 C16 C21 110.1(2) . . ?
C2 C16 H16 107.9 . . ?
C20 C16 H16 107.9 . . ?
C21 C16 H16 107.9 . . ?
C4 C17 C22 112.32(19) . . ?
C4 C17 C23 109.77(18) . . ?
C22 C17 C23 110.2(2) . . ?
C4 C17 H17 108.1 . . ?
C22 C17 H17 108.1 . . ?
C23 C17 H17 108.1 . . ?
C7 C18 C25 110.23(17) . . ?
C7 C18 C24 111.7(2) . . ?
C25 C18 C24 109.74(19) . . ?
C7 C18 H18 108.4 . . ?
C25 C18 H18 108.4 . . ?
C24 C18 H18 108.4 . . ?
C26 C19 C5 113.02(19) . . ?
C26 C19 C27 111.0(2) . . ?
C5 C19 C27 110.27(19) . . ?
C26 C19 H19 107.4 . . ?
C5 C19 H19 107.4 . . ?
C27 C19 H19 107.4 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 C26 H26A 109.5 . . ?
C19 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C19 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C27 H27A 109.5 . . ?
C19 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C19 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 P1 C1 N1 -96.80(17) . . . . ?
I1 P1 C1 N2 86.33(17) . . . . ?
N2 C1 N1 C8 0.1(2) . . . . ?
P1 C1 N1 C8 -177.25(15) . . . . ?
N2 C1 N1 C3 171.40(17) . . . . ?
P1 C1 N1 C3 -6.0(3) . . . . ?
N1 C1 N2 C9 0.1(2) . . . . ?
P1 C1 N2 C9 177.48(15) . . . . ?
N1 C1 N2 C6 -175.13(17) . . . . ?
P1 C1 N2 C6 2.3(3) . . . . ?
C12 C2 C3 C4 -2.2(3) . . . . ?
C16 C2 C3 C4 176.87(19) . . . . ?
C12 C2 C3 N1 178.58(18) . . . . ?
C16 C2 C3 N1 -2.4(3) . . . . ?
C1 N1 C3 C4 99.2(2) . . . . ?
C8 N1 C3 C4 -90.8(2) . . . . ?
C1 N1 C3 C2 -81.5(2) . . . . ?
C8 N1 C3 C2 88.5(2) . . . . ?
C2 C3 C4 C10 1.1(3) . . . . ?
N1 C3 C4 C10 -179.62(18) . . . . ?
C2 C3 C4 C17 -177.02(19) . . . . ?
N1 C3 C4 C17 2.2(3) . . . . ?
C15 C5 C6 C7 0.7(3) . . . . ?
C19 C5 C6 C7 -176.59(18) . . . . ?
C15 C5 C6 N2 178.05(17) . . . . ?
C19 C5 C6 N2 0.8(3) . . . . ?
C1 N2 C6 C7 -105.1(2) . . . . ?
C9 N2 C6 C7 80.5(2) . . . . ?
C1 N2 C6 C5 77.4(2) . . . . ?
C9 N2 C6 C5 -97.1(2) . . . . ?
C5 C6 C7 C13 0.8(3) . . . . ?
N2 C6 C7 C13 -176.60(17) . . . . ?
C5 C6 C7 C18 178.94(18) . . . . ?
N2 C6 C7 C18 1.6(3) . . . . ?
C1 N1 C8 C9 -0.3(2) . . . . ?
C3 N1 C8 C9 -171.51(18) . . . . ?
N1 C8 C9 N2 0.3(2) . . . . ?
C1 N2 C9 C8 -0.3(2) . . . . ?
C6 N2 C9 C8 174.99(18) . . . . ?
C3 C4 C10 C11 0.5(3) . . . . ?
C17 C4 C10 C11 178.7(2) . . . . ?
C4 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C2 -0.1(4) . . . . ?
C3 C2 C12 C11 1.6(3) . . . . ?
C16 C2 C12 C11 -177.4(2) . . . . ?
C6 C7 C13 C14 -1.5(3) . . . . ?
C18 C7 C13 C14 -179.73(19) . . . . ?
C7 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C5 0.8(3) . . . . ?
C6 C5 C15 C14 -1.4(3) . . . . ?
C19 C5 C15 C14 175.89(19) . . . . ?
C12 C2 C16 C20 -66.2(3) . . . . ?
C3 C2 C16 C20 114.8(2) . . . . ?
C12 C2 C16 C21 57.2(3) . . . . ?
C3 C2 C16 C21 -121.9(2) . . . . ?
C10 C4 C17 C22 47.8(3) . . . . ?
C3 C4 C17 C22 -134.1(2) . . . . ?
C10 C4 C17 C23 -75.2(3) . . . . ?
C3 C4 C17 C23 102.9(2) . . . . ?
C6 C7 C18 C25 -102.2(2) . . . . ?
C13 C7 C18 C25 75.9(2) . . . . ?
C6 C7 C18 C24 135.6(2) . . . . ?
C13 C7 C18 C24 -46.3(3) . . . . ?
C15 C5 C19 C26 48.4(3) . . . . ?
C6 C5 C19 C26 -134.4(2) . . . . ?
C15 C5 C19 C27 -76.5(3) . . . . ?
C6 C5 C19 C27 100.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 I2 0.95 3.15 3.7512(19) 122.5 .
C9 H9 I2 0.95 3.24 3.7907(19) 119.2 .

_refine_diff_density_max         1.395
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.089



# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.009 0.648 0.351 124 50 CH2Cl2
2 0.009 0.352 0.649 124 49 CH2Cl2
3 0.509 0.148 0.149 124 49 CH2Cl2
4 0.491 -0.148 0.851 124 50 CH2Cl2
_platon_squeeze_details          ?


# start Validation Reply Form
_vrf_CHEMW03_g442_sq             
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Refinement with the listed atoms show residual electron
density due to a heavily solvent CH2Cl2 with some traces of CHCl3 which 
could not be refined with split atoms. Therefore the option "SQUEEZE" 
of the program package PLATON (Spek, A.L. (2009). Acta Cryst. 
D65, 148-155.) was used to create a hkl file taking into account the 
residual electron density in the void areas.
Therefore the atoms list and unit card do not agree. Only one molecule
CH2Cl2 per asymmetric unit is included into the SFAC and UNIT card.
;
_vrf_PLAT434_g442_sq             
;
PROBLEM: Short Inter HL..HL Contact I1     ..  I2      ..       3.34 Ang.  
RESPONSE: halogen---halogen (I---I) interaction 
;
# end Validation Reply Form

