#------------------------------------------------------------------------------
#$Date: 2022-03-16 04:56:31 +0200 (Wed, 16 Mar 2022) $
#$Revision: 273718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/89/2108941.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108941
loop_
_publ_author_name
'Hasija, Avantika'
'Som, Shubham'
'Chopra, Deepak'
_publ_section_title
;
 Investigation of crystal structures, energetics and isostructurality in
 halogen-substituted phosphoramidates
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622000889
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         'C18 H15 I N O3 P'
_chemical_formula_sum            'C18 H15 I N O3 P'
_chemical_formula_weight         451.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.2005(5)
_cell_length_b                   7.3428(2)
_cell_length_c                   19.8275(4)
_cell_measurement_reflns_used    8444
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.13
_cell_measurement_theta_min      2.90
_cell_volume                     3573.69(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18234
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.141
_diffrn_reflns_theta_min         1.659
_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.155
_refine_diff_density_max         1.375
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0241P)²+6.8304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4838
_reflns_number_total             5238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5064sup1.cif
_cod_data_source_block           4I
_cod_database_code               2108941
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.758
_shelx_estimated_absorpt_t_min   0.468
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 1.00937(2) 0.61390(2) 0.12487(2) 0.02255(5) Uani 1 1 d . . . . .
P1 P 0.80568(2) 0.00273(6) 0.23160(2) 0.01316(9) Uani 1 1 d . . . . .
O1 O 0.80484(6) -0.10972(17) 0.16330(7) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.86073(5) -0.08474(17) 0.27359(7) 0.0164(2) Uani 1 1 d . . . . .
O3 O 0.75805(5) -0.01587(18) 0.26200(7) 0.0176(3) Uani 1 1 d . . . . .
N1 N 0.81668(6) 0.2175(2) 0.21830(8) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.76438(8) -0.0763(2) 0.10274(10) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.71033(9) -0.1180(3) 0.10012(11) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.699472 -0.165993 0.139417 0.028 Uiso 1 1 calc R U . . .
C3 C 0.67237(9) -0.0876(3) 0.03822(12) 0.0283(5) Uani 1 1 d . . . . .
H3 H 0.634931 -0.112192 0.035491 0.034 Uiso 1 1 calc R U . . .
C4 C 0.68861(10) -0.0219(3) -0.01933(11) 0.0285(5) Uani 1 1 d . . . . .
H4 H 0.662390 -0.002406 -0.061366 0.034 Uiso 1 1 calc R U . . .
C5 C 0.74259(10) 0.0153(3) -0.01579(11) 0.0309(5) Uani 1 1 d . . . . .
H5 H 0.753629 0.059740 -0.055489 0.037 Uiso 1 1 calc R U . . .
C6 C 0.78121(9) -0.0119(3) 0.04582(11) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.818585 0.013640 0.048502 0.032 Uiso 1 1 calc R U . . .
C7 C 0.86109(7) 0.2994(2) 0.19806(9) 0.0137(3) Uani 1 1 d . . . . .
C8 C 0.89939(8) 0.2002(2) 0.17200(10) 0.0178(4) Uani 1 1 d . . . . .
H8 H 0.896205 0.071596 0.167773 0.021 Uiso 1 1 calc R U . . .
C9 C 0.94220(8) 0.2895(3) 0.15222(10) 0.0181(4) Uani 1 1 d . . . . .
H9 H 0.968290 0.221874 0.134705 0.022 Uiso 1 1 calc R U . . .
C10 C 0.94666(7) 0.4776(2) 0.15815(9) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.90919(8) 0.5770(3) 0.18477(10) 0.0178(3) Uani 1 1 d . . . . .
H11 H 0.912566 0.705520 0.189219 0.021 Uiso 1 1 calc R U . . .
C12 C 0.86688(7) 0.4875(2) 0.20478(9) 0.0156(3) Uani 1 1 d . . . . .
H12 H 0.841446 0.555500 0.223358 0.019 Uiso 1 1 calc R U . . .
C13 C 0.88008(7) -0.0487(3) 0.34466(10) 0.0160(3) Uani 1 1 d . . . . .
C14 C 0.91434(8) 0.0984(3) 0.36491(10) 0.0197(4) Uani 1 1 d . . . . .
H14 H 0.922499 0.180331 0.331568 0.024 Uiso 1 1 calc R U . . .
C15 C 0.93656(8) 0.1236(3) 0.43522(11) 0.0230(4) Uani 1 1 d . . . . .
H15 H 0.960095 0.223869 0.450259 0.028 Uiso 1 1 calc R U . . .
C16 C 0.92445(9) 0.0026(3) 0.48346(11) 0.0235(4) Uani 1 1 d . . . . .
H16 H 0.939895 0.020126 0.531362 0.028 Uiso 1 1 calc R U . . .
C17 C 0.89009(9) -0.1428(3) 0.46212(11) 0.0233(4) Uani 1 1 d . . . . .
H17 H 0.881952 -0.224866 0.495412 0.028 Uiso 1 1 calc R U . . .
C18 C 0.86721(8) -0.1700(3) 0.39183(11) 0.0209(4) Uani 1 1 d . . . . .
H18 H 0.843378 -0.269560 0.376801 0.025 Uiso 1 1 calc R U . . .
H1 H 0.7947(12) 0.285(4) 0.2249(14) 0.036(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 94.51(7) . . ?
O1 P1 N1 109.62(8) . . ?
O2 P1 N1 108.42(8) . . ?
O3 P1 O1 116.73(8) . . ?
O3 P1 O2 116.57(8) . . ?
O3 P1 N1 109.94(8) . . ?
C1 O1 P1 120.33(11) . . ?
C13 O2 P1 120.91(11) . . ?
P1 N1 H1 116(2) . . ?
C7 N1 P1 129.36(13) . . ?
C7 N1 H1 115(2) . . ?
C2 C1 O1 120.59(17) . . ?
C6 C1 O1 117.42(18) . . ?
C6 C1 C2 121.88(19) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.09(19) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 N1 122.91(16) . . ?
C12 C7 N1 118.02(15) . . ?
C12 C7 C8 119.07(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.18(16) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.82(17) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 I1 120.00(13) . . ?
C9 C10 C11 120.40(16) . . ?
C11 C10 I1 119.59(13) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.58(16) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.93(17) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 O2 119.26(17) . . ?
C18 C13 O2 118.36(17) . . ?
C18 C13 C14 122.22(18) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.50(18) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.23(19) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.28(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.38(19) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 118.40(19) . . ?
C13 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
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 C10 2.0992(17) . ?
P1 O1 1.5820(14) . ?
P1 O2 1.5834(14) . ?
P1 O3 1.4663(14) . ?
P1 N1 1.6326(16) . ?
O1 C1 1.410(2) . ?
O2 C13 1.408(2) . ?
N1 C7 1.407(2) . ?
N1 H1 0.78(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.376(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(2) . ?
C7 C12 1.393(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 C11 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 C18 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(3) . ?
C18 H18 0.9500 . ?
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 C10 C11 C12 178.07(14) . . . . ?
P1 O1 C1 C2 -67.3(2) . . . . ?
P1 O1 C1 C6 116.61(17) . . . . ?
P1 O2 C13 C14 -89.96(19) . . . . ?
P1 O2 C13 C18 94.67(18) . . . . ?
P1 N1 C7 C8 13.6(3) . . . . ?
P1 N1 C7 C12 -166.16(15) . . . . ?
O1 P1 O2 C13 -172.92(14) . . . . ?
O1 P1 N1 C7 -58.86(18) . . . . ?
O1 C1 C2 C3 -177.94(18) . . . . ?
O1 C1 C6 C5 177.29(19) . . . . ?
O2 P1 O1 C1 -175.21(13) . . . . ?
O2 P1 N1 C7 43.07(19) . . . . ?
O2 C13 C14 C15 -174.94(17) . . . . ?
O2 C13 C18 C17 174.74(17) . . . . ?
O3 P1 O1 C1 61.97(15) . . . . ?
O3 P1 O2 C13 -49.98(16) . . . . ?
O3 P1 N1 C7 171.56(16) . . . . ?
N1 P1 O1 C1 -63.82(15) . . . . ?
N1 P1 O2 C13 74.67(15) . . . . ?
N1 C7 C8 C9 179.39(18) . . . . ?
N1 C7 C12 C11 -178.96(17) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C6 C1 C2 C3 -2.0(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C8 C9 C10 I1 -177.66(14) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C12 C7 C8 C9 -0.9(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?

_cod_database_fobs_code 2108941
