#------------------------------------------------------------------------------
#$Date: 2022-03-16 04:56:31 +0200 (Wed, 16 Mar 2022) $
#$Revision: 273718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/89/2108937.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_2108937
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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                109.0980(10)
_cell_angle_beta                 95.7340(10)
_cell_angle_gamma                116.9670(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0600(2)
_cell_length_b                   10.4577(2)
_cell_length_c                   10.6104(2)
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.35
_cell_volume                     898.35(3)
_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 0.969
_diffrn_measured_fraction_theta_max 0.941
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11038
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.126
_exptl_absorpt_coefficient_mu    1.886
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0141P)²+0.9249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3639
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5064sup1.cif
_cod_data_source_block           3I
_cod_database_code               2108937
_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   0.840
_shelx_estimated_absorpt_t_min   0.558
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), 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'
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 0.36293(2) 0.26885(2) 0.29159(2) 0.01635(7) Uani 1 1 d . . . . .
P1 P 1.02586(8) 0.90785(9) 0.28786(8) 0.01144(17) Uani 1 1 d . . . . .
O1 O 1.0962(2) 0.8191(2) 0.1927(2) 0.0124(4) Uani 1 1 d . . . . .
O2 O 0.9550(2) 0.9415(2) 0.1711(2) 0.0131(5) Uani 1 1 d . . . . .
O3 O 1.1373(2) 1.0480(2) 0.4158(2) 0.0135(5) Uani 1 1 d . . . . .
N1 N 0.8857(3) 0.7807(3) 0.3238(3) 0.0124(6) Uani 1 1 d . . . . .
H1 H 0.881(3) 0.815(4) 0.399(3) 0.015 Uiso 1 1 d . U . . .
C1 C 1.1818(3) 0.7645(3) 0.2509(3) 0.0137(7) Uani 1 1 d . . . . .
C2 C 1.1033(4) 0.6117(4) 0.2405(3) 0.0203(7) Uani 1 1 d . . . . .
H2 H 0.993658 0.545534 0.198265 0.024 Uiso 1 1 calc R U . . .
C3 C 1.1878(4) 0.5574(4) 0.2929(4) 0.0243(8) Uani 1 1 d . . . . .
H3 H 1.136056 0.452648 0.286524 0.029 Uiso 1 1 calc R U . . .
C4 C 1.3475(4) 0.6546(4) 0.3548(3) 0.0190(7) Uani 1 1 d . . . . .
H4 H 1.404848 0.617328 0.392179 0.023 Uiso 1 1 calc R U . . .
C5 C 1.4232(4) 0.8061(4) 0.3621(3) 0.0201(7) Uani 1 1 d . . . . .
H5 H 1.532933 0.872364 0.403670 0.024 Uiso 1 1 calc R U . . .
C6 C 1.3402(3) 0.8621(4) 0.3091(3) 0.0180(7) Uani 1 1 d . . . . .
H6 H 1.391953 0.965756 0.313096 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7565(3) 0.6302(3) 0.2319(3) 0.0114(6) Uani 1 1 d . . . . .
C8 C 0.6470(3) 0.5464(3) 0.2887(3) 0.0120(6) Uani 1 1 d . . . . .
H8 H 0.658593 0.591193 0.385658 0.014 Uiso 1 1 calc R U . . .
C9 C 0.5214(3) 0.3971(3) 0.2022(3) 0.0135(7) Uani 1 1 d . . . . .
C10 C 0.5013(3) 0.3280(3) 0.0609(3) 0.0158(7) Uani 1 1 d . . . . .
H10 H 0.415189 0.225000 0.003145 0.019 Uiso 1 1 calc R U . . .
C11 C 0.6103(3) 0.4132(3) 0.0059(3) 0.0165(7) Uani 1 1 d . . . . .
H11 H 0.598103 0.367683 -0.091131 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7366(3) 0.5631(3) 0.0891(3) 0.0156(7) Uani 1 1 d . . . . .
H12 H 0.809313 0.620082 0.049098 0.019 Uiso 1 1 calc R U . . .
C13 C 0.8878(3) 1.0368(3) 0.1966(3) 0.0131(7) Uani 1 1 d . . . . .
C14 C 0.8403(4) 1.0755(4) 0.3139(3) 0.0198(7) Uani 1 1 d . . . . .
H14 H 0.852878 1.039602 0.383235 0.024 Uiso 1 1 calc R U . . .
C15 C 0.7731(4) 1.1687(4) 0.3281(4) 0.0258(8) Uani 1 1 d . . . . .
H15 H 0.740118 1.197381 0.408237 0.031 Uiso 1 1 calc R U . . .
C16 C 0.7543(4) 1.2195(4) 0.2263(4) 0.0247(8) Uani 1 1 d . . . . .
H16 H 0.708524 1.282807 0.236495 0.030 Uiso 1 1 calc R U . . .
C17 C 0.8022(4) 1.1779(4) 0.1097(4) 0.0224(8) Uani 1 1 d . . . . .
H17 H 0.788418 1.212265 0.039477 0.027 Uiso 1 1 calc R U . . .
C18 C 0.8701(3) 1.0869(3) 0.0943(3) 0.0147(7) Uani 1 1 d . . . . .
H18 H 0.903981 1.059211 0.014562 0.018 Uiso 1 1 calc R U . . .
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 N1 108.31(12) . . ?
O2 P1 O1 95.44(11) . . ?
O2 P1 N1 109.77(12) . . ?
O3 P1 O1 116.13(11) . . ?
O3 P1 O2 115.46(11) . . ?
O3 P1 N1 110.70(12) . . ?
C1 O1 P1 119.34(18) . . ?
C13 O2 P1 123.55(18) . . ?
P1 N1 H1 114(2) . . ?
C7 N1 P1 129.0(2) . . ?
C7 N1 H1 116(2) . . ?
C2 C1 O1 118.8(3) . . ?
C6 C1 O1 118.9(3) . . ?
C6 C1 C2 122.2(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 N1 117.8(3) . . ?
C12 C7 N1 122.6(3) . . ?
C12 C7 C8 119.5(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 I1 118.6(2) . . ?
C10 C9 I1 119.4(2) . . ?
C10 C9 C8 121.9(3) . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C14 C13 O2 122.9(3) . . ?
C18 C13 O2 115.2(2) . . ?
C18 C13 C14 121.9(3) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.3(3) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 118.9(3) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
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 C9 2.106(3) . ?
P1 O1 1.5838(19) . ?
P1 O2 1.582(2) . ?
P1 O3 1.467(2) . ?
P1 N1 1.625(2) . ?
O1 C1 1.421(3) . ?
O2 C13 1.412(3) . ?
N1 H1 0.78(3) . ?
N1 C7 1.416(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.371(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C7 C12 1.394(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(4) . ?
C9 C10 1.381(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(4) . ?
C13 C18 1.380(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(4) . ?
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 C9 C10 C11 -177.9(2) . . . . ?
P1 O1 C1 C2 92.3(3) . . . . ?
P1 O1 C1 C6 -91.0(3) . . . . ?
P1 O2 C13 C14 -17.6(4) . . . . ?
P1 O2 C13 C18 163.6(2) . . . . ?
P1 N1 C7 C8 -176.8(2) . . . . ?
P1 N1 C7 C12 4.1(4) . . . . ?
O1 P1 O2 C13 -172.7(2) . . . . ?
O1 P1 N1 C7 -50.7(3) . . . . ?
O1 C1 C2 C3 177.8(3) . . . . ?
O1 C1 C6 C5 -178.2(3) . . . . ?
O2 P1 O1 C1 178.10(19) . . . . ?
O2 P1 N1 C7 52.4(3) . . . . ?
O2 C13 C14 C15 -179.1(3) . . . . ?
O2 C13 C18 C17 178.6(3) . . . . ?
O3 P1 O1 C1 56.3(2) . . . . ?
O3 P1 O2 C13 -50.3(2) . . . . ?
O3 P1 N1 C7 -179.0(2) . . . . ?
N1 P1 O1 C1 -69.0(2) . . . . ?
N1 P1 O2 C13 75.6(2) . . . . ?
N1 C7 C8 C9 -178.4(3) . . . . ?
N1 C7 C12 C11 177.8(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C6 C1 C2 C3 1.1(5) . . . . ?
C7 C8 C9 I1 177.4(2) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C7 0.8(4) . . . . ?
C12 C7 C8 C9 0.7(4) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C14 C13 C18 C17 -0.2(4) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C18 C13 C14 C15 -0.3(5) . . . . ?

_cod_database_fobs_code 2108937
