#------------------------------------------------------------------------------
#$Date: 2022-03-16 04:56:31 +0200 (Wed, 16 Mar 2022) $
#$Revision: 273718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/89/2108934.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_2108934
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 Br N O3 P'
_chemical_formula_sum            'C18 H15 Br N O3 P'
_chemical_formula_weight         404.19
_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                107.9070(10)
_cell_angle_beta                 95.1590(10)
_cell_angle_gamma                118.0100(10)
_cell_formula_units_Z            2
_cell_length_a                   10.06390(10)
_cell_length_b                   10.23060(10)
_cell_length_c                   10.5227(2)
_cell_measurement_reflns_used    4357
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      2.39
_cell_volume                     874.05(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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       -14
_diffrn_reflns_number            11517
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         2.118
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0287
_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)+(0.0246P)²+0.5692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3938
_reflns_number_total             4499
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5064sup1.cif
_cod_data_source_block           3Br
_cod_database_code               2108934
_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   0.667
_shelx_estimated_absorpt_t_min   0.410
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C2(H2), C3(H3), C4(H4), C16(H16), C15(H15),
 C14(H14), C8(H8), C5(H5), C6(H6), C18(H18), C17(H17)
;
_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
Br1 Br 0.36775(2) 0.27440(2) 0.29064(2) 0.01957(6) Uani 1 1 d . . . . .
P1 P 1.03184(5) 0.91186(5) 0.29050(5) 0.01065(10) Uani 1 1 d . . . . .
O1 O 0.96490(15) 0.95082(15) 0.17457(13) 0.0142(3) Uani 1 1 d . . . . .
O2 O 1.10196(15) 0.82278(15) 0.19575(13) 0.0127(3) Uani 1 1 d . . . . .
O3 O 1.14302(14) 1.05231(15) 0.41817(13) 0.0135(3) Uani 1 1 d . . . . .
N1 N 0.88782(18) 0.78002(18) 0.32705(17) 0.0131(3) Uani 1 1 d . . . . .
C10 C 0.4950(2) 0.3241(2) 0.0669(2) 0.0183(4) Uani 1 1 d . . . . .
H10 H 0.406621 0.220285 0.010049 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6075(2) 0.4113(2) 0.0110(2) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.595484 0.366315 -0.085913 0.022 Uiso 1 1 calc R U . . .
C12 C 0.7377(2) 0.5629(2) 0.09304(19) 0.0159(4) Uani 1 1 d . . . . .
H12 H 0.813158 0.620985 0.052526 0.019 Uiso 1 1 calc R U . . .
C7 C 0.7563(2) 0.6288(2) 0.23543(18) 0.0122(3) Uani 1 1 d . . . . .
C1 C 0.8939(2) 1.0428(2) 0.19806(19) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.8494(2) 1.0836(2) 0.3176(2) 0.0189(4) Uani 1 1 d . . . . .
H2 H 0.867119 1.051270 0.389720 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7779(3) 1.1733(3) 0.3298(2) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.747575 1.203601 0.411581 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7507(3) 1.2185(3) 0.2241(2) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.701784 1.279591 0.233222 0.029 Uiso 1 1 calc R U . . .
C16 C 1.3482(2) 0.6506(2) 0.3576(2) 0.0204(4) Uani 1 1 d . . . . .
H16 H 1.404411 0.611560 0.394890 0.025 Uiso 1 1 calc R U . . .
C15 C 1.4272(2) 0.8065(2) 0.3628(2) 0.0205(4) Uani 1 1 d . . . . .
H15 H 1.537464 0.873156 0.402678 0.025 Uiso 1 1 calc R U . . .
C14 C 1.3458(2) 0.8658(2) 0.31012(19) 0.0174(4) Uani 1 1 d . . . . .
H14 H 1.399098 0.972344 0.313203 0.021 Uiso 1 1 calc R U . . .
C13 C 1.1850(2) 0.7652(2) 0.25305(18) 0.0133(3) Uani 1 1 d . . . . .
C9 C 0.5155(2) 0.3933(2) 0.2088(2) 0.0145(4) Uani 1 1 d . . . . .
C8 C 0.6439(2) 0.5436(2) 0.29398(19) 0.0140(4) Uani 1 1 d . . . . .
H8 H 0.655350 0.588016 0.390787 0.017 Uiso 1 1 calc R U . . .
C5 C 0.7950(2) 1.1746(3) 0.1049(2) 0.0217(4) Uani 1 1 d . . . . .
H5 H 0.775382 1.204786 0.031834 0.026 Uiso 1 1 calc R U . . .
C6 C 0.8678(2) 1.0867(2) 0.09145(19) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.899068 1.057211 0.010055 0.020 Uiso 1 1 calc R U . . .
C18 C 1.1047(2) 0.6093(2) 0.2453(2) 0.0203(4) Uani 1 1 d . . . . .
H18 H 0.994513 0.542270 0.204706 0.024 Uiso 1 1 calc R U . . .
C17 C 1.1881(3) 0.5521(3) 0.2982(2) 0.0233(4) Uani 1 1 d . . . . .
H17 H 1.134801 0.444865 0.293433 0.028 Uiso 1 1 calc R U . . .
H1 H 0.881(3) 0.816(3) 0.403(3) 0.023(6) 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'
Br Br -0.2901 2.4595 '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'
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 109.84(8) . . ?
O2 P1 O1 95.64(7) . . ?
O2 P1 N1 108.37(8) . . ?
O3 P1 O1 115.40(7) . . ?
O3 P1 O2 116.24(7) . . ?
O3 P1 N1 110.39(8) . . ?
C1 O1 P1 124.04(11) . . ?
C13 O2 P1 119.61(11) . . ?
P1 N1 H1 113.6(18) . . ?
C7 N1 P1 128.84(13) . . ?
C7 N1 H1 115.8(18) . . ?
C11 C10 H10 121.1 . . ?
C11 C10 C9 117.83(17) . . ?
C9 C10 H10 121.1 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.66(18) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C7 119.35(18) . . ?
C7 C12 H12 120.3 . . ?
C12 C7 N1 122.95(16) . . ?
C12 C7 C8 120.01(17) . . ?
C8 C7 N1 117.03(16) . . ?
C2 C1 O1 122.93(17) . . ?
C6 C1 O1 115.18(16) . . ?
C6 C1 C2 121.87(17) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.39(18) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.66(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.74(19) . . ?
C5 C4 H4 120.1 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C17 C16 C15 120.16(19) . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.44(19) . . ?
C14 C15 H15 119.8 . . ?
C15 C14 H14 120.9 . . ?
C13 C14 C15 118.16(18) . . ?
C13 C14 H14 120.9 . . ?
C14 C13 O2 118.59(16) . . ?
C18 C13 O2 119.09(16) . . ?
C18 C13 C14 122.27(18) . . ?
C10 C9 Br1 119.11(14) . . ?
C8 C9 Br1 118.64(14) . . ?
C8 C9 C10 122.18(17) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.97(17) . . ?
C9 C8 H8 120.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.46(19) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.87(18) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C13 C18 H18 120.7 . . ?
C13 C18 C17 118.69(18) . . ?
C17 C18 H18 120.7 . . ?
C16 C17 C18 120.26(19) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
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
Br1 C9 1.8994(18) . ?
P1 O1 1.5825(13) . ?
P1 O2 1.5793(13) . ?
P1 O3 1.4676(13) . ?
P1 N1 1.6282(16) . ?
O1 C1 1.406(2) . ?
O2 C13 1.414(2) . ?
N1 C7 1.416(2) . ?
N1 H1 0.80(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C10 C9 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C7 1.394(3) . ?
C7 C8 1.396(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.387(3) . ?
C16 C17 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.393(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.385(3) . ?
C13 C18 1.379(3) . ?
C9 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.391(3) . ?
C17 H17 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
Br1 C9 C8 C7 177.35(13) . . . . ?
P1 O1 C1 C2 -12.3(2) . . . . ?
P1 O1 C1 C6 169.28(13) . . . . ?
P1 O2 C13 C14 -91.04(18) . . . . ?
P1 O2 C13 C18 91.54(18) . . . . ?
P1 N1 C7 C12 5.4(3) . . . . ?
P1 N1 C7 C8 -175.83(14) . . . . ?
O1 P1 O2 C13 177.60(13) . . . . ?
O1 P1 N1 C7 51.57(18) . . . . ?
O1 C1 C2 C3 -179.11(18) . . . . ?
O1 C1 C6 C5 178.59(17) . . . . ?
O2 P1 O1 C1 -175.51(13) . . . . ?
O2 P1 N1 C7 -51.72(18) . . . . ?
O2 C13 C18 C17 178.07(17) . . . . ?
O3 P1 O1 C1 -52.92(16) . . . . ?
O3 P1 O2 C13 55.65(15) . . . . ?
O3 P1 N1 C7 179.93(15) . . . . ?
N1 P1 O1 C1 72.64(15) . . . . ?
N1 P1 O2 C13 -69.31(14) . . . . ?
N1 C7 C8 C9 -178.35(16) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C10 C9 C8 C7 0.3(3) . . . . ?
C11 C10 C9 Br1 -177.72(14) . . . . ?
C11 C10 C9 C8 -0.7(3) . . . . ?
C11 C12 C7 N1 177.93(17) . . . . ?
C11 C12 C7 C8 -0.8(3) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C15 C14 C13 O2 -178.26(16) . . . . ?
C15 C14 C13 C18 -0.9(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C13 C18 C17 C16 0.3(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C17 C16 C15 C14 0.8(3) . . . . ?

_cod_database_fobs_code 2108934
