#------------------------------------------------------------------------------
#$Date: 2017-08-06 00:33:20 +0300 (Sun, 06 Aug 2017) $
#$Revision: 199598 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/08/2020844.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_2020844
loop_
_publ_author_name
'Sabbaghi, Fahimeh'
'Pourayoubi, Mehrdad'
'Farhadipour, Abolghasem'
'Ghorbanian, Nazila'
'Andreev, Pavel V.'
_publ_section_title
;
 A novel tubular hydrogen-bond pattern in a new diazaphosphole oxide: a
 combination of X-ray crystallography and theoretical study of hydrogen
 bonds
;
_journal_coeditor_code           LY3049
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              508
_journal_page_last               516
_journal_paper_doi               10.1107/S205322961700794X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C12 H11 Cl N3 O P'
_chemical_formula_sum            'C12 H11 Cl N3 O P'
_chemical_formula_weight         279.67
_space_group_IT_number           158
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 3 -2"c'
_symmetry_space_group_name_H-M   'P 3 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   15.8635(2)
_cell_length_b                   15.8635(2)
_cell_length_c                   8.97540(10)
_cell_measurement_reflns_used    15343
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.833
_cell_measurement_theta_min      3.743
_cell_volume                     1956.06(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
enCIFer (Allen et al., 2004)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0302
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3 Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            44280
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         3.428
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Agilent, 2014), based on expressions derived by
Clark & Reid (1995)]
;
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3553
_exptl_crystal_size_mid          0.2183
_exptl_crystal_size_min          0.1454
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.366
_refine_ls_abs_structure_details
;
Flack x determined using 1807 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.004(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0687P)²+0.4018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                3841
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ly3049sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1956.06(5)
_cod_database_code               2020844
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.42038(19) 0.43506(18) 0.1857(3) 0.0301(5) Uani d 1
P P1 0.48648(5) 0.34701(4) 0.02975(7) 0.02636(14) Uani d 1
Cl Cl1 0.11062(8) -0.11481(9) 0.2729(2) 0.0943(5) Uani d 1
C C7 0.37777(19) 0.15395(19) 0.1049(3) 0.0303(5) Uani d 1
C C6 0.36447(18) 0.40615(18) 0.0542(3) 0.0293(5) Uani d 1
C C5 0.2988(2) 0.4369(2) 0.0244(4) 0.0387(6) Uani d 1
H H5 0.2618 0.4179 -0.0624 0.046 Uiso calc 1
N N2 0.46328(17) 0.23506(16) 0.0495(3) 0.0326(4) Uani d 1
H H2A 0.5089 0.2241 0.0227 0.039 Uiso calc 1
C C12 0.3605(2) 0.0616(2) 0.0674(3) 0.0388(6) Uani d 1
H H12 0.4050 0.0552 0.0081 0.047 Uiso calc 1
C C11 0.2780(3) -0.0208(2) 0.1174(4) 0.0487(8) Uani d 1
H H11 0.2667 -0.0823 0.0912 0.058 Uiso calc 1
C C3 0.3435(3) 0.5245(2) 0.2576(4) 0.0450(7) Uani d 1
H H3 0.3354 0.5642 0.3255 0.054 Uiso calc 1
N N3 0.38993(18) 0.34958(18) -0.0347(3) 0.0328(4) Uani d 1
H H3A 0.3589 0.3196 -0.1139 0.039 Uiso calc 1
C C8 0.3118(2) 0.1625(2) 0.1967(4) 0.0446(7) Uani d 1
H H8 0.3230 0.2237 0.2242 0.054 Uiso calc 1
C C9 0.2293(3) 0.0797(3) 0.2473(5) 0.0555(9) Uani d 1
H H9 0.1853 0.0855 0.3088 0.067 Uiso calc 1
C C2 0.4098(2) 0.4938(2) 0.2884(3) 0.0383(6) Uani d 1
H H2 0.4460 0.5123 0.3759 0.046 Uiso calc 1
O O1 0.57753(15) 0.39939(15) -0.0583(2) 0.0358(4) Uani d 1
C C4 0.2892(3) 0.4970(2) 0.1274(4) 0.0459(7) Uani d 1
H H4 0.2458 0.5190 0.1088 0.055 Uiso calc 1
N N1 0.48379(18) 0.39743(18) 0.1895(2) 0.0330(4) Uani d 1
H H1A 0.5175 0.4003 0.2664 0.040 Uiso calc 1
C C10 0.2125(2) -0.0110(3) 0.2063(5) 0.0500(8) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.102 0.094 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.148 0.159 '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_publ_flag
C2 C1 N1 128.8(3) y
C2 C1 C6 120.7(3) ?
N1 C1 C6 110.5(2) y
O1 P1 N2 107.09(12) y
O1 P1 N1 116.40(13) y
N2 P1 N1 112.70(13) y
O1 P1 N3 116.94(12) y
N2 P1 N3 110.86(13) y
N1 P1 N3 92.48(12) y
C12 C7 C8 119.0(3) ?
C12 C7 N2 117.9(2) y
C8 C7 N2 123.1(2) y
C5 C6 N3 128.8(3) y
C5 C6 C1 120.7(3) ?
N3 C6 C1 110.4(2) y
C6 C5 C4 118.3(3) ?
C6 C5 H5 120.8 ?
C4 C5 H5 120.8 ?
C7 N2 P1 128.32(18) y
C7 N2 H2A 115.8 ?
P1 N2 H2A 115.8 ?
C11 C12 C7 120.8(3) ?
C11 C12 H12 119.6 ?
C7 C12 H12 119.6 ?
C10 C11 C12 119.4(3) ?
C10 C11 H11 120.3 ?
C12 C11 H11 120.3 ?
C4 C3 C2 121.1(3) ?
C4 C3 H3 119.4 ?
C2 C3 H3 119.4 ?
C6 N3 P1 112.48(18) y
C6 N3 H3A 123.8 ?
P1 N3 H3A 123.8 ?
C9 C8 C7 120.1(3) ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
C10 C9 C8 120.0(3) ?
C10 C9 H9 120.0 ?
C8 C9 H9 120.0 ?
C1 C2 C3 118.3(3) ?
C1 C2 H2 120.9 ?
C3 C2 H2 120.9 ?
C3 C4 C5 120.9(3) ?
C3 C4 H4 119.6 ?
C5 C4 H4 119.6 ?
C1 N1 P1 112.45(18) y
C1 N1 H1A 123.8 ?
P1 N1 H1A 123.8 ?
C9 C10 C11 120.6(3) ?
C9 C10 Cl1 120.0(3) ?
C11 C10 Cl1 119.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.380(4) ?
C1 N1 1.404(3) y
C1 C6 1.408(3) ?
P1 O1 1.484(2) y
P1 N2 1.633(2) y
P1 N1 1.653(2) y
P1 N3 1.657(2) y
Cl1 C10 1.738(3) ?
C7 C12 1.390(4) ?
C7 C8 1.391(4) ?
C7 N2 1.413(3) y
C6 C5 1.380(4) ?
C6 N3 1.403(3) y
C5 C4 1.390(5) ?
C5 H5 0.9300 ?
N2 H2A 0.8600 ?
C12 C11 1.383(5) ?
C12 H12 0.9300 ?
C11 C10 1.379(6) ?
C11 H11 0.9300 ?
C3 C4 1.387(5) ?
C3 C2 1.390(5) ?
C3 H3 0.9300 ?
N3 H3A 0.8600 ?
C8 C9 1.387(4) ?
C8 H8 0.9300 ?
C9 C10 1.376(6) ?
C9 H9 0.9300 ?
C2 H2 0.9300 ?
C4 H4 0.9300 ?
N1 H1A 0.8600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A O1 2_655 0.86 2.06 2.909(3) 170.7 y
N1 H1A O1 4_665 0.86 1.97 2.825(3) 173.7 y
N3 H3A Cg 6_554 0.86 2.46 3.303(3) 168.5 y

_cod_database_fobs_code 2020844
