#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:14:37 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238115 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/47/1554779.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1554779
loop_
_publ_author_name
'Bard, Jeremy P.'
'Deng, Chun-Lin'
'Richardson, Hannah C.'
'Odulio, Jacob M.'
'Barker, Joshua E.'
'Zakharov, Lev N.'
'Cheong, Paul H.-Y.'
'Johnson, Darren W.'
'Haley, Michael M.'
_publ_section_title
;
 Synthesis, photophysical properties, and self-dimerization studies of
 2-λ5-phosphaquinolin-2-ones
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1257
_journal_paper_doi               10.1039/C9QO00199A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C22.5 H14.5 Cl1.5 F3 N2 O2 P'
_chemical_formula_weight         486.01
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-30 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.188(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.394(3)
_cell_length_b                   6.3419(5)
_cell_length_c                   28.119(3)
_cell_measurement_reflns_used    5952
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.09
_cell_measurement_theta_min      3.53
_cell_volume                     4484.2(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13891
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        66.972
_diffrn_reflns_theta_max         66.972
_diffrn_reflns_theta_min         3.515
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    3.161
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       cut-prizm
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0849
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1083P)²+19.0782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2236
_refine_ls_wR_factor_ref         0.2386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2947
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qo00199a2.cif
_cod_data_source_block           mhr257c_a
_cod_original_cell_volume        4484.3(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C22.50 H14.50 Cl1.50 F3 N2 O2 P'
_cod_database_code               1554779
_shelx_shelxl_version_number     2014/7
_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_min   0.648
_shelx_estimated_absorpt_t_max   0.884
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
P1 P 0.67320(4) 0.56095(19) 0.68135(4) 0.0425(4) Uani 1 1 d . . .
O1 O 0.70287(11) 0.7067(5) 0.72826(11) 0.0511(8) Uani 1 1 d . . .
O2 O 0.62906(11) 0.4369(5) 0.68703(11) 0.0525(9) Uani 1 1 d . . .
N1 N 0.71138(14) 0.3887(6) 0.67631(13) 0.0473(10) Uani 1 1 d D . .
N2 N 0.4663(2) 1.4974(9) 0.5611(2) 0.0843(16) Uani 1 1 d . . .
F1 F 0.6643(2) 0.1654(8) 0.43571(14) 0.1262(18) Uani 1 1 d . . .
F2 F 0.72987(18) -0.0215(8) 0.48243(17) 0.1136(15) Uani 1 1 d . . .
F3 F 0.6564(2) -0.1319(9) 0.46416(19) 0.146(2) Uani 1 1 d . . .
C1 C 0.63499(15) 0.6694(7) 0.61320(16) 0.0421(10) Uani 1 1 d . . .
C2 C 0.63944(16) 0.5790(7) 0.57235(16) 0.0423(10) Uani 1 1 d . . .
H2A H 0.6196 0.6429 0.5367 0.051 Uiso 1 1 calc R U .
C3 C 0.67040(16) 0.3984(7) 0.57621(16) 0.0408(10) Uani 1 1 d . . .
C4 C 0.70505(16) 0.3009(7) 0.62762(16) 0.0434(10) Uani 1 1 d . . .
C5 C 0.73298(18) 0.1208(8) 0.62941(18) 0.0511(12) Uani 1 1 d . . .
H5A H 0.7563 0.0549 0.6641 0.061 Uiso 1 1 calc R U .
C6 C 0.72711(19) 0.0382(9) 0.58173(19) 0.0563(12) Uani 1 1 d . . .
H6A H 0.7462 -0.0848 0.5832 0.068 Uiso 1 1 calc R U .
C7 C 0.69265(19) 0.1357(9) 0.53035(18) 0.0532(12) Uani 1 1 d . . .
C8 C 0.66562(18) 0.3121(8) 0.52807(18) 0.0498(11) Uani 1 1 d . . .
H8A H 0.6431 0.3783 0.4932 0.060 Uiso 1 1 calc R U .
C9 C 0.6856(3) 0.0359(11) 0.4788(2) 0.0733(17) Uani 1 1 d . . .
C10 C 0.59912(16) 0.8511(7) 0.60285(16) 0.0440(11) Uani 1 1 d . . .
C11 C 0.58735(19) 0.9919(8) 0.5607(2) 0.0542(12) Uani 1 1 d . . .
H11A H 0.6035 0.9745 0.5391 0.065 Uiso 1 1 calc R U .
C12 C 0.55266(19) 1.1578(8) 0.5490(2) 0.0582(14) Uani 1 1 d . . .
H12A H 0.5447 1.2513 0.5193 0.070 Uiso 1 1 calc R U .
C13 C 0.52989(17) 1.1875(8) 0.58023(19) 0.0546(13) Uani 1 1 d . . .
C14 C 0.5407(2) 1.0473(10) 0.6225(2) 0.0741(17) Uani 1 1 d . . .
H14A H 0.5244 1.0655 0.6439 0.089 Uiso 1 1 calc R U .
C15 C 0.5752(2) 0.8803(10) 0.6336(2) 0.0654(15) Uani 1 1 d . . .
H15A H 0.5825 0.7847 0.6627 0.079 Uiso 1 1 calc R U .
C16 C 0.4943(2) 1.3614(10) 0.5694(2) 0.0675(15) Uani 1 1 d . . .
C17 C 0.63836(18) 0.3644(9) 0.73857(18) 0.0529(12) Uani 1 1 d . . .
C18 C 0.6228(2) 0.4906(12) 0.7676(3) 0.0791(18) Uani 1 1 d . . .
H18A H 0.6074 0.6250 0.7536 0.095 Uiso 1 1 calc R U .
C19 C 0.6301(3) 0.4180(16) 0.8177(3) 0.104(3) Uani 1 1 d . . .
H19A H 0.6205 0.5039 0.8388 0.124 Uiso 1 1 calc R U .
C20 C 0.6513(3) 0.2218(16) 0.8366(3) 0.100(3) Uani 1 1 d . . .
H20A H 0.6546 0.1690 0.8698 0.120 Uiso 1 1 calc R U .
C21 C 0.6678(2) 0.1014(12) 0.8082(3) 0.083(2) Uani 1 1 d . . .
H21A H 0.6839 -0.0319 0.8226 0.099 Uiso 1 1 calc R U .
C22 C 0.6613(2) 0.1730(9) 0.7580(2) 0.0640(14) Uani 1 1 d . . .
H22A H 0.6727 0.0897 0.7380 0.077 Uiso 1 1 calc R U .
H1N H 0.7405(13) 0.321(7) 0.7095(13) 0.050(12) Uiso 1 1 d D . .
Cl1S Cl 0.4815(2) 0.7492(8) 0.6914(2) 0.238(2) Uani 1 1 d D . .
Cl2S Cl 0.5179(4) 1.1154(16) 0.7504(5) 0.247(5) Uani 0.5 1 d D . P
C1S C 0.4791(6) 0.895(2) 0.7424(7) 0.115(6) Uani 0.5 1 d D . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O1 P1 O2 110.83(19) . .
O1 P1 N1 112.67(18) . .
O2 P1 N1 108.2(2) . .
O1 P1 C1 118.2(2) . .
O2 P1 C1 101.87(17) . .
N1 P1 C1 104.2(2) . .
C17 O2 P1 122.1(3) . .
C4 N1 P1 127.3(3) . .
C4 N1 H1N 112(3) . .
P1 N1 H1N 121(3) . .
C2 C1 C10 122.3(4) . .
C2 C1 P1 117.8(3) . .
C10 C1 P1 119.9(3) . .
C1 C2 C3 127.8(4) . .
C1 C2 H2A 116.1 . .
C3 C2 H2A 116.1 . .
C8 C3 C4 118.6(4) . .
C8 C3 C2 119.9(4) . .
C4 C3 C2 121.5(4) . .
C5 C4 N1 120.9(4) . .
C5 C4 C3 119.8(4) . .
N1 C4 C3 119.3(4) . .
C6 C5 C4 120.5(4) . .
C6 C5 H5A 119.8 . .
C4 C5 H5A 119.8 . .
C5 C6 C7 119.9(5) . .
C5 C6 H6A 120.1 . .
C7 C6 H6A 120.1 . .
C8 C7 C6 120.3(4) . .
C8 C7 C9 121.4(5) . .
C6 C7 C9 118.3(5) . .
C7 C8 C3 121.0(4) . .
C7 C8 H8A 119.5 . .
C3 C8 H8A 119.5 . .
F3 C9 F2 105.4(6) . .
F3 C9 F1 107.4(6) . .
F2 C9 F1 102.9(5) . .
F3 C9 C7 113.2(5) . .
F2 C9 C7 114.3(5) . .
F1 C9 C7 112.9(5) . .
C11 C10 C15 118.0(5) . .
C11 C10 C1 120.5(4) . .
C15 C10 C1 121.4(4) . .
C10 C11 C12 121.5(5) . .
C10 C11 H11A 119.2 . .
C12 C11 H11A 119.2 . .
C13 C12 C11 120.1(5) . .
C13 C12 H12A 120.0 . .
C11 C12 H12A 120.0 . .
C12 C13 C14 119.6(5) . .
C12 C13 C16 120.9(5) . .
C14 C13 C16 119.5(5) . .
C13 C14 C15 119.9(5) . .
C13 C14 H14A 120.0 . .
C15 C14 H14A 120.0 . .
C10 C15 C14 120.8(5) . .
C10 C15 H15A 119.6 . .
C14 C15 H15A 119.6 . .
N2 C16 C13 179.5(7) . .
C22 C17 C18 121.8(5) . .
C22 C17 O2 119.9(5) . .
C18 C17 O2 118.3(5) . .
C17 C18 C19 118.9(7) . .
C17 C18 H18A 120.5 . .
C19 C18 H18A 120.5 . .
C20 C19 C18 119.7(7) . .
C20 C19 H19A 120.2 . .
C18 C19 H19A 120.2 . .
C21 C20 C19 120.7(6) . .
C21 C20 H20A 119.6 . .
C19 C20 H20A 119.6 . .
C20 C21 C22 120.4(6) . .
C20 C21 H21A 119.8 . .
C22 C21 H21A 119.8 . .
C17 C22 C21 118.4(6) . .
C17 C22 H22A 120.8 . .
C21 C22 H22A 120.8 . .
C1S Cl1S C1S 34.6(9) . 2_656
Cl2S Cl2S C1S 89.5(7) 2_656 2_656
Cl2S Cl2S C1S 54.0(6) 2_656 .
C1S Cl2S C1S 37.9(11) 2_656 .
C1S C1S Cl2S 88.2(8) 2_656 2_656
C1S C1S Cl1S 78.4(16) 2_656 .
Cl2S C1S Cl1S 128.2(13) 2_656 .
C1S C1S Cl2S 53.9(6) 2_656 .
Cl2S C1S Cl2S 36.5(7) 2_656 .
Cl1S C1S Cl2S 103.2(9) . .
C1S C1S Cl1S 67.0(15) 2_656 2_656
Cl2S C1S Cl1S 113.0(11) 2_656 2_656
Cl1S C1S Cl1S 107.1(9) . 2_656
Cl2S C1S Cl1S 104.1(9) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.471(3) .
P1 O2 1.594(3) .
P1 N1 1.624(4) .
P1 C1 1.783(4) .
O2 C17 1.406(5) .
N1 C4 1.398(5) .
N1 H1N 0.980(19) .
N2 C16 1.130(7) .
F1 C9 1.322(7) .
F2 C9 1.304(7) .
F3 C9 1.293(8) .
C1 C2 1.349(6) .
C1 C10 1.485(6) .
C2 C3 1.432(6) .
C2 H2A 0.9500 .
C3 C8 1.398(6) .
C3 C4 1.408(6) .
C4 C5 1.392(7) .
C5 C6 1.365(7) .
C5 H5A 0.9500 .
C6 C7 1.407(7) .
C6 H6A 0.9500 .
C7 C8 1.354(7) .
C7 C9 1.494(7) .
C8 H8A 0.9500 .
C10 C11 1.378(6) .
C10 C15 1.381(7) .
C11 C12 1.381(7) .
C11 H11A 0.9500 .
C12 C13 1.364(8) .
C12 H12A 0.9500 .
C13 C14 1.384(7) .
C13 C16 1.440(8) .
C14 C15 1.386(8) .
C14 H14A 0.9500 .
C15 H15A 0.9500 .
C17 C22 1.359(8) .
C17 C18 1.379(8) .
C18 C19 1.388(9) .
C18 H18A 0.9500 .
C19 C20 1.369(12) .
C19 H19A 0.9500 .
C20 C21 1.362(11) .
C20 H20A 0.9500 .
C21 C22 1.397(8) .
C21 H21A 0.9500 .
C22 H22A 0.9500 .
Cl1S C1S 1.737(15) .
Cl1S C1S 1.849(19) 2_656
Cl2S Cl2S 1.039(14) 2_656
Cl2S C1S 1.411(15) 2_656
Cl2S C1S 1.745(14) .
C1S C1S 1.07(3) 2_656
C1S Cl2S 1.411(15) 2_656
C1S Cl1S 1.849(19) 2_656
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
C22 H22A O1 0.95 2.65 3.463(7) 144.1 1_545
N1 H1N O1 0.980(19) 1.83(2) 2.807(4) 177(4) 4_646
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_4
O1 P1 O2 C17 -38.9(4) . .
N1 P1 O2 C17 85.0(4) . .
C1 P1 O2 C17 -165.5(4) . .
O1 P1 N1 C4 -146.4(4) . .
O2 P1 N1 C4 90.8(4) . .
C1 P1 N1 C4 -17.0(4) . .
O1 P1 C1 C2 133.5(3) . .
O2 P1 C1 C2 -104.9(4) . .
N1 P1 C1 C2 7.6(4) . .
O1 P1 C1 C10 -47.5(4) . .
O2 P1 C1 C10 74.1(3) . .
N1 P1 C1 C10 -173.4(3) . .
C10 C1 C2 C3 -176.8(4) . .
P1 C1 C2 C3 2.2(6) . .
C1 C2 C3 C8 172.8(4) . .
C1 C2 C3 C4 -5.7(7) . .
P1 N1 C4 C5 -164.7(4) . .
P1 N1 C4 C3 16.1(6) . .
C8 C3 C4 C5 -0.9(6) . .
C2 C3 C4 C5 177.6(4) . .
C8 C3 C4 N1 178.2(4) . .
C2 C3 C4 N1 -3.2(6) . .
N1 C4 C5 C6 -179.0(4) . .
C3 C4 C5 C6 0.1(7) . .
C4 C5 C6 C7 0.1(8) . .
C5 C6 C7 C8 0.6(8) . .
C5 C6 C7 C9 -177.6(5) . .
C6 C7 C8 C3 -1.4(7) . .
C9 C7 C8 C3 176.7(5) . .
C4 C3 C8 C7 1.6(7) . .
C2 C3 C8 C7 -177.0(4) . .
C8 C7 C9 F3 -103.6(7) . .
C6 C7 C9 F3 74.5(7) . .
C8 C7 C9 F2 135.8(6) . .
C6 C7 C9 F2 -46.1(8) . .
C8 C7 C9 F1 18.6(8) . .
C6 C7 C9 F1 -163.2(5) . .
C2 C1 C10 C11 -29.0(6) . .
P1 C1 C10 C11 152.1(3) . .
C2 C1 C10 C15 148.8(5) . .
P1 C1 C10 C15 -30.2(6) . .
C15 C10 C11 C12 -0.1(7) . .
C1 C10 C11 C12 177.7(4) . .
C10 C11 C12 C13 1.2(7) . .
C11 C12 C13 C14 -1.7(7) . .
C11 C12 C13 C16 178.9(4) . .
C12 C13 C14 C15 1.2(8) . .
C16 C13 C14 C15 -179.5(5) . .
C11 C10 C15 C14 -0.4(8) . .
C1 C10 C15 C14 -178.2(5) . .
C13 C14 C15 C10 -0.1(9) . .
P1 O2 C17 C22 -86.6(5) . .
P1 O2 C17 C18 94.4(5) . .
C22 C17 C18 C19 -1.1(9) . .
O2 C17 C18 C19 177.9(6) . .
C17 C18 C19 C20 -1.5(11) . .
C18 C19 C20 C21 3.4(11) . .
C19 C20 C21 C22 -2.7(11) . .
C18 C17 C22 C21 1.8(8) . .
O2 C17 C22 C21 -177.1(5) . .
C20 C21 C22 C17 0.1(9) . .
C1S Cl1S C1S Cl2S 78.4(14) 2_656 2_656
C1S Cl1S C1S Cl2S 48.3(9) 2_656 .
C1S Cl1S C1S Cl1S -61.3(11) 2_656 2_656
Cl2S Cl2S C1S C1S -157(3) 2_656 2_656
C1S Cl2S C1S Cl2S 157(3) 2_656 2_656
Cl2S Cl2S C1S Cl1S 138.5(18) 2_656 .
C1S Cl2S C1S Cl1S -64.8(17) 2_656 .
Cl2S Cl2S C1S Cl1S -109.7(17) 2_656 2_656
C1S Cl2S C1S Cl1S 47.0(17) 2_656 2_656
