#------------------------------------------------------------------------------
#$Date: 2022-06-16 00:55:07 +0300 (Thu, 16 Jun 2022) $
#$Revision: 276051 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/02/7130232.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_7130232
loop_
_publ_author_name
'Dettling, Lea'
'Papke, Martin'
'Sklorz, Julian'
'Buzsaki, Daniel'
'Kelemen, Zsolt'
'Weber, Manuela'
'Nyulaszi, Laszlo'
'Muller, Christian'
_publ_section_title
;
 A New Access to Diazaphospholes via Cycloaddition-Cycloreversion
 Reactions on Triazaphospholes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02269A
_journal_year                    2022
_chemical_formula_moiety         'C15 H5 F6 N2 O5 P W'
_chemical_formula_sum            'C15 H5 F6 N2 O5 P W'
_chemical_formula_weight         622.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.123(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6629(3)
_cell_length_b                   18.3901(8)
_cell_length_c                   15.6561(7)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.58
_cell_volume                     1888.50(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30420
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.557
_diffrn_reflns_theta_min         2.579
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.290
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1166 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.6495.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.188
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.4846
_refine_diff_density_max         0.569
_refine_diff_density_min         -1.704
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0127P)²+2.2436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0413
_refine_ls_wR_factor_ref         0.0422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5238
_reflns_number_total             5650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02269a2.cif
_cod_data_source_block           pap228_5
_cod_database_code               7130232
_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   0.885
_shelx_estimated_absorpt_t_min   0.314
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
W1 W 0.75158(2) 0.33702(2) 0.52660(2) 0.00971(3) Uani 1 1 d . . . . .
P1 P 0.59535(8) 0.23125(3) 0.45521(4) 0.01069(10) Uani 1 1 d . . . . .
F4 F 0.2163(2) 0.25207(8) 0.24012(9) 0.0257(3) Uani 1 1 d . . . . .
F5 F 0.0639(2) 0.24597(9) 0.35027(10) 0.0276(3) Uani 1 1 d . . . . .
F3 F 0.1059(2) 0.10642(9) 0.27129(10) 0.0242(3) Uani 1 1 d . . . . .
F1 F 0.3560(3) 0.10688(9) 0.20176(10) 0.0290(4) Uani 1 1 d . . . . .
F6 F 0.2914(3) 0.32789(8) 0.34619(12) 0.0323(4) Uani 1 1 d . . . . .
F2 F 0.3263(3) 0.02011(8) 0.29077(11) 0.0295(4) Uani 1 1 d . . . . .
O5 O 1.1933(2) 0.26420(9) 0.55395(11) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.3361(3) 0.42578(10) 0.51069(12) 0.0235(4) Uani 1 1 d . . . . .
O3 O 0.9698(3) 0.48110(9) 0.60623(13) 0.0261(4) Uani 1 1 d . . . . .
O4 O 0.6956(3) 0.27823(11) 0.71317(12) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.7767(3) 0.38791(10) 0.33352(12) 0.0272(4) Uani 1 1 d . . . . .
N1 N 0.5821(3) 0.09849(10) 0.39917(12) 0.0136(3) Uani 1 1 d . . . . .
N2 N 0.6825(3) 0.14554(10) 0.45900(12) 0.0120(3) Uani 1 1 d . . . . .
C13 C 0.8920(4) 0.42913(12) 0.57798(15) 0.0171(4) Uani 1 1 d . . . . .
C15 C 1.0339(3) 0.28876(12) 0.54323(14) 0.0131(4) Uani 1 1 d . . . . .
C12 C 0.4814(3) 0.39227(12) 0.51590(15) 0.0152(4) Uani 1 1 d . . . . .
C11 C 0.7737(3) 0.37110(12) 0.40340(15) 0.0157(4) Uani 1 1 d . . . . .
C8 C 0.4073(3) 0.20829(12) 0.37077(14) 0.0127(4) Uani 1 1 d . . . . .
C14 C 0.7163(3) 0.29968(12) 0.64725(15) 0.0161(4) Uani 1 1 d . . . . .
C7 C 0.4308(3) 0.13411(12) 0.35119(14) 0.0135(4) Uani 1 1 d . . . . .
C10 C 0.2451(4) 0.25803(13) 0.32697(15) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.3048(4) 0.09147(12) 0.27863(15) 0.0164(4) Uani 1 1 d . . . . .
C1 C 0.8585(3) 0.11871(11) 0.51734(14) 0.0121(4) Uani 1 1 d . . . . .
C6 C 0.8565(4) 0.11585(12) 0.60572(15) 0.0158(4) Uani 1 1 d . . . . .
H6 H 0.739088 0.130458 0.628051 0.019 Uiso 1 1 calc R . . . .
C5 C 1.0294(4) 0.09124(13) 0.66098(16) 0.0197(5) Uani 1 1 d . . . . .
H5 H 1.030692 0.089177 0.721704 0.024 Uiso 1 1 calc R . . . .
C4 C 1.1997(4) 0.06972(13) 0.62813(17) 0.0200(5) Uani 1 1 d . . . . .
H4 H 1.317713 0.053323 0.666395 0.024 Uiso 1 1 calc R . . . .
C3 C 1.1987(4) 0.07201(13) 0.53930(17) 0.0190(5) Uani 1 1 d . . . . .
H3 H 1.315417 0.056592 0.516991 0.023 Uiso 1 1 calc R . . . .
C2 C 1.0274(3) 0.09681(12) 0.48301(15) 0.0158(4) Uani 1 1 d . . . . .
H2 H 1.025952 0.098743 0.422266 0.019 Uiso 1 1 calc R . . . .
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'
F F 0.0171 0.0103 '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'
W W -0.8490 6.8722 '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
C13 W1 P1 175.27(7) . . ?
C13 W1 C15 87.84(9) . . ?
C13 W1 C12 87.47(9) . . ?
C13 W1 C11 90.76(9) . . ?
C13 W1 C14 91.93(9) . . ?
C15 W1 P1 91.23(6) . . ?
C15 W1 C11 92.04(9) . . ?
C15 W1 C14 89.39(9) . . ?
C12 W1 P1 93.51(6) . . ?
C12 W1 C15 175.24(9) . . ?
C12 W1 C11 88.79(9) . . ?
C12 W1 C14 90.01(9) . . ?
C11 W1 P1 84.64(6) . . ?
C11 W1 C14 177.00(9) . . ?
C14 W1 P1 92.69(7) . . ?
N2 P1 W1 128.98(7) . . ?
N2 P1 C8 89.85(10) . . ?
C8 P1 W1 139.81(8) . . ?
C7 N1 N2 108.03(18) . . ?
N1 N2 P1 116.62(15) . . ?
N1 N2 C1 117.70(17) . . ?
C1 N2 P1 125.62(15) . . ?
O3 C13 W1 179.4(2) . . ?
O5 C15 W1 177.54(19) . . ?
O2 C12 W1 176.9(2) . . ?
O1 C11 W1 176.3(2) . . ?
C7 C8 P1 108.21(16) . . ?
C7 C8 C10 126.4(2) . . ?
C10 C8 P1 125.43(16) . . ?
O4 C14 W1 179.0(2) . . ?
N1 C7 C8 117.3(2) . . ?
N1 C7 C9 116.03(19) . . ?
C8 C7 C9 126.7(2) . . ?
F4 C10 C8 112.28(19) . . ?
F5 C10 F4 106.66(19) . . ?
F5 C10 F6 106.3(2) . . ?
F5 C10 C8 112.9(2) . . ?
F6 C10 F4 106.9(2) . . ?
F6 C10 C8 111.42(19) . . ?
F3 C9 C7 111.68(18) . . ?
F1 C9 F3 106.53(19) . . ?
F1 C9 C7 111.80(18) . . ?
F2 C9 F3 107.16(19) . . ?
F2 C9 F1 107.42(19) . . ?
F2 C9 C7 111.9(2) . . ?
C6 C1 N2 119.73(19) . . ?
C6 C1 C2 121.7(2) . . ?
C2 C1 N2 118.6(2) . . ?
C1 C6 C5 118.8(2) . . ?
C4 C5 C6 120.4(2) . . ?
C5 C4 C3 120.2(2) . . ?
C4 C3 C2 120.2(2) . . ?
C1 C2 C3 118.7(2) . . ?
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
W1 P1 2.3891(6) . ?
W1 C13 2.032(2) . ?
W1 C15 2.055(2) . ?
W1 C12 2.048(2) . ?
W1 C11 2.058(2) . ?
W1 C14 2.062(2) . ?
P1 N2 1.6770(19) . ?
P1 C8 1.707(2) . ?
F4 C10 1.344(3) . ?
F5 C10 1.340(3) . ?
F3 C9 1.338(3) . ?
F1 C9 1.338(3) . ?
F6 C10 1.343(3) . ?
F2 C9 1.330(3) . ?
O5 C15 1.139(3) . ?
O2 C12 1.138(3) . ?
O3 C13 1.139(3) . ?
O4 C14 1.135(3) . ?
O1 C11 1.141(3) . ?
N1 N2 1.361(3) . ?
N1 C7 1.321(3) . ?
N2 C1 1.441(3) . ?
C8 C7 1.413(3) . ?
C8 C10 1.488(3) . ?
C7 C9 1.508(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.390(3) . ?
C6 C5 1.389(3) . ?
C5 C4 1.383(3) . ?
C4 C3 1.390(4) . ?
C3 C2 1.391(3) . ?
