#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:06:01 +0200 (Mon 06 de Jun de 2022) $
#$Revision: 275827 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/86/7158678.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_7158678
loop_
_publ_author_name
'Peng, Lingteng'
'Hu, Zhifang'
'Zhao, Yanting'
'Peng, Lifen'
'Xu, Zhi'
'Yin, Shuang-Feng'
'Tang, Zilong'
'Qiu, Renhua'
'Kambe, Nobuaki'
_publ_section_title
;
 One-pot synthesis of phosphorylnaphth[2,1-d]oxazoles and products
 as P,N-ligands in C-N and C-C formation.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4110
_journal_page_last               4114
_journal_paper_doi               10.1039/d2ob00565d
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C29 H20 N O3 P'
_chemical_formula_sum            'C29 H20 N O3 P'
_chemical_formula_weight         461.43
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-07 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                65.707(10)
_cell_angle_beta                 75.725(9)
_cell_angle_gamma                64.564(10)
_cell_formula_units_Z            2
_cell_length_a                   10.5429(11)
_cell_length_b                   10.9205(10)
_cell_length_c                   11.7539(12)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0810
_cell_measurement_theta_min      2.4480
_cell_volume                     1109.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  40.00   1.00    1.00    --   11.74 -57.00 -60.00  100
  2  ω    -21.00  88.00   1.00    1.00    --   11.74  77.00-150.00  109
  3  ω    -16.00  85.00   1.00    1.00    --   11.74  57.00  90.00  101
  4  ω     34.00  99.00   1.00    1.00    --   11.74-178.00 -60.00   65
  5  ω    -16.00   9.00   1.00    1.00    --   11.74  57.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482762000
_diffrn_orient_matrix_UB_12      -0.0259444000
_diffrn_orient_matrix_UB_13      -0.0061076000
_diffrn_orient_matrix_UB_21      0.0112907000
_diffrn_orient_matrix_UB_22      0.0287571000
_diffrn_orient_matrix_UB_23      -0.0661651000
_diffrn_orient_matrix_UB_31      0.0559678000
_diffrn_orient_matrix_UB_32      -0.0662619000
_diffrn_orient_matrix_UB_33      0.0005431000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10135
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.147
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0408
_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)+(0.0415P)²+0.4707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3375
_reflns_number_total             3901
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00565d2.cif
_cod_data_source_block           hddx1205
_cod_depositor_comments          'Adding full bibliography for 7158678.cif.'
_cod_database_code               7158678
_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.
;
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C28(H28), C19(H19), C6(H6), C25(H25), C27(H27), C26(H26), C2(H2A),
 C17(H17), C4(H4), C14(H14), C5(H5), C16(H16), C23(H23), C15(H15), C20(H20),
 C3(H3), C21(H21), C22(H22)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_data_collection 2018-12-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.632
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
P1 P 0.17823(5) 0.23297(5) 0.28763(4) 0.01840(14) Uani 1 1 d . . . . .
O1 O 0.51668(12) 0.47694(13) 0.21385(12) 0.0208(3) Uani 1 1 d . . . . .
O2 O 0.39453(13) 0.10569(14) 0.09947(13) 0.0276(3) Uani 1 1 d . . . . .
H2 H 0.317538 0.102816 0.133761 0.041 Uiso 1 1 calc GR . . . .
O3 O 0.15516(13) 0.14472(13) 0.23102(12) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.32558(14) 0.42771(15) 0.32188(14) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.40537(17) 0.49920(18) 0.30247(17) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.55227(18) 0.21958(19) 0.06824(16) 0.0206(4) Uani 1 1 d . . . . .
C13 C 0.34037(17) 0.25911(18) 0.21765(16) 0.0176(4) Uani 1 1 d . . . . .
C24 C 0.18555(17) 0.14895(18) 0.45417(17) 0.0181(4) Uani 1 1 d . . . . .
C12 C 0.42460(18) 0.19532(18) 0.13115(17) 0.0201(4) Uani 1 1 d . . . . .
C9 C 0.50306(18) 0.38009(18) 0.17571(17) 0.0186(4) Uani 1 1 d . . . . .
C18 C 0.03703(17) 0.40791(19) 0.25920(17) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.59237(18) 0.31723(18) 0.08863(17) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.38604(17) 0.35206(18) 0.24013(17) 0.0183(4) Uani 1 1 d . . . . .
C29 C 0.30030(18) 0.11082(18) 0.51611(17) 0.0207(4) Uani 1 1 d . . . . .
H29 H 0.377286 0.135386 0.471935 0.025 Uiso 1 1 calc R . . . .
C1 C 0.39011(18) 0.59535(18) 0.36487(17) 0.0207(4) Uani 1 1 d . . . . .
C28 C 0.29996(19) 0.03610(19) 0.64384(18) 0.0235(4) Uani 1 1 d . . . . .
H28 H 0.377241 0.009904 0.685357 0.028 Uiso 1 1 calc R . . . .
C19 C 0.00963(18) 0.4935(2) 0.32894(18) 0.0243(4) Uani 1 1 d . . . . .
H19 H 0.062375 0.459573 0.395910 0.029 Uiso 1 1 calc R . . . .
C6 C 0.30343(18) 0.5900(2) 0.47554(18) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.254045 0.528199 0.506409 0.029 Uiso 1 1 calc R . . . .
C25 C 0.07043(18) 0.11204(19) 0.52180(18) 0.0239(4) Uani 1 1 d . . . . .
H25 H -0.006912 0.137928 0.480488 0.029 Uiso 1 1 calc R . . . .
C27 C 0.18515(19) -0.00004(19) 0.71044(18) 0.0253(4) Uani 1 1 d . . . . .
H27 H 0.185418 -0.049669 0.796440 0.030 Uiso 1 1 calc R . . . .
C26 C 0.07015(19) 0.0376(2) 0.64923(18) 0.0267(4) Uani 1 1 d . . . . .
H26 H -0.006678 0.012876 0.693656 0.032 Uiso 1 1 calc R . . . .
C2 C 0.4613(2) 0.6902(2) 0.31850(19) 0.0264(4) Uani 1 1 d . . . . .
H2A H 0.519609 0.694505 0.244454 0.032 Uiso 1 1 calc R . . . .
C17 C 0.71602(19) 0.3417(2) 0.02398(17) 0.0254(4) Uani 1 1 d . . . . .
H17 H 0.741463 0.407233 0.035447 0.030 Uiso 1 1 calc R . . . .
C4 C 0.3611(2) 0.7702(2) 0.4930(2) 0.0300(5) Uani 1 1 d . . . . .
H4 H 0.351752 0.828643 0.536362 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6404(2) 0.1466(2) -0.01343(18) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.616539 0.081200 -0.026878 0.032 Uiso 1 1 calc R . . . .
C5 C 0.29073(19) 0.6760(2) 0.53937(19) 0.0278(5) Uani 1 1 d . . . . .
H5 H 0.234227 0.670745 0.614425 0.033 Uiso 1 1 calc R . . . .
C16 C 0.7984(2) 0.2694(2) -0.05531(19) 0.0312(5) Uani 1 1 d . . . . .
H16 H 0.879840 0.285833 -0.097534 0.037 Uiso 1 1 calc R . . . .
C23 C -0.0441(2) 0.4584(2) 0.16086(19) 0.0300(5) Uani 1 1 d . . . . .
H23 H -0.027326 0.400934 0.114255 0.036 Uiso 1 1 calc R . . . .
C15 C 0.7609(2) 0.1707(2) -0.07344(19) 0.0319(5) Uani 1 1 d . . . . .
H15 H 0.818458 0.121020 -0.126765 0.038 Uiso 1 1 calc R . . . .
C20 C -0.09629(19) 0.6299(2) 0.2993(2) 0.0306(5) Uani 1 1 d . . . . .
H20 H -0.114255 0.687330 0.346203 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4452(2) 0.7774(2) 0.3824(2) 0.0326(5) Uani 1 1 d . . . . .
H3 H 0.491615 0.841881 0.350545 0.039 Uiso 1 1 calc R . . . .
C21 C -0.1749(2) 0.6804(2) 0.2005(2) 0.0367(5) Uani 1 1 d . . . . .
H21 H -0.244788 0.772520 0.179805 0.044 Uiso 1 1 calc R . . . .
C22 C -0.1500(2) 0.5945(2) 0.1324(2) 0.0394(6) Uani 1 1 d . . . . .
H22 H -0.204705 0.628063 0.066880 0.047 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'
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
O3 P1 C13 108.80(8) . . ?
O3 P1 C24 112.53(8) . . ?
O3 P1 C18 110.97(8) . . ?
C13 P1 C18 108.56(8) . . ?
C24 P1 C13 109.16(8) . . ?
C24 P1 C18 106.75(9) . . ?
C7 O1 C9 103.57(13) . . ?
C7 N1 C8 104.19(15) . . ?
O1 C7 C1 117.98(15) . . ?
N1 C7 O1 114.74(16) . . ?
N1 C7 C1 127.27(17) . . ?
C10 C11 C12 120.56(17) . . ?
C14 C11 C12 120.98(17) . . ?
C14 C11 C10 118.46(17) . . ?
C12 C13 P1 120.55(13) . . ?
C12 C13 C8 116.10(16) . . ?
C8 C13 P1 123.22(14) . . ?
C29 C24 P1 124.23(14) . . ?
C29 C24 C25 119.49(17) . . ?
C25 C24 P1 116.12(13) . . ?
O2 C12 C11 114.93(16) . . ?
O2 C12 C13 122.91(16) . . ?
C13 C12 C11 122.16(16) . . ?
O1 C9 C10 127.43(15) . . ?
C8 C9 O1 107.91(16) . . ?
C8 C9 C10 124.65(17) . . ?
C19 C18 P1 122.66(13) . . ?
C19 C18 C23 119.51(17) . . ?
C23 C18 P1 117.81(15) . . ?
C9 C10 C11 115.03(16) . . ?
C9 C10 C17 125.39(17) . . ?
C17 C10 C11 119.57(18) . . ?
N1 C8 C13 129.04(16) . . ?
C9 C8 N1 109.58(15) . . ?
C9 C8 C13 121.37(17) . . ?
C28 C29 C24 119.75(17) . . ?
C6 C1 C7 118.48(16) . . ?
C6 C1 C2 119.48(18) . . ?
C2 C1 C7 122.03(17) . . ?
C29 C28 C27 120.44(16) . . ?
C18 C19 C20 120.15(18) . . ?
C5 C6 C1 119.89(18) . . ?
C26 C25 C24 120.71(16) . . ?
C26 C27 C28 120.15(17) . . ?
C25 C26 C27 119.45(17) . . ?
C3 C2 C1 119.78(19) . . ?
C16 C17 C10 120.21(19) . . ?
C3 C4 C5 119.68(19) . . ?
C15 C14 C11 120.73(19) . . ?
C6 C5 C4 120.50(19) . . ?
C17 C16 C15 120.36(19) . . ?
C22 C23 C18 119.8(2) . . ?
C14 C15 C16 120.6(2) . . ?
C21 C20 C19 120.1(2) . . ?
C4 C3 C2 120.64(19) . . ?
C22 C21 C20 119.98(18) . . ?
C21 C22 C23 120.38(19) . . ?
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
P1 O3 1.4965(13) . ?
P1 C13 1.7924(17) . ?
P1 C24 1.7932(18) . ?
P1 C18 1.8040(18) . ?
O1 C7 1.372(2) . ?
O1 C9 1.376(2) . ?
O2 C12 1.350(2) . ?
N1 C7 1.301(2) . ?
N1 C8 1.382(2) . ?
C7 C1 1.448(3) . ?
C11 C12 1.443(3) . ?
C11 C10 1.421(3) . ?
C11 C14 1.405(3) . ?
C13 C12 1.383(3) . ?
C13 C8 1.427(2) . ?
C24 C29 1.385(2) . ?
C24 C25 1.396(2) . ?
C9 C10 1.398(3) . ?
C9 C8 1.365(2) . ?
C18 C19 1.383(3) . ?
C18 C23 1.389(3) . ?
C10 C17 1.411(3) . ?
C29 C28 1.383(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.390(2) . ?
C28 C27 1.387(3) . ?
C19 C20 1.387(3) . ?
C6 C5 1.374(3) . ?
C25 C26 1.379(3) . ?
C27 C26 1.384(3) . ?
C2 C3 1.374(3) . ?
C17 C16 1.365(3) . ?
C4 C5 1.378(3) . ?
C4 C3 1.375(3) . ?
C14 C15 1.369(3) . ?
C16 C15 1.400(3) . ?
C23 C22 1.385(3) . ?
C20 C21 1.376(3) . ?
C21 C22 1.375(3) . ?
