#------------------------------------------------------------------------------
#$Date: 2022-02-01 00:50:47 +0200 (Tue, 01 Feb 2022) $
#$Revision: 272355 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129640.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_7129640
loop_
_publ_author_name
'Xie, Xiao-Yu'
'Xu, Yun-Fang'
'Li, Yang'
'Wang, Xiao-Dong'
'Zhu, Jie'
'Wu, Lei'
_publ_section_title
;
 Radical Modulated Regioselective Difunctionalization of Vinyl Enynes:
 Tunable Access to Naphthalen-1(2H)-ones and Allenic Alcohols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06994B
_journal_year                    2022
_chemical_formula_moiety         'C36 H26 Br O2 P'
_chemical_formula_sum            'C36 H26 Br O2 P'
_chemical_formula_weight         601.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-08-28 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.97(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.891(4)
_cell_length_b                   9.6242(19)
_cell_length_c                   29.836(12)
_cell_measurement_reflns_used    65371
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.440
_cell_measurement_theta_min      2.670
_cell_volume                     5681(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            65371
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_min         2.670
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0429
_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)+(0.0491P)²+4.6989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5007
_reflns_number_total             6418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06994b2.cif
_cod_data_source_block           T
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7129640
_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   0.849
_shelx_estimated_absorpt_t_max   0.900
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
Br1 Br 0.04260(2) 0.43635(2) 0.11056(2) 0.05038(10) Uani 1 1 d . . . . .
P1 P -0.13969(3) 0.62241(6) 0.12278(2) 0.03210(14) Uani 1 1 d . . . . .
O1 O -0.10525(9) 0.67327(19) 0.16643(5) 0.0437(4) Uani 1 1 d . . . . .
O2 O -0.08354(8) 0.91371(16) 0.09151(6) 0.0391(4) Uani 1 1 d . . . . .
C1 C -0.16578(12) 0.4424(2) 0.12712(8) 0.0348(5) Uani 1 1 d . . . . .
C2 C -0.13221(13) 0.3634(3) 0.16168(8) 0.0437(6) Uani 1 1 d . . . . .
H2A H -0.0984 0.4041 0.1813 0.052 Uiso 1 1 calc R U . . .
C3 C -0.14869(14) 0.2243(3) 0.16720(10) 0.0516(7) Uani 1 1 d . . . . .
H3A H -0.1263 0.1731 0.1906 0.062 Uiso 1 1 calc R U . . .
C4 C -0.19801(14) 0.1622(3) 0.13805(10) 0.0520(7) Uani 1 1 d . . . . .
H4A H -0.2082 0.0686 0.1413 0.062 Uiso 1 1 calc R U . . .
C5 C -0.23224(13) 0.2393(3) 0.10401(10) 0.0502(7) Uani 1 1 d . . . . .
H5A H -0.2658 0.1975 0.0845 0.060 Uiso 1 1 calc R U . . .
C6 C -0.21709(13) 0.3790(3) 0.09855(9) 0.0442(6) Uani 1 1 d . . . . .
H6A H -0.2411 0.4305 0.0759 0.053 Uiso 1 1 calc R U . . .
C7 C -0.21604(11) 0.7192(2) 0.10455(8) 0.0371(5) Uani 1 1 d . . . . .
C8 C -0.22766(14) 0.7922(3) 0.06441(10) 0.0560(7) Uani 1 1 d . . . . .
H8A H -0.1969 0.7864 0.0431 0.067 Uiso 1 1 calc R U . . .
C9 C -0.28537(17) 0.8744(4) 0.05591(12) 0.0708(9) Uani 1 1 d . . . . .
H9A H -0.2929 0.9229 0.0289 0.085 Uiso 1 1 calc R U . . .
C10 C -0.33089(15) 0.8840(4) 0.08711(15) 0.0736(11) Uani 1 1 d . . . . .
H10A H -0.3692 0.9392 0.0813 0.088 Uiso 1 1 calc R U . . .
C11 C -0.32008(16) 0.8125(4) 0.12683(15) 0.0748(10) Uani 1 1 d . . . . .
H11A H -0.3511 0.8193 0.1480 0.090 Uiso 1 1 calc R U . . .
C12 C -0.26284(15) 0.7295(3) 0.13570(11) 0.0585(8) Uani 1 1 d . . . . .
H12A H -0.2560 0.6807 0.1627 0.070 Uiso 1 1 calc R U . . .
C13 C 0.02156(11) 0.7428(2) 0.04930(7) 0.0307(5) Uani 1 1 d . . . . .
C14 C -0.01306(13) 0.8038(3) 0.01118(8) 0.0407(6) Uani 1 1 d . . . . .
H14A H -0.0592 0.8207 0.0105 0.049 Uiso 1 1 calc R U . . .
C15 C 0.02015(14) 0.8396(3) -0.02565(9) 0.0490(6) Uani 1 1 d . . . . .
H15A H -0.0041 0.8787 -0.0509 0.059 Uiso 1 1 calc R U . . .
C16 C 0.08840(14) 0.8181(3) -0.02537(9) 0.0491(6) Uani 1 1 d . . . . .
H16A H 0.1106 0.8424 -0.0502 0.059 Uiso 1 1 calc R U . . .
C17 C 0.12340(13) 0.7604(3) 0.01208(9) 0.0496(6) Uani 1 1 d . . . . .
H17A H 0.1697 0.7459 0.0126 0.060 Uiso 1 1 calc R U . . .
C18 C 0.09062(12) 0.7227(3) 0.04952(8) 0.0405(6) Uani 1 1 d . . . . .
H18A H 0.1152 0.6841 0.0747 0.049 Uiso 1 1 calc R U . . .
C19 C 0.10635(11) 0.5919(2) 0.19631(7) 0.0312(5) Uani 1 1 d . . . . .
C20 C 0.07674(14) 0.5031(3) 0.22509(8) 0.0421(6) Uani 1 1 d . . . . .
H20A H 0.0299 0.4986 0.2239 0.051 Uiso 1 1 calc R U . . .
C21 C 0.1162(2) 0.4206(3) 0.25575(9) 0.0626(9) Uani 1 1 d . . . . .
H21A H 0.0958 0.3606 0.2747 0.075 Uiso 1 1 calc R U . . .
C22 C 0.1851(2) 0.4282(3) 0.25789(11) 0.0745(11) Uani 1 1 d . . . . .
H22A H 0.2117 0.3727 0.2782 0.089 Uiso 1 1 calc R U . . .
C23 C 0.21538(17) 0.5174(4) 0.23017(11) 0.0714(10) Uani 1 1 d . . . . .
H23A H 0.2623 0.5226 0.2320 0.086 Uiso 1 1 calc R U . . .
C24 C 0.17625(13) 0.5999(3) 0.19928(9) 0.0507(7) Uani 1 1 d . . . . .
H24A H 0.1970 0.6604 0.1807 0.061 Uiso 1 1 calc R U . . .
C25 C 0.01033(11) 0.9138(2) 0.14681(7) 0.0291(4) Uani 1 1 d . . . . .
C26 C 0.00322(12) 1.0556(2) 0.15660(8) 0.0358(5) Uani 1 1 d . . . . .
H26A H -0.0266 1.1104 0.1381 0.043 Uiso 1 1 calc R U . . .
C27 C 0.04036(13) 1.1139(3) 0.19353(8) 0.0427(6) Uani 1 1 d . . . . .
H27A H 0.0359 1.2079 0.1998 0.051 Uiso 1 1 calc R U . . .
C28 C 0.08422(13) 1.0317(3) 0.22109(8) 0.0435(6) Uani 1 1 d . . . . .
H28A H 0.1088 1.0707 0.2462 0.052 Uiso 1 1 calc R U . . .
C29 C 0.09203(12) 0.8915(3) 0.21164(8) 0.0395(5) Uani 1 1 d . . . . .
H29A H 0.1217 0.8379 0.2306 0.047 Uiso 1 1 calc R U . . .
C30 C 0.05574(11) 0.8297(2) 0.17392(7) 0.0294(4) Uani 1 1 d . . . . .
C31 C -0.08287(11) 0.6280(2) 0.07845(7) 0.0302(5) Uani 1 1 d . . . . .
C32 C -0.09773(14) 0.5583(3) 0.04058(9) 0.0477(6) Uani 1 1 d . . . . .
H32A H -0.0669 0.5548 0.0192 0.057 Uiso 1 1 calc R U . . .
H32B H -0.1390 0.5126 0.0353 0.057 Uiso 1 1 calc R U . . .
C33 C -0.03458(11) 0.8525(2) 0.10930(7) 0.0283(4) Uani 1 1 d . . . . .
C34 C -0.01607(10) 0.7077(2) 0.09093(7) 0.0282(4) Uani 1 1 d . . . . .
C35 C 0.02973(11) 0.6277(2) 0.12586(7) 0.0297(4) Uani 1 1 d . . . . .
C36 C 0.06272(10) 0.6798(2) 0.16339(7) 0.0288(4) Uani 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'
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 C1 111.09(11) . . ?
O1 P1 C7 112.79(11) . . ?
C1 P1 C7 105.93(11) . . ?
O1 P1 C31 111.11(10) . . ?
C1 P1 C31 106.40(10) . . ?
C7 P1 C31 109.21(11) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 P1 117.02(18) . . ?
C6 C1 P1 124.58(19) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
C12 C7 C8 118.7(2) . . ?
C12 C7 P1 115.8(2) . . ?
C8 C7 P1 125.27(19) . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C18 C13 C14 117.8(2) . . ?
C18 C13 C34 121.70(19) . . ?
C14 C13 C34 120.34(19) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C20 C19 C24 118.9(2) . . ?
C20 C19 C36 119.9(2) . . ?
C24 C19 C36 121.2(2) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C19 C24 C23 119.9(3) . . ?
C19 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C30 C25 C26 120.8(2) . . ?
C30 C25 C33 120.50(19) . . ?
C26 C25 C33 118.5(2) . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
C26 C27 C28 119.6(2) . . ?
C26 C27 H27A 120.2 . . ?
C28 C27 H27A 120.2 . . ?
C27 C28 C29 120.7(2) . . ?
C27 C28 H28A 119.6 . . ?
C29 C28 H28A 119.6 . . ?
C28 C29 C30 121.0(2) . . ?
C28 C29 H29A 119.5 . . ?
C30 C29 H29A 119.5 . . ?
C25 C30 C29 117.6(2) . . ?
C25 C30 C36 120.41(19) . . ?
C29 C30 C36 121.9(2) . . ?
C32 C31 C34 124.6(2) . . ?
C32 C31 P1 120.24(18) . . ?
C34 C31 P1 114.90(14) . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
O2 C33 C25 122.14(19) . . ?
O2 C33 C34 119.32(19) . . ?
C25 C33 C34 118.47(18) . . ?
C35 C34 C31 110.64(17) . . ?
C35 C34 C13 110.75(17) . . ?
C31 C34 C13 112.89(17) . . ?
C35 C34 C33 111.05(17) . . ?
C31 C34 C33 107.48(17) . . ?
C13 C34 C33 103.80(16) . . ?
C36 C35 C34 126.32(19) . . ?
C36 C35 Br1 119.53(16) . . ?
C34 C35 Br1 114.07(14) . . ?
C35 C36 C30 119.53(19) . . ?
C35 C36 C19 122.51(19) . . ?
C30 C36 C19 117.96(18) . . ?
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 C35 1.921(2) . ?
P1 O1 1.4897(17) . ?
P1 C1 1.817(2) . ?
P1 C7 1.816(2) . ?
P1 C31 1.828(2) . ?
O2 C33 1.212(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.392(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C12 1.386(4) . ?
C7 C8 1.387(4) . ?
C8 C9 1.395(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.368(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.368(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.393(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C18 1.386(3) . ?
C13 C14 1.396(3) . ?
C13 C34 1.553(3) . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.398(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.386(3) . ?
C19 C24 1.386(3) . ?
C19 C36 1.502(3) . ?
C20 C21 1.390(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.369(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.392(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C30 1.405(3) . ?
C25 C26 1.406(3) . ?
C25 C33 1.480(3) . ?
C26 C27 1.380(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.383(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.391(3) . ?
C28 H28A 0.9300 . ?
C29 C30 1.404(3) . ?
C29 H29A 0.9300 . ?
C30 C36 1.486(3) . ?
C31 C32 1.321(3) . ?
C31 C34 1.546(3) . ?
C32 H32A 0.9300 . ?
C32 H32B 0.9300 . ?
C33 C34 1.556(3) . ?
C34 C35 1.520(3) . ?
C35 C36 1.335(3) . ?
