#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:42:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178439 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/60/4026029.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_4026029
loop_
_publ_author_name
'K. V. Sajna'
'Ramesh Kotikalapudi'
'Manab Chakravarty'
'N. N. Bhuvan Kumar'
'K. C. Kumara Swamy'
_publ_section_title
;
 Cycloaddition Reactions of Allenylphosphonates and Related Allenes with
 Dialkyl Acetylenedicarboxylates, 1,3-Diphenylisobenzofuran, and
 Anthracene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              920
_journal_page_last               938
_journal_paper_doi               10.1021/jo102240u
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C22 H23 O3 P'
_chemical_formula_weight         366.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.597(9)
_cell_length_b                   13.366(5)
_cell_length_c                   6.132(3)
_cell_measurement_reflns_used    5736
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      3.05
_cell_volume                     1934.0(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16892
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plates
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0366P)²+2.0657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                1718
_reflns_number_total             1782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102240u_si_002_14.cif
_cod_data_source_block           compd-64
_cod_database_code               4026029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.08858(4) 0.2500 0.59788(17) 0.0402(3) Uani 1 2 d S
O1 O 0.05067(9) 0.15750(18) 0.5377(4) 0.0605(7) Uani 1 1 d .
O2 O 0.10426(12) 0.2500 0.8275(5) 0.0633(10) Uani 1 2 d S
C1 C 0.02069(15) 0.1587(4) 0.3299(6) 0.0804(13) Uani 1 1 d .
H1A H -0.0030 0.0996 0.3199 0.096 Uiso 1 1 calc R
H1B H 0.0481 0.1559 0.2122 0.096 Uiso 1 1 calc R
C2 C -0.01557(19) 0.2500 0.3013(8) 0.0773(19) Uani 1 2 d S
C3 C -0.0371(3) 0.2500 0.0638(9) 0.142(4) Uani 1 2 d S
H3A H -0.0496 0.3160 0.0253 0.213 Uiso 0.50 1 calc PR
H3B H -0.0682 0.2040 0.0503 0.213 Uiso 0.50 1 calc PR
H3C H -0.0070 0.2299 -0.0320 0.213 Uiso 0.50 1 calc PR
C4 C -0.0652(2) 0.2500 0.4586(9) 0.114(3) Uani 1 2 d S
H4A H -0.0915 0.1983 0.4181 0.171 Uiso 0.50 1 calc PR
H4B H -0.0840 0.3137 0.4531 0.171 Uiso 0.50 1 calc PR
H4C H -0.0517 0.2380 0.6039 0.171 Uiso 0.50 1 calc PR
C5 C 0.14533(15) 0.2500 0.4075(6) 0.0390(9) Uani 1 2 d S
H5 H 0.1356 0.2500 0.2605 0.047 Uiso 1 2 calc SR
C6 C 0.20058(15) 0.2500 0.4551(6) 0.0313(8) Uani 1 2 d S
C7 C 0.22720(15) 0.2500 0.6804(6) 0.0347(9) Uani 1 2 d S
H7A H 0.2152 0.1912 0.7606 0.042 Uiso 0.50 1 calc PR
H7B H 0.2152 0.3088 0.7606 0.042 Uiso 0.50 1 calc PR
C8 C 0.24547(15) 0.2500 0.2760(6) 0.0350(9) Uani 1 2 d S
H8 H 0.2286 0.2500 0.1300 0.042 Uiso 1 2 calc SR
C9 C 0.28193(10) 0.1587(2) 0.3149(4) 0.0350(6) Uani 1 1 d .
C10 C 0.29159(12) 0.0816(2) 0.1700(5) 0.0447(7) Uani 1 1 d .
H10 H 0.2736 0.0808 0.0350 0.054 Uiso 1 1 calc R
C11 C 0.32826(14) 0.0057(2) 0.2276(6) 0.0574(9) Uani 1 1 d .
H11 H 0.3362 -0.0451 0.1285 0.069 Uiso 1 1 calc R
C12 C 0.35325(14) 0.0044(3) 0.4310(6) 0.0611(9) Uani 1 1 d .
H12 H 0.3772 -0.0480 0.4690 0.073 Uiso 1 1 calc R
C13 C 0.34306(12) 0.0803(2) 0.5786(5) 0.0500(8) Uani 1 1 d .
H13 H 0.3597 0.0786 0.7160 0.060 Uiso 1 1 calc R
C14 C 0.30774(10) 0.1591(2) 0.5207(4) 0.0371(6) Uani 1 1 d .
C15 C 0.29262(15) 0.2500 0.6560(6) 0.0336(9) Uani 1 2 d S
H15 H 0.3119 0.2500 0.7976 0.040 Uiso 1 2 calc SR
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'
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
O2 P1 O1 111.84(12) . .
O2 P1 O1 111.84(12) . 7_565
O1 P1 O1 103.89(18) . 7_565
O2 P1 C5 116.36(18) . .
O1 P1 C5 105.97(12) . .
O1 P1 C5 105.97(12) 7_565 .
C1 O1 P1 118.2(2) . .
O1 C1 C2 112.8(3) . .
O1 C1 H1A 109.0 . .
C2 C1 H1A 109.0 . .
O1 C1 H1B 109.0 . .
C2 C1 H1B 109.0 . .
H1A C1 H1B 107.8 . .
C1 C2 C1 108.8(4) . 7_565
C1 C2 C4 111.5(3) . .
C1 C2 C4 111.5(3) 7_565 .
C1 C2 C3 107.4(3) . .
C1 C2 C3 107.4(3) 7_565 .
C4 C2 C3 110.2(4) . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C6 C5 P1 126.3(3) . .
C6 C5 H5 116.9 . .
P1 C5 H5 116.9 . .
C5 C6 C7 127.1(3) . .
C5 C6 C8 121.3(3) . .
C7 C6 C8 111.6(3) . .
C6 C7 C15 108.9(3) . .
C6 C7 H7A 109.9 . .
C15 C7 H7A 109.9 . .
C6 C7 H7B 109.9 . .
C15 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
C9 C8 C9 107.6(3) . 7_565
C9 C8 C6 106.4(2) . .
C9 C8 C6 106.4(2) 7_565 .
C9 C8 H8 112.0 . .
C9 C8 H8 112.0 7_565 .
C6 C8 H8 112.0 . .
C10 C9 C14 120.7(3) . .
C10 C9 C8 126.5(3) . .
C14 C9 C8 112.7(3) . .
C11 C10 C9 119.2(3) . .
C11 C10 H10 120.4 . .
C9 C10 H10 120.4 . .
C10 C11 C12 120.6(3) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C11 C12 C13 120.6(3) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C12 C13 C14 119.6(3) . .
C12 C13 H13 120.2 . .
C14 C13 H13 120.2 . .
C13 C14 C9 119.2(3) . .
C13 C14 C15 127.6(3) . .
C9 C14 C15 113.2(2) . .
C14 C15 C14 106.7(3) . 7_565
C14 C15 C7 106.7(2) . .
C14 C15 C7 106.7(2) 7_565 .
C14 C15 H15 112.1 . .
C14 C15 H15 112.1 7_565 .
C7 C15 H15 112.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.456(3) .
P1 O1 1.570(2) .
P1 O1 1.570(2) 7_565
P1 C5 1.777(4) .
O1 C1 1.458(4) .
C1 C2 1.500(5) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C1 1.500(5) 7_565
C2 C4 1.518(7) .
C2 C3 1.543(7) .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 C6 1.336(5) .
C5 H5 0.9300 .
C6 C7 1.518(5) .
C6 C8 1.526(5) .
C7 C15 1.551(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.512(3) .
C8 C9 1.512(3) 7_565
C8 H8 0.9800 .
C9 C10 1.380(4) .
C9 C14 1.401(4) .
C10 C11 1.379(4) .
C10 H10 0.9300 .
C11 C12 1.380(5) .
C11 H11 0.9300 .
C12 C13 1.380(5) .
C12 H12 0.9300 .
C13 C14 1.390(4) .
C13 H13 0.9300 .
C14 C15 1.514(4) .
C15 C14 1.514(4) 7_565
C15 H15 0.9800 .
