#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024702.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_4024702
loop_
_publ_author_name
'N. N. Bhuvan Kumar'
'M. Nagarjuna Reddy'
'K. C. Kumara Swamy'
_publ_section_title
;
Reactivity of Allenylphosphonates toward Salicylaldehydes and Activated
Phenols: Facile Synthesis of Chromenes and Substituted Butadienes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5395
_journal_page_last               5404
_journal_paper_doi               10.1021/jo900896v
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C16 H21 O5 P'
_chemical_formula_weight         324.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 109.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.604(6)
_cell_length_b                   9.5310(19)
_cell_length_c                   11.840(2)
_cell_measurement_reflns_used    9306
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.25
_cell_volume                     3251.0(11)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15029
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.9401
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0823P)²+3.6187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                2500
_reflns_number_total             2858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900896v_si_002_03.cif
_cod_data_source_block           compd(E)-19
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024702
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.310070(19) 0.17747(6) 0.77667(5) 0.0418(2) Uani 1 1 d . . .
O1 O 0.33311(5) 0.02978(18) 0.77385(15) 0.0521(4) Uani 1 1 d . . .
O2 O 0.34781(5) 0.25465(17) 0.88360(15) 0.0491(4) Uani 1 1 d . . .
O3 O 0.29949(6) 0.2538(3) 0.66346(17) 0.0690(6) Uani 1 1 d . . .
O4 O 0.18813(5) 0.12786(19) 0.81686(13) 0.0479(4) Uani 1 1 d . . .
O5 O 0.13886(6) 0.1921(2) 0.44861(15) 0.0650(6) Uani 1 1 d . . .
H5 H 0.1584 0.2044 0.4163 0.097 Uiso 1 1 calc R . .
C1 C 0.37921(8) 0.0335(3) 0.7644(2) 0.0558(6) Uani 1 1 d . . .
H1A H 0.3775 0.0766 0.6889 0.067 Uiso 1 1 calc R . .
H1B H 0.3905 -0.0616 0.7649 0.067 Uiso 1 1 calc R . .
C2 C 0.41298(8) 0.1155(3) 0.8673(2) 0.0523(6) Uani 1 1 d . . .
C3 C 0.39367(8) 0.2607(3) 0.8718(2) 0.0520(6) Uani 1 1 d . . .
H3A H 0.4146 0.3118 0.9393 0.062 Uiso 1 1 calc R . .
H3B H 0.3917 0.3111 0.7991 0.062 Uiso 1 1 calc R . .
C4 C 0.42112(12) 0.0398(4) 0.9861(3) 0.0849(10) Uani 1 1 d . . .
H4A H 0.3921 0.0288 0.9996 0.127 Uiso 1 1 calc R . .
H4B H 0.4420 0.0937 1.0502 0.127 Uiso 1 1 calc R . .
H4C H 0.4344 -0.0509 0.9833 0.127 Uiso 1 1 calc R . .
C5 C 0.45823(10) 0.1306(4) 0.8402(4) 0.0851(10) Uani 1 1 d . . .
H5A H 0.4705 0.0393 0.8341 0.128 Uiso 1 1 calc R . .
H5B H 0.4804 0.1822 0.9037 0.128 Uiso 1 1 calc R . .
H5C H 0.4523 0.1799 0.7658 0.128 Uiso 1 1 calc R . .
C6 C 0.26469(8) 0.1410(2) 0.83217(19) 0.0419(5) Uani 1 1 d . . .
C7 C 0.22046(8) 0.1589(3) 0.7632(2) 0.0451(5) Uani 1 1 d . . .
C8 C 0.20104(9) 0.2196(3) 0.6393(2) 0.0591(7) Uani 1 1 d . . .
H8A H 0.1919 0.3163 0.6444 0.071 Uiso 1 1 calc R . .
H8B H 0.2248 0.2190 0.6019 0.071 Uiso 1 1 calc R . .
C9 C 0.16039(9) 0.1385(4) 0.5646(2) 0.0593(7) Uani 1 1 d . . .
H9 H 0.1706 0.0424 0.5574 0.071 Uiso 1 1 calc R . .
C10 C 0.12510(8) 0.1331(3) 0.6274(2) 0.0475(6) Uani 1 1 d . . .
C11 C 0.07769(9) 0.1314(3) 0.5686(2) 0.0608(7) Uani 1 1 d . . .
H11 H 0.0661 0.1360 0.4853 0.073 Uiso 1 1 calc R . .
C12 C 0.04737(9) 0.1228(4) 0.6321(3) 0.0690(8) Uani 1 1 d . . .
H12 H 0.0155 0.1193 0.5918 0.083 Uiso 1 1 calc R . .
C13 C 0.06461(10) 0.1195(4) 0.7553(3) 0.0750(9) Uani 1 1 d . . .
H13 H 0.0443 0.1147 0.7983 0.090 Uiso 1 1 calc R . .
C14 C 0.11170(9) 0.1233(3) 0.8155(2) 0.0627(7) Uani 1 1 d . . .
H14 H 0.1233 0.1221 0.8990 0.075 Uiso 1 1 calc R . .
C15 C 0.14138(8) 0.1290(2) 0.7505(2) 0.0427(5) Uani 1 1 d . . .
C16 C 0.27780(9) 0.0845(3) 0.9584(2) 0.0569(7) Uani 1 1 d . . .
H16A H 0.2815 0.1611 1.0135 0.085 Uiso 1 1 calc R . .
H16B H 0.3064 0.0335 0.9777 0.085 Uiso 1 1 calc R . .
H16C H 0.2538 0.0231 0.9641 0.085 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'
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 P O2 112.27(12) . . ?
O3 P O1 112.73(12) . . ?
O2 P O1 102.78(9) . . ?
O3 P C6 118.82(11) . . ?
O2 P C6 104.40(10) . . ?
O1 P C6 104.23(10) . . ?
C1 O1 P 115.58(15) . . ?
C3 O2 P 114.15(14) . . ?
C7 O4 C15 120.23(17) . . ?
C9 O5 H5 109.5 . . ?
O1 C1 C2 111.49(19) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 109.3(2) . . ?
C3 C2 C4 110.2(2) . . ?
C1 C2 C4 110.5(3) . . ?
C3 C2 C5 108.2(2) . . ?
C1 C2 C5 107.4(2) . . ?
C4 C2 C5 111.1(2) . . ?
O2 C3 C2 111.6(2) . . ?
O2 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
O2 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
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 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C16 121.8(2) . . ?
C7 C6 P 120.72(17) . . ?
C16 C6 P 117.42(17) . . ?
C6 C7 O4 115.3(2) . . ?
C6 C7 C8 129.3(2) . . ?
O4 C7 C8 115.15(19) . . ?
C9 C8 C7 111.0(2) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O5 C9 C8 114.7(2) . . ?
O5 C9 C10 108.5(2) . . ?
C8 C9 C10 108.7(2) . . ?
O5 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C9 117.5(2) . . ?
C11 C10 C9 123.9(2) . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.6(2) . . ?
C10 C15 O4 122.7(2) . . ?
C14 C15 O4 115.7(2) . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
P O3 1.4624(18) . ?
P O2 1.5783(18) . ?
P O1 1.5797(18) . ?
P C6 1.760(2) . ?
O1 C1 1.453(3) . ?
O2 C3 1.458(3) . ?
O4 C7 1.377(3) . ?
O4 C15 1.381(3) . ?
O5 C9 1.403(3) . ?
O5 H5 0.8200 . ?
C1 C2 1.521(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.512(4) . ?
C2 C4 1.525(4) . ?
C2 C5 1.530(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.335(3) . ?
C6 C16 1.509(3) . ?
C7 C8 1.500(3) . ?
C8 C9 1.478(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.505(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.372(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
O5 H5 O3 0.82 1.88 2.698(2) 175.3 7_556
