#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024704.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_4024704
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 H20 Br O5 P'
_chemical_formula_weight         403.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_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            8
_cell_length_a                   21.347(2)
_cell_length_b                   21.347(2)
_cell_length_c                   7.5132(16)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.70
_cell_volume                     3423.6(9)
_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      296(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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16208
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.35
_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    2.516
_exptl_absorpt_correction_T_max  0.6601
_exptl_absorpt_correction_T_min  0.4998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0458
_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)+(0.0536P)²+7.1251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                2710
_reflns_number_total             3000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900896v_si_002_05.cif
_cod_data_source_block           compdtrans-24
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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      I-4
_cod_database_code               4024704
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+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 0.84287(5) 0.85142(5) 0.16137(15) 0.0422(3) Uani 1 1 d . . .
O1 O 0.80408(16) 0.90984(15) 0.2252(5) 0.0553(9) Uani 1 1 d . . .
O2 O 0.81349(14) 0.79332(14) 0.2563(4) 0.0462(7) Uani 1 1 d . . .
O3 O 0.84183(18) 0.84692(19) -0.0315(4) 0.0635(9) Uani 1 1 d . . .
O4 O 0.93158(16) 0.77807(17) 0.4711(4) 0.0550(9) Uani 1 1 d . . .
O5 O 1.03098(17) 0.84583(19) 0.1989(6) 0.0558(10) Uani 1 1 d . . .
Br Br 0.99821(4) 0.59089(3) -0.09356(13) 0.1043(4) Uani 1 1 d . . .
C1 C 0.7697(2) 0.9113(2) 0.3919(7) 0.0547(12) Uani 1 1 d . . .
H1A H 0.7410 0.9465 0.3906 0.066 Uiso 1 1 calc R . .
H1B H 0.7989 0.9176 0.4891 0.066 Uiso 1 1 calc R . .
C2 C 0.7334(2) 0.8522(2) 0.4243(7) 0.0523(11) Uani 1 1 d . . .
C3 C 0.7787(2) 0.7975(2) 0.4252(7) 0.0490(10) Uani 1 1 d . . .
H3A H 0.8081 0.8026 0.5226 0.059 Uiso 1 1 calc R . .
H3B H 0.7557 0.7589 0.4444 0.059 Uiso 1 1 calc R . .
C4 C 0.6822(2) 0.8415(3) 0.2883(9) 0.0733(17) Uani 1 1 d . . .
H4A H 0.6998 0.8425 0.1708 0.110 Uiso 1 1 calc R . .
H4B H 0.6511 0.8738 0.2992 0.110 Uiso 1 1 calc R . .
H4C H 0.6631 0.8014 0.3086 0.110 Uiso 1 1 calc R . .
C5 C 0.7059(3) 0.8582(3) 0.6140(9) 0.0762(18) Uani 1 1 d . . .
H5A H 0.6838 0.8972 0.6245 0.114 Uiso 1 1 calc R . .
H5B H 0.7392 0.8569 0.6996 0.114 Uiso 1 1 calc R . .
H5C H 0.6775 0.8241 0.6357 0.114 Uiso 1 1 calc R . .
C6 C 0.92342(19) 0.8634(2) 0.2457(6) 0.0391(9) Uani 1 1 d . . .
C7 C 0.97075(19) 0.8259(2) 0.1362(6) 0.0416(9) Uani 1 1 d . . .
H7 H 0.9661 0.8352 0.0091 0.050 Uiso 1 1 calc R . .
C8 C 0.96370(19) 0.7570(2) 0.1691(6) 0.0420(9) Uani 1 1 d . . .
C9 C 0.9782(2) 0.7123(2) 0.0420(7) 0.0514(11) Uani 1 1 d . . .
H9 H 0.9894 0.7250 -0.0722 0.062 Uiso 1 1 calc R . .
C10 C 0.9764(2) 0.6505(2) 0.0814(9) 0.0614(14) Uani 1 1 d . . .
C11 C 0.9597(3) 0.6306(2) 0.2520(10) 0.0690(17) Uani 1 1 d . . .
H11 H 0.9594 0.5882 0.2797 0.083 Uiso 1 1 calc R . .
C12 C 0.9436(2) 0.6741(2) 0.3786(8) 0.0612(14) Uani 1 1 d . . .
H12 H 0.9310 0.6614 0.4915 0.073 Uiso 1 1 calc R . .
C13 C 0.9463(2) 0.7375(2) 0.3354(7) 0.0471(10) Uani 1 1 d . . .
C14 C 0.92768(19) 0.8430(2) 0.4394(6) 0.0438(10) Uani 1 1 d . . .
C15 C 0.9252(2) 0.8786(3) 0.5777(8) 0.0642(14) Uani 1 1 d . . .
H15A H 0.9261 0.8611 0.6910 0.077 Uiso 1 1 calc R . .
H15B H 0.9226 0.9218 0.5642 0.077 Uiso 1 1 calc R . .
C16 C 0.9376(2) 0.9339(2) 0.2215(8) 0.0582(13) Uani 1 1 d . . .
H16A H 0.9786 0.9430 0.2671 0.087 Uiso 1 1 calc R . .
H16B H 0.9070 0.9581 0.2851 0.087 Uiso 1 1 calc R . .
H16C H 0.9359 0.9443 0.0974 0.087 Uiso 1 1 calc R . .
H5 H 1.051(3) 0.836(3) 0.141(10) 0.08(3) Uiso 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'
O O 0.0106 0.0060 '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'
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 113.4(2) . . ?
O3 P O1 110.4(2) . . ?
O2 P O1 106.21(18) . . ?
O3 P C6 111.4(2) . . ?
O2 P C6 109.09(19) . . ?
O1 P C6 106.0(2) . . ?
C1 O1 P 123.1(3) . . ?
C3 O2 P 123.2(3) . . ?
C13 O4 C14 120.6(4) . . ?
C7 O5 H5 105(7) . . ?
O1 C1 C2 112.5(4) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C4 113.0(5) . . ?
C1 C2 C3 108.6(4) . . ?
C4 C2 C3 110.4(5) . . ?
C1 C2 C5 106.0(5) . . ?
C4 C2 C5 111.1(5) . . ?
C3 C2 C5 107.6(4) . . ?
O2 C3 C2 111.4(4) . . ?
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 . . ?
C14 C6 C7 108.9(3) . . ?
C14 C6 C16 112.3(4) . . ?
C7 C6 C16 108.6(4) . . ?
C14 C6 P 110.1(3) . . ?
C7 C6 P 110.9(3) . . ?
C16 C6 P 106.1(3) . . ?
O5 C7 C8 109.1(4) . . ?
O5 C7 C6 105.0(4) . . ?
C8 C7 C6 111.0(3) . . ?
O5 C7 H7 110.5 . . ?
C8 C7 H7 110.5 . . ?
C6 C7 H7 110.5 . . ?
C13 C8 C9 118.7(4) . . ?
C13 C8 C7 118.5(4) . . ?
C9 C8 C7 122.6(4) . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.3(5) . . ?
C9 C10 Br 119.8(5) . . ?
C11 C10 Br 119.8(4) . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.0(5) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C8 C13 O4 123.2(4) . . ?
C8 C13 C12 121.3(5) . . ?
O4 C13 C12 115.5(5) . . ?
C15 C14 O4 116.5(5) . . ?
C15 C14 C6 126.8(5) . . ?
O4 C14 C6 116.5(4) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
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 1.452(4) . ?
P O2 1.562(3) . ?
P O1 1.572(4) . ?
P C6 1.850(4) . ?
O1 C1 1.452(6) . ?
O2 C3 1.473(6) . ?
O4 C13 1.374(6) . ?
O4 C14 1.409(6) . ?
O5 C7 1.434(6) . ?
O5 H5 0.64(7) . ?
Br C10 1.888(5) . ?
C1 C2 1.501(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.514(8) . ?
C2 C3 1.515(6) . ?
C2 C5 1.547(8) . ?
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 C14 1.522(6) . ?
C6 C7 1.530(6) . ?
C6 C16 1.544(6) . ?
C7 C8 1.498(6) . ?
C7 H7 0.9800 . ?
C8 C13 1.368(7) . ?
C8 C9 1.386(6) . ?
C9 C10 1.353(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(9) . ?
C11 C12 1.372(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(7) . ?
C12 H12 0.9300 . ?
C14 C15 1.288(7) . ?
C15 H15A 0.9300 . ?
C15 H15B 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 0.64(7) 2.34(7) 2.895(6) 146(8) 4_755
