#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024701.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_4024701
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            'C21 H20 Br O4 P'
_chemical_formula_weight         447.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.655(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0547(18)
_cell_length_b                   8.9540(9)
_cell_length_c                   12.7659(13)
_cell_measurement_reflns_used    7635
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.40
_cell_volume                     1936.3(3)
_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      273(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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18020
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.20
_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    2.230
_exptl_absorpt_correction_T_max  0.6280
_exptl_absorpt_correction_T_min  0.4473
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0348
_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)+(0.0575P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                2820
_reflns_number_total             3406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900896v_si_002_02.cif
_cod_data_source_block           compd(Z)-12
_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      P2(1)/c
_cod_database_code               4024701
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.82231(4) 0.18881(8) -0.05176(5) 0.03239(19) Uani 1 1 d . . .
O1 O 0.89470(11) 0.08249(19) -0.01746(15) 0.0360(5) Uani 1 1 d . . .
O2 O 0.85007(11) 0.3463(2) -0.00646(15) 0.0396(5) Uani 1 1 d . . .
O3 O 0.80404(12) 0.1926(3) -0.16608(15) 0.0512(6) Uani 1 1 d . . .
O4 O 0.66768(10) 0.3234(2) -0.04923(15) 0.0375(5) Uani 1 1 d . . .
Br Br 0.356788(18) 0.57699(4) -0.23966(3) 0.05244(15) Uani 1 1 d . . .
C1 C 0.93690(16) 0.0943(3) 0.0878(2) 0.0366(6) Uani 1 1 d . . .
H1A H 0.9832 0.0306 0.0925 0.044 Uiso 1 1 calc R . .
H1B H 0.9032 0.0586 0.1387 0.044 Uiso 1 1 calc R . .
C2 C 0.96233(17) 0.2525(3) 0.1158(2) 0.0384(7) Uani 1 1 d . . .
C3 C 0.88974(18) 0.3529(3) 0.1005(2) 0.0418(7) Uani 1 1 d . . .
H3A H 0.8531 0.3228 0.1493 0.050 Uiso 1 1 calc R . .
H3B H 0.9055 0.4551 0.1169 0.050 Uiso 1 1 calc R . .
C4 C 1.02522(18) 0.3029(4) 0.0479(3) 0.0489(8) Uani 1 1 d . . .
H4A H 1.0686 0.2339 0.0558 0.073 Uiso 1 1 calc R . .
H4B H 1.0437 0.4006 0.0698 0.073 Uiso 1 1 calc R . .
H4C H 1.0030 0.3061 -0.0247 0.073 Uiso 1 1 calc R . .
C5 C 0.9948(2) 0.2549(5) 0.2326(3) 0.0659(10) Uani 1 1 d . . .
H5A H 0.9544 0.2237 0.2743 0.099 Uiso 1 1 calc R . .
H5B H 1.0115 0.3544 0.2525 0.099 Uiso 1 1 calc R . .
H5C H 1.0390 0.1882 0.2444 0.099 Uiso 1 1 calc R . .
C6 C 0.74378(15) 0.1224(3) 0.0176(2) 0.0317(6) Uani 1 1 d . . .
C7 C 0.67278(16) 0.1905(3) 0.0060(2) 0.0333(6) Uani 1 1 d . . .
C8 C 0.60184(16) 0.1353(3) 0.0437(2) 0.0377(7) Uani 1 1 d . . .
H8 H 0.6052 0.0571 0.0919 0.045 Uiso 1 1 calc R . .
C9 C 0.53152(17) 0.1942(3) 0.0106(2) 0.0378(7) Uani 1 1 d . . .
H9 H 0.4863 0.1553 0.0347 0.045 Uiso 1 1 calc R . .
C10 C 0.52514(16) 0.3180(3) -0.0625(2) 0.0332(6) Uani 1 1 d . . .
C11 C 0.45364(17) 0.3789(3) -0.1082(2) 0.0380(7) Uani 1 1 d . . .
H11 H 0.4060 0.3395 -0.0921 0.046 Uiso 1 1 calc R . .
C12 C 0.45409(17) 0.4968(3) -0.1767(2) 0.0400(7) Uani 1 1 d . . .
C13 C 0.52363(19) 0.5592(3) -0.1999(3) 0.0472(8) Uani 1 1 d . . .
H13 H 0.5227 0.6406 -0.2453 0.057 Uiso 1 1 calc R . .
C14 C 0.59525(17) 0.5008(3) -0.1556(2) 0.0427(7) Uani 1 1 d . . .
H14 H 0.6426 0.5426 -0.1707 0.051 Uiso 1 1 calc R . .
C15 C 0.59508(16) 0.3799(3) -0.0888(2) 0.0331(6) Uani 1 1 d . . .
C16 C 0.75470(15) -0.0201(3) 0.0784(2) 0.0346(6) Uani 1 1 d . . .
C17 C 0.75600(19) -0.1553(3) 0.0258(3) 0.0501(8) Uani 1 1 d . . .
H17 H 0.7478 -0.1578 -0.0475 0.060 Uiso 1 1 calc R . .
C18 C 0.7696(2) -0.2873(4) 0.0824(4) 0.0656(11) Uani 1 1 d . . .
H18 H 0.7700 -0.3778 0.0468 0.079 Uiso 1 1 calc R . .
C19 C 0.7823(2) -0.2851(4) 0.1905(4) 0.0657(11) Uani 1 1 d . . .
H19 H 0.7922 -0.3736 0.2278 0.079 Uiso 1 1 calc R . .
C20 C 0.7804(2) -0.1525(4) 0.2433(3) 0.0576(9) Uani 1 1 d . . .
H20 H 0.7885 -0.1514 0.3166 0.069 Uiso 1 1 calc R . .
C21 C 0.76637(17) -0.0198(4) 0.1884(2) 0.0433(7) Uani 1 1 d . . .
H21 H 0.7648 0.0697 0.2250 0.052 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'
Br Br -0.2901 2.4595 '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 111.52(12) . . ?
O3 P O1 111.17(12) . . ?
O2 P O1 104.22(10) . . ?
O3 P C6 114.68(12) . . ?
O2 P C6 109.02(12) . . ?
O1 P C6 105.55(11) . . ?
C1 O1 P 119.98(16) . . ?
C3 O2 P 117.91(17) . . ?
C15 O4 C7 120.3(2) . . ?
O1 C1 C2 112.6(2) . . ?
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 110.2(2) . . ?
C1 C2 C3 108.4(2) . . ?
C4 C2 C3 111.6(2) . . ?
C1 C2 C5 107.8(3) . . ?
C4 C2 C5 110.5(3) . . ?
C3 C2 C5 108.3(3) . . ?
O2 C3 C2 112.3(2) . . ?
O2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
O2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
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 120.0(2) . . ?
C7 C6 P 120.6(2) . . ?
C16 C6 P 119.03(19) . . ?
C6 C7 O4 116.6(2) . . ?
C6 C7 C8 125.9(3) . . ?
O4 C7 C8 117.4(2) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C15 C10 C11 118.3(3) . . ?
C15 C10 C9 117.3(2) . . ?
C11 C10 C9 124.4(3) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 Br 119.5(2) . . ?
C13 C12 Br 119.2(2) . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 O4 116.7(2) . . ?
C14 C15 C10 121.7(3) . . ?
O4 C15 C10 121.6(2) . . ?
C17 C16 C21 118.8(3) . . ?
C17 C16 C6 120.2(3) . . ?
C21 C16 C6 121.0(3) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
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 1.457(2) . ?
P O2 1.576(2) . ?
P O1 1.5802(19) . ?
P C6 1.790(3) . ?
O1 C1 1.453(3) . ?
O2 C3 1.453(3) . ?
O4 C15 1.378(3) . ?
O4 C7 1.381(3) . ?
Br C12 1.899(3) . ?
C1 C2 1.511(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.524(4) . ?
C2 C3 1.524(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 1.349(4) . ?
C6 C16 1.494(4) . ?
C7 C8 1.440(4) . ?
C8 C9 1.333(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.445(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.391(4) . ?
C10 C11 1.400(4) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.385(4) . ?
C16 C21 1.396(4) . ?
C17 C18 1.391(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659002
