#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:15:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178842 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/96/4109681.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_4109681
loop_
_publ_author_name
'Bradley O. Ashburn'
'Rich G. Carter'
'Lev N. Zakharov'
_publ_section_title
;
 Synthesis of Tetra-ortho-substituted, Phosphorus-Containing and
 Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9109
_journal_page_last               9116
_journal_paper_doi               10.1021/ja071163r
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C17 H19 Cl N O7 P'
_chemical_formula_weight         415.75
_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                   15.5818(17)
_cell_length_b                   13.1046(15)
_cell_length_c                   9.3400(10)
_cell_measurement_reflns_used    5306
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.54
_cell_volume                     1907.2(4)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15844
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      0
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1134P)²+1.8053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2173
_reflns_number_gt                1748
_reflns_number_total             2375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071163rsi20070216_084220.cif
_cod_data_source_block           5b
_cod_database_code               4109681
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12953(5) 0.2500 0.46629(10) 0.0421(4) Uani 1 2 d S . .
Cl1 Cl 0.02303(18) 0.0312(2) 0.2036(4) 0.0770(8) Uani 0.50 1 d PD . .
N1 N 0.0240(6) 0.0808(9) 0.1478(8) 0.071(2) Uani 0.50 1 d PD . .
O1 O 0.15069(14) 0.1600(2) 0.5705(2) 0.0590(8) Uani 1 1 d . . .
O2 O 0.17734(16) 0.2500 0.3301(3) 0.0586(10) Uani 1 2 d S . .
O3 O -0.17461(15) 0.2500 0.6809(3) 0.0455(8) Uani 1 2 d S . .
O4 O -0.15171(18) 0.2500 0.1759(3) 0.097(2) Uani 1 2 d S A .
H4A H -0.2054 0.2500 0.1838 0.146 Uiso 1 2 calc SR . .
O5 O -0.0442(5) 0.0649(5) 0.2072(7) 0.089(2) Uani 0.50 1 d PD . .
O6 O 0.0741(5) 0.0075(6) 0.1263(9) 0.095(2) Uani 0.50 1 d PD . .
C1 C -0.1351(2) 0.2500 0.8191(4) 0.0457(11) Uani 1 2 d S . .
C2 C -0.1218(2) 0.2500 0.5645(4) 0.0381(9) Uani 1 2 d S . .
C3 C -0.0329(2) 0.2500 0.5718(4) 0.0358(9) Uani 1 2 d S A .
C4 C 0.01494(19) 0.2500 0.4434(4) 0.0342(9) Uani 1 2 d S . .
C5 C -0.0252(2) 0.2500 0.3111(4) 0.0411(10) Uani 1 2 d S A .
C6 C -0.1157(2) 0.2500 0.3072(4) 0.0553(14) Uani 1 2 d S . .
C7 C -0.1628(2) 0.2500 0.4329(4) 0.0494(13) Uani 1 2 d S A .
C8 C 0.0218(2) 0.2500 0.1712(4) 0.0530(14) Uani 1 2 d S . .
C9 C 0.04578(18) 0.1609(4) 0.1032(4) 0.0692(14) Uani 1 1 d D A .
C10 C 0.0930(2) 0.1610(6) -0.0262(4) 0.098(2) Uani 1 1 d . . .
C11 C 0.1151(3) 0.2500 -0.0894(6) 0.105(4) Uani 1 2 d S . .
C12 C 0.1431(5) 0.0572(6) 0.5118(9) 0.0533(16) Uiso 0.50 1 d P A 1
H12A H 0.0975 0.0573 0.4379 0.064 Uiso 0.50 1 calc PR A 1
H12B H 0.1245 0.0106 0.5893 0.064 Uiso 0.50 1 calc PR A 1
C13 C 0.2234(9) 0.0163(10) 0.4470(13) 0.110(4) Uiso 0.50 1 d P A 1
H13A H 0.2130 -0.0529 0.4110 0.165 Uiso 0.50 1 calc PR A 1
H13B H 0.2687 0.0143 0.5197 0.165 Uiso 0.50 1 calc PR A 1
H13C H 0.2413 0.0604 0.3678 0.165 Uiso 0.50 1 calc PR A 1
C12A C 0.1793(12) 0.0603(12) 0.5476(18) 0.129(5) Uiso 0.50 1 d P A 2
H12C H 0.2192 0.0608 0.4652 0.155 Uiso 0.50 1 calc PR A 2
H12D H 0.1293 0.0178 0.5206 0.155 Uiso 0.50 1 calc PR A 2
C13A C 0.2219(8) 0.0124(9) 0.6671(12) 0.093(3) Uiso 0.50 1 d P A 2
H13D H 0.2409 -0.0561 0.6394 0.140 Uiso 0.50 1 calc PR A 2
H13E H 0.1820 0.0074 0.7479 0.140 Uiso 0.50 1 calc PR A 2
H13F H 0.2718 0.0534 0.6951 0.140 Uiso 0.50 1 calc PR A 2
H1A H -0.104(3) 0.183(3) 0.828(4) 0.054(10) Uiso 1 1 d . . .
H1B H -0.186(3) 0.2500 0.891(5) 0.045(12) Uiso 1 2 d S . .
H3 H -0.002(3) 0.2500 0.673(5) 0.032(10) Uiso 1 2 d S . .
H7 H -0.227(4) 0.2500 0.428(6) 0.061(15) Uiso 1 2 d S . .
H10 H 0.109(4) 0.094(4) -0.059(6) 0.099(17) Uiso 1 1 d . . .
H11 H 0.152(5) 0.2500 -0.180(8) 0.10(2) Uiso 1 2 d S . .
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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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 115.48(10) . 7_565
O2 P1 O1 115.48(10) . .
O1 P1 O1 97.9(2) 7_565 .
O2 P1 C4 113.54(16) . .
O1 P1 C4 106.45(11) 7_565 .
O1 P1 C4 106.45(11) . .
N1 Cl1 O6 78.4(7) . .
N1 Cl1 O5 74.5(8) . .
O6 Cl1 O5 141.5(6) . .
N1 Cl1 C9 13.4(7) . .
O6 Cl1 C9 78.7(4) . .
O5 Cl1 C9 81.1(4) . .
Cl1 N1 C9 157.1(11) . .
Cl1 N1 O5 64.2(8) . .
C9 N1 O5 124.4(9) . .
Cl1 N1 O6 60.9(8) . .
C9 N1 O6 116.5(9) . .
O5 N1 O6 119.0(11) . .
C12A O1 C12 26.5(7) . .
C12A O1 P1 132.6(7) . .
C12 O1 P1 116.4(4) . .
C2 O3 C1 117.4(3) . .
C6 O4 H4A 109.5 . .
Cl1 O5 N1 41.3(5) . .
Cl1 O6 N1 40.7(5) . .
O3 C1 H1A 107(2) . .
O3 C1 H1B 105(3) . .
H1A C1 H1B 108(2) . .
O3 C2 C7 115.4(3) . .
O3 C2 C3 124.3(3) . .
C7 C2 C3 120.3(3) . .
C2 C3 C4 119.1(3) . .
C2 C3 H3 120(2) . .
C4 C3 H3 121(2) . .
C5 C4 C3 121.3(3) . .
C5 C4 P1 123.7(3) . .
C3 C4 P1 115.0(2) . .
C4 C5 C6 118.3(3) . .
C4 C5 C8 123.9(3) . .
C6 C5 C8 117.8(3) . .
O4 C6 C7 123.4(3) . .
O4 C6 C5 116.0(3) . .
C7 C6 C5 120.6(3) . .
C6 C7 C2 120.5(3) . .
C6 C7 H7 120(3) . .
C2 C7 H7 120(3) . .
C9 C8 C9 115.5(5) 7_565 .
C9 C8 C5 122.2(2) 7_565 .
C9 C8 C5 122.2(2) . .
N1 C9 C8 120.8(5) . .
N1 C9 C10 116.9(6) . .
C8 C9 C10 122.2(5) . .
N1 C9 Cl1 9.5(4) . .
C8 C9 Cl1 117.5(3) . .
C10 C9 Cl1 120.0(5) . .
C11 C10 C9 120.4(6) . .
C11 C10 H10 126(3) . .
C9 C10 H10 114(3) . .
C10 C11 C10 119.3(6) 7_565 .
C10 C11 H11 120.3(3) 7_565 .
C10 C11 H11 120.3(3) . .
O1 C12 C13 114.6(7) . .
O1 C12 H12A 108.6 . .
C13 C12 H12A 108.6 . .
O1 C12 H12B 108.6 . .
C13 C12 H12B 108.6 . .
H12A C12 H12B 107.6 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O1 C12A C13A 115.8(12) . .
O1 C12A H12C 108.3 . .
C13A C12A H12C 108.3 . .
O1 C12A H12D 108.3 . .
C13A C12A H12D 108.3 . .
H12C C12A H12D 107.4 . .
C12A C13A H13D 109.5 . .
C12A C13A H13E 109.5 . .
H13D C13A H13E 109.5 . .
C12A C13A H13F 109.5 . .
H13D C13A H13F 109.5 . .
H13E C13A H13F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.474(3) .
P1 O1 1.564(3) 7_565
P1 O1 1.564(3) .
P1 C4 1.798(3) .
Cl1 N1 0.834(9) .
Cl1 O6 1.119(8) .
Cl1 O5 1.138(9) .
Cl1 C9 1.973(6) .
N1 C9 1.178(11) .
N1 O5 1.218(10) .
N1 O6 1.254(10) .
O1 C12A 1.396(16) .
O1 C12 1.459(8) .
O3 C2 1.363(4) .
O3 C1 1.430(5) .
O4 C6 1.349(5) .
O4 H4A 0.8400 .
C1 H1A 1.01(4) .
C1 H1B 1.04(5) .
C2 C7 1.386(5) .
C2 C3 1.387(5) .
C3 C4 1.412(5) .
C3 H3 1.06(4) .
C4 C5 1.385(5) .
C5 C6 1.412(5) .
C5 C8 1.497(5) .
C6 C7 1.384(5) .
C7 H7 1.00(6) .
C8 C9 1.381(5) 7_565
C8 C9 1.381(5) .
C9 C10 1.415(5) .
C10 C11 1.352(8) .
C10 H10 0.96(5) .
C11 C10 1.352(8) 7_565
C11 H11 1.02(8) .
C12 C13 1.491(16) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C12A C13A 1.442(17) .
C12A H12C 0.9900 .
C12A H12D 0.9900 .
C13A H13D 0.9800 .
C13A H13E 0.9800 .
C13A H13F 0.9800 .
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
O4 H4A O2 0.84 1.83 2.664(4) 170.8 6_556
