#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/45/7104507.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_7104507
loop_
_publ_author_name
'Shi, Baolu'
'Blake, Alexander J'
'Campbell, Ian B'
'Judkins, Brian D'
'Moody, Christopher J'
_publ_section_title
;
 The rhodium carbene route to oxazoles: a remarkable catalyst effect.
;
_journal_issue                   22
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3291
_journal_page_last               3293
_journal_paper_doi               10.1039/b903878g
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C12 H16 N O5 P'
_chemical_formula_sum            'C12 H16 N O5 P'
_chemical_formula_weight         285.23
_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
'N-H from delta-F; Me from delta-F; others placed geometrically'
_atom_sites_solution_primary     direct
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 114.006(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.2037(9)
_cell_length_b                   8.6712(4)
_cell_length_c                   20.5323(11)
_cell_measurement_reflns_used    3850
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.9
_cell_measurement_theta_min      2.2
_cell_volume                     2798.0(4)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12210
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Bruker SHELXTL; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'kite-shaped plate'
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment
'N-H freely refined; rigid rotor for all Me; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0345
_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)+(0.061P)²+1.672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2994
_reflns_number_total             3210
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b903878g.txt
_cod_data_source_block           ampome
_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      'C 2/c'
_cod_database_code               7104507
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
C1 C 0.18294(10) 0.63218(16) 0.54872(7) 0.0338(3) Uani 1 1 d . . .
H1A H 0.2122 0.7254 0.5436 0.051 Uiso 1 1 calc R . .
H1B H 0.2210 0.5730 0.5901 0.051 Uiso 1 1 calc R . .
H1C H 0.1318 0.6614 0.5556 0.051 Uiso 1 1 calc R . .
C2 C 0.15828(8) 0.53565(14) 0.48288(7) 0.0248(2) Uani 1 1 d . . .
O3 O 0.17398(7) 0.57137(12) 0.43270(6) 0.0391(3) Uani 1 1 d . . .
C4 C 0.10861(7) 0.38786(13) 0.48074(6) 0.0198(2) Uani 1 1 d . . .
H4 H 0.0494 0.4195 0.4723 0.024 Uiso 1 1 calc R . .
P5 P 0.100438(18) 0.25758(4) 0.408693(15) 0.02185(11) Uani 1 1 d . . .
O6 O 0.18278(6) 0.21388(12) 0.40841(5) 0.0300(2) Uani 1 1 d . . .
O7 O 0.03937(6) 0.33187(12) 0.33687(5) 0.0313(2) Uani 1 1 d . . .
C8 C -0.04987(8) 0.35982(18) 0.31910(7) 0.0359(3) Uani 1 1 d . . .
H8A H -0.0759 0.2664 0.3283 0.054 Uiso 1 1 calc R . .
H8B H -0.0785 0.3875 0.2686 0.054 Uiso 1 1 calc R . .
H8C H -0.0557 0.4445 0.3484 0.054 Uiso 1 1 calc R . .
O9 O 0.04779(6) 0.11776(11) 0.41863(5) 0.0310(2) Uani 1 1 d . . .
C10 C 0.08930(10) -0.01971(17) 0.45656(9) 0.0403(3) Uani 1 1 d . . .
H10A H 0.1511 -0.0073 0.4743 0.060 Uiso 1 1 calc R . .
H10B H 0.0713 -0.1085 0.4243 0.060 Uiso 1 1 calc R . .
H10C H 0.0736 -0.0366 0.4968 0.060 Uiso 1 1 calc R . .
N11 N 0.14269(6) 0.30316(12) 0.54755(5) 0.0208(2) Uani 1 1 d . . .
H11N H 0.1939(12) 0.279(2) 0.5634(9) 0.034(4) Uiso 1 1 d . . .
C12 C 0.09447(7) 0.27767(13) 0.58458(6) 0.0202(2) Uani 1 1 d . . .
O13 O 0.02332(5) 0.33399(10) 0.56687(5) 0.0268(2) Uani 1 1 d . . .
C14 C 0.13163(7) 0.17324(14) 0.64829(6) 0.0227(2) Uani 1 1 d . . .
C15 C 0.09259(9) 0.17183(16) 0.69611(7) 0.0304(3) Uani 1 1 d . . .
H15 H 0.0463 0.2392 0.6890 0.036 Uiso 1 1 calc R . .
C16 C 0.12150(10) 0.07187(19) 0.75397(7) 0.0384(3) Uani 1 1 d . . .
H16 H 0.0953 0.0720 0.7868 0.046 Uiso 1 1 calc R . .
C17 C 0.18808(10) -0.02762(18) 0.76406(7) 0.0383(3) Uani 1 1 d . . .
H17 H 0.2071 -0.0968 0.8033 0.046 Uiso 1 1 calc R . .
C18 C 0.22722(9) -0.02667(17) 0.71700(7) 0.0362(3) Uani 1 1 d . . .
H18 H 0.2732 -0.0948 0.7242 0.043 Uiso 1 1 calc R . .
C19 C 0.19937(8) 0.07388(15) 0.65905(7) 0.0285(3) Uani 1 1 d . . .
H19 H 0.2265 0.0746 0.6270 0.034 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'
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'
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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 C1 123.20(11) . . ?
O3 C2 C4 120.42(11) . . ?
C1 C2 C4 116.35(10) . . ?
N11 C4 C2 112.95(9) . . ?
N11 C4 P5 108.76(8) . . ?
C2 C4 P5 113.61(8) . . ?
N11 C4 H4 107.0 . . ?
C2 C4 H4 107.0 . . ?
P5 C4 H4 107.0 . . ?
O6 P5 O7 112.50(5) . . ?
O6 P5 O9 114.09(6) . . ?
O7 P5 O9 103.80(5) . . ?
O6 P5 C4 114.05(5) . . ?
O7 P5 C4 108.15(5) . . ?
O9 P5 C4 103.34(5) . . ?
C8 O7 P5 123.03(8) . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 O9 P5 121.39(8) . . ?
O9 C10 H10A 109.5 . . ?
O9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 N11 C4 120.62(10) . . ?
C12 N11 H11N 122.3(12) . . ?
C4 N11 H11N 116.8(12) . . ?
O13 C12 N11 122.30(10) . . ?
O13 C12 C14 121.14(10) . . ?
N11 C12 C14 116.54(10) . . ?
C19 C14 C15 119.58(11) . . ?
C19 C14 C12 122.87(11) . . ?
C15 C14 C12 117.46(11) . . ?
C16 C15 C14 119.96(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.31(13) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.06(12) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.26(13) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.82(12) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
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
C1 C2 1.4970(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O3 1.2070(16) . ?
C2 C4 1.5310(16) . ?
C4 N11 1.4528(14) . ?
C4 P5 1.8207(11) . ?
C4 H4 1.0000 . ?
P5 O6 1.4687(9) . ?
P5 O7 1.5598(9) . ?
P5 O9 1.5755(9) . ?
O7 C8 1.4467(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O9 C10 1.4439(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N11 C12 1.3520(15) . ?
N11 H11N 0.831(18) . ?
C12 O13 1.2276(14) . ?
C12 C14 1.5032(15) . ?
C14 C19 1.3928(17) . ?
C14 C15 1.3969(17) . ?
C15 C16 1.3891(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3934(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
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
N11 H11N O6 0.83(2) 1.96(2) 2.7651(14) 163(2) 7_556
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C2 C4 N11 138.40(12) . . . . ?
C1 C2 C4 N11 -43.33(14) . . . . ?
O3 C2 C4 P5 13.92(15) . . . . ?
C1 C2 C4 P5 -167.81(9) . . . . ?
N11 C4 P5 O6 -71.31(9) . . . . ?
C2 C4 P5 O6 55.40(10) . . . . ?
N11 C4 P5 O7 162.73(7) . . . . ?
C2 C4 P5 O7 -70.56(9) . . . . ?
N11 C4 P5 O9 53.11(8) . . . . ?
C2 C4 P5 O9 179.82(8) . . . . ?
O6 P5 O7 C8 168.85(10) . . . . ?
O9 P5 O7 C8 45.02(12) . . . . ?
C4 P5 O7 C8 -64.29(12) . . . . ?
O6 P5 O9 C10 27.75(12) . . . . ?
O7 P5 O9 C10 150.54(10) . . . . ?
C4 P5 O9 C10 -96.64(11) . . . . ?
C2 C4 N11 C12 119.07(11) . . . . ?
P5 C4 N11 C12 -113.85(10) . . . . ?
C4 N11 C12 O13 -5.74(17) . . . . ?
C4 N11 C12 C14 172.98(10) . . . . ?
O13 C12 C14 C19 161.46(12) . . . . ?
N11 C12 C14 C19 -17.27(17) . . . . ?
O13 C12 C14 C15 -15.07(17) . . . . ?
N11 C12 C14 C15 166.20(11) . . . . ?
C19 C14 C15 C16 0.09(19) . . . . ?
C12 C14 C15 C16 176.74(12) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C15 C14 C19 C18 0.44(19) . . . . ?
C12 C14 C19 C18 -176.02(12) . . . . ?
C17 C18 C19 C14 -0.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24807658
