#------------------------------------------------------------------------------
#$Date: 2017-02-04 03:25:06 +0100 (Sat 04 de Feb de 2017) $
#$Revision: 191381 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/49/1544934.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_1544934
loop_
_publ_author_name
'Phatake, Ravindra S.'
'Mullapudi, Venkannababu'
'Wakchaure, Vivek C.'
'Ramana, Chepuri V.'
_publ_section_title
;
 Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              372
_journal_page_last               375
_journal_paper_doi               10.1021/acs.orglett.6b03573
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24
_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                 99.138(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.798(2)
_cell_length_b                   17.333(4)
_cell_length_c                   7.162(2)
_cell_measurement_reflns_used    2712
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.34
_cell_volume                     1078.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7736
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   MULTI-SCAN'
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.1026
_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)+(0.0396P)²+5.4840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2150
_refine_ls_wR_factor_ref         0.2232
_reflns_number_gt                1562
_reflns_number_total             1912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03573_si_003.cif
_cod_data_source_block           rv_01
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544934--1544935.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1544934
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
O1 O -0.0085(4) -0.18146(19) 0.3031(6) 0.0342(9) Uani 1 1 d .
N1 N 0.4307(5) 0.2903(2) 0.3543(6) 0.0292(10) Uani 1 1 d .
N2 N 0.1145(4) 0.0654(2) 0.2261(5) 0.0226(9) Uani 1 1 d .
N3 N 0.1797(4) -0.0042(2) 0.2615(5) 0.0225(9) Uani 1 1 d .
C1 C 0.3649(5) 0.2360(3) 0.3733(7) 0.0236(11) Uani 1 1 d .
C2 C 0.2777(6) 0.1649(3) 0.3955(7) 0.0268(11) Uani 1 1 d .
H2A H 0.1943 0.1761 0.4695 0.032 Uiso 1 1 calc R
H2B H 0.3469 0.1260 0.4657 0.032 Uiso 1 1 calc R
C3 C 0.2088(6) 0.1327(3) 0.2034(7) 0.0278(12) Uani 1 1 d .
H3A H 0.1450 0.1727 0.1299 0.033 Uiso 1 1 calc R
H3B H 0.2924 0.1181 0.1327 0.033 Uiso 1 1 calc R
C4 C -0.0434(5) 0.0629(3) 0.2135(6) 0.0198(10) Uani 1 1 d .
C5 C -0.1529(6) 0.1215(3) 0.1814(7) 0.0292(12) Uani 1 1 d .
H5 H -0.1248 0.1737 0.1657 0.035 Uiso 1 1 calc R
C6 C -0.3044(6) 0.0993(3) 0.1738(8) 0.0344(13) Uani 1 1 d .
H6 H -0.3829 0.1373 0.1527 0.041 Uiso 1 1 calc R
C7 C -0.3455(6) 0.0218(3) 0.1964(7) 0.0297(12) Uani 1 1 d .
H7 H -0.4513 0.0090 0.1894 0.036 Uiso 1 1 calc R
C8 C -0.2378(5) -0.0357(3) 0.2282(6) 0.0202(10) Uani 1 1 d .
H8 H -0.2673 -0.0879 0.2424 0.024 Uiso 1 1 calc R
C9 C -0.0808(5) -0.0149(2) 0.2394(6) 0.0181(10) Uani 1 1 d .
C10 C 0.0646(5) -0.0532(3) 0.2695(6) 0.0175(10) Uani 1 1 d .
C11 C 0.0968(5) -0.1359(3) 0.3022(7) 0.0232(11) Uani 1 1 d .
C12 C 0.2610(6) -0.1609(3) 0.3347(8) 0.0348(13) Uani 1 1 d .
H12A H 0.2719 -0.2075 0.4133 0.052 Uiso 1 1 calc R
H12B H 0.3252 -0.1197 0.3993 0.052 Uiso 1 1 calc R
H12C H 0.2938 -0.1720 0.2130 0.052 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.034(2) 0.0177(18) 0.053(2) 0.0003(16) 0.0114(18) -0.0037(16)
N1 0.025(2) 0.027(2) 0.036(3) -0.0023(19) 0.0048(18) -0.0033(19)
N2 0.029(2) 0.019(2) 0.019(2) 0.0000(16) 0.0016(16) -0.0068(17)
N3 0.026(2) 0.021(2) 0.021(2) -0.0031(17) 0.0036(16) -0.0035(17)
C1 0.023(2) 0.027(3) 0.021(2) -0.006(2) 0.0041(19) -0.003(2)
C2 0.036(3) 0.025(3) 0.019(2) -0.003(2) 0.005(2) -0.007(2)
C3 0.038(3) 0.026(3) 0.019(3) 0.000(2) 0.006(2) -0.006(2)
C4 0.028(3) 0.015(2) 0.017(2) 0.0010(18) 0.0030(19) -0.0037(19)
C5 0.037(3) 0.021(3) 0.028(3) 0.000(2) 0.000(2) 0.005(2)
C6 0.032(3) 0.032(3) 0.036(3) 0.004(2) -0.005(2) 0.012(2)
C7 0.024(3) 0.039(3) 0.026(3) 0.002(2) 0.005(2) 0.003(2)
C8 0.024(2) 0.024(3) 0.012(2) -0.0048(19) 0.0020(18) -0.002(2)
C9 0.027(2) 0.017(2) 0.010(2) -0.0017(17) 0.0029(18) -0.0026(19)
C10 0.022(2) 0.020(2) 0.012(2) -0.0011(18) 0.0051(17) -0.0009(19)
C11 0.027(3) 0.021(3) 0.023(3) 0.001(2) 0.008(2) -0.001(2)
C12 0.033(3) 0.030(3) 0.043(3) 0.007(2) 0.008(2) 0.006(2)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 N2 C4 112.3(4)
N3 N2 C3 120.5(4)
C4 N2 C3 127.2(4)
C10 N3 N2 106.1(4)
N1 C1 C2 179.2(5)
C1 C2 C3 110.4(4)
C1 C2 H2A 109.6
C3 C2 H2A 109.6
C1 C2 H2B 109.6
C3 C2 H2B 109.6
H2A C2 H2B 108.1
N2 C3 C2 110.2(4)
N2 C3 H3A 109.6
C2 C3 H3A 109.6
N2 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.1
N2 C4 C5 130.6(4)
N2 C4 C9 106.0(4)
C5 C4 C9 123.4(4)
C6 C5 C4 116.2(5)
C6 C5 H5 121.9
C4 C5 H5 121.9
C5 C6 C7 121.7(5)
C5 C6 H6 119.1
C7 C6 H6 119.1
C8 C7 C6 122.0(5)
C8 C7 H7 119.0
C6 C7 H7 119.0
C7 C8 C9 117.8(4)
C7 C8 H8 121.1
C9 C8 H8 121.1
C4 C9 C8 118.9(4)
C4 C9 C10 104.1(4)
C8 C9 C10 137.1(4)
N3 C10 C9 111.5(4)
N3 C10 C11 120.0(4)
C9 C10 C11 128.5(4)
O1 C11 C10 120.3(4)
O1 C11 C12 122.0(4)
C10 C11 C12 117.7(4)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.218(6)
N1 C1 1.125(6)
N2 N3 1.342(5)
N2 C4 1.379(6)
N2 C3 1.456(6)
N3 C10 1.329(6)
C1 C2 1.474(7)
C2 C3 1.518(7)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.393(7)
C4 C9 1.407(6)
C5 C6 1.380(7)
C5 H5 0.9500
C6 C7 1.407(8)
C6 H6 0.9500
C7 C8 1.370(7)
C7 H7 0.9500
C8 C9 1.417(6)
C8 H8 0.9500
C9 C10 1.427(6)
C10 C11 1.472(6)
C11 C12 1.490(7)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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
C4 N2 N3 C10 0.9(5)
C3 N2 N3 C10 -178.4(4)
N1 C1 C2 C3 17(39)
N3 N2 C3 C2 -82.0(5)
C4 N2 C3 C2 98.9(5)
C1 C2 C3 N2 -176.3(4)
N3 N2 C4 C5 179.1(5)
C3 N2 C4 C5 -1.7(8)
N3 N2 C4 C9 -1.2(5)
C3 N2 C4 C9 178.1(4)
N2 C4 C5 C6 179.0(5)
C9 C4 C5 C6 -0.7(7)
C4 C5 C6 C7 -0.2(8)
C5 C6 C7 C8 0.4(8)
C6 C7 C8 C9 0.5(7)
N2 C4 C9 C8 -178.2(4)
C5 C4 C9 C8 1.6(7)
N2 C4 C9 C10 0.9(5)
C5 C4 C9 C10 -179.3(4)
C7 C8 C9 C4 -1.4(6)
C7 C8 C9 C10 179.9(5)
N2 N3 C10 C9 -0.3(5)
N2 N3 C10 C11 178.6(4)
C4 C9 C10 N3 -0.4(5)
C8 C9 C10 N3 178.4(5)
C4 C9 C10 C11 -179.1(4)
C8 C9 C10 C11 -0.2(8)
N3 C10 C11 O1 -177.4(4)
C9 C10 C11 O1 1.2(7)
N3 C10 C11 C12 2.9(6)
C9 C10 C11 C12 -178.5(4)
