#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/51/4025116.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_4025116
loop_
_publ_author_name
'Matthew R. Smith'
'Alexander J. Blake'
'Christopher J. Hayes'
'Malcolm F. G. Stevens'
'Christopher J. Moody'
_publ_section_title
;
Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and
Aromatic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9372
_journal_page_last               9380
_journal_paper_doi               10.1021/jo902165w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C17 H15 N3 O2, H2 O'
_chemical_formula_sum            'C17 H17 N3 O3'
_chemical_formula_weight         311.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens
'water H atoms 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                 104.200(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.273(2)
_cell_length_b                   22.469(5)
_cell_length_c                   9.528(2)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      2.4
_cell_volume                     1509.4(10)
_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         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.137
_diffrn_reflns_av_sigmaI/netI    0.081
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13082
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             656
_exptl_crystal_size_max          1.08
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.30
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    'rigid rotor; riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3474
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0526
_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)+(0.052P)²+0.242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.130
_refine_ls_wR_factor_ref         0.136
_reflns_number_gt                2965
_reflns_number_total             3474
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo902165w_si_001.cif
_cod_data_source_block           pyimet
_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      'P 21/n'
_cod_database_code               4025116
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.76280(17) -0.06986(6) -0.12588(12) 0.0220(3) Uani 1 1 d . . .
C2 C 0.78372(19) -0.08285(7) 0.01718(14) 0.0204(3) Uani 1 1 d . . .
N3 N 0.77233(16) -0.03575(6) 0.10194(12) 0.0212(3) Uani 1 1 d . . .
C4 C 0.74190(19) 0.01145(6) 0.00814(14) 0.0199(3) Uani 1 1 d . . .
C5 C 0.73633(19) -0.01098(6) -0.12824(14) 0.0196(3) Uani 1 1 d . . .
C6 C 0.80964(19) -0.14372(6) 0.07461(15) 0.0220(3) Uani 1 1 d . . .
C7 C 0.8401(2) -0.15364(7) 0.22390(16) 0.0249(3) Uani 1 1 d . . .
H7 H 0.8485 -0.1207 0.2876 0.030 Uiso 1 1 calc R . .
C8 C 0.8581(2) -0.21073(7) 0.27937(17) 0.0290(3) Uani 1 1 d . . .
H8 H 0.8783 -0.2167 0.3807 0.035 Uiso 1 1 calc R . .
C9 C 0.8470(2) -0.25934(7) 0.18800(18) 0.0316(4) Uani 1 1 d . . .
H9 H 0.8590 -0.2986 0.2263 0.038 Uiso 1 1 calc R . .
C10 C 0.8181(2) -0.25012(7) 0.04019(17) 0.0309(4) Uani 1 1 d . . .
H10 H 0.8109 -0.2833 -0.0228 0.037 Uiso 1 1 calc R . .
C11 C 0.7998(2) -0.19296(7) -0.01644(16) 0.0265(3) Uani 1 1 d . . .
H11 H 0.7804 -0.1873 -0.1178 0.032 Uiso 1 1 calc R . .
O12 O 0.73819(16) 0.08722(5) 0.18103(11) 0.0297(3) Uani 1 1 d . . .
C12 C 0.73003(19) 0.07246(7) 0.05717(15) 0.0211(3) Uani 1 1 d . . .
O13 O 0.71076(15) 0.11122(5) -0.05257(10) 0.0244(3) Uani 1 1 d . . .
C13 C 0.6969(2) 0.17372(7) -0.01834(16) 0.0258(3) Uani 1 1 d . . .
H13A H 0.8121 0.1866 0.0542 0.031 Uiso 1 1 calc R . .
H13B H 0.5853 0.1807 0.0217 0.031 Uiso 1 1 calc R . .
C14 C 0.6770(2) 0.20772(7) -0.15708(18) 0.0315(4) Uani 1 1 d . . .
H14A H 0.6673 0.2504 -0.1385 0.047 Uiso 1 1 calc R . .
H14B H 0.5625 0.1945 -0.2278 0.047 Uiso 1 1 calc R . .
H14C H 0.7883 0.2004 -0.1955 0.047 Uiso 1 1 calc R . .
N N 0.69847(16) 0.02097(5) -0.26379(12) 0.0194(3) Uani 1 1 d . . .
C15 C 0.8342(2) 0.02432(7) -0.33842(15) 0.0241(3) Uani 1 1 d . . .
H15 H 0.9543 0.0062 -0.3013 0.029 Uiso 1 1 calc R . .
C16 C 0.7974(2) 0.05414(7) -0.46838(16) 0.0283(3) Uani 1 1 d . . .
H16 H 0.8913 0.0562 -0.5221 0.034 Uiso 1 1 calc R . .
C17 C 0.6230(2) 0.08110(7) -0.52054(16) 0.0273(3) Uani 1 1 d . . .
H17A H 0.5959 0.1014 -0.6108 0.033 Uiso 1 1 calc R . .
C18 C 0.4881(2) 0.07828(7) -0.44010(15) 0.0256(3) Uani 1 1 d . . .
H18 H 0.3691 0.0976 -0.4735 0.031 Uiso 1 1 calc R . .
C19 C 0.5279(2) 0.04732(7) -0.31147(15) 0.0223(3) Uani 1 1 d . . .
H19 H 0.4355 0.0445 -0.2565 0.027 Uiso 1 1 calc R . .
O1W O 1.10657(18) 0.12920(6) 0.35199(13) 0.0350(3) Uani 1 1 d D . .
H1W1 H 0.9901(13) 0.1292(9) 0.3157(19) 0.034(5) Uiso 1 1 d D . .
H1W2 H 1.154(3) 0.1153(11) 0.2879(19) 0.061(7) Uiso 1 1 d 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 102.05(12) . . ?
N3 C2 N1 115.00(13) . . ?
N3 C2 C6 122.01(12) . . ?
N1 C2 C6 122.96(13) . . ?
C2 N3 C4 103.96(11) . . ?
N3 C4 C5 107.05(13) . . ?
N3 C4 C12 122.13(12) . . ?
C5 C4 C12 130.74(13) . . ?
N1 C5 C4 111.94(12) . . ?
N1 C5 N 120.16(12) . . ?
C4 C5 N 127.84(13) . . ?
C11 C6 C7 118.38(14) . . ?
C11 C6 C2 121.60(13) . . ?
C7 C6 C2 120.00(13) . . ?
C8 C7 C6 120.81(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.39(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.38(15) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.62(15) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C6 120.43(14) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
O12 C12 O13 123.48(14) . . ?
O12 C12 C4 125.19(13) . . ?
O13 C12 C4 111.33(11) . . ?
C12 O13 C13 116.93(11) . . ?
O13 C13 C14 106.94(12) . . ?
O13 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O13 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 N C15 121.87(12) . . ?
C19 N C5 118.51(11) . . ?
C15 N C5 119.61(12) . . ?
N C15 C16 119.63(14) . . ?
N C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 119.71(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.48(13) . . ?
C16 C17 H17A 120.3 . . ?
C18 C17 H17A 120.3 . . ?
C19 C18 C17 119.48(14) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
N C19 C18 119.79(13) . . ?
N C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
H1W1 O1W H1W2 104.8(17) . . ?
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
N1 C5 1.3362(19) . ?
N1 C2 1.3655(18) . ?
C2 N3 1.3461(19) . ?
C2 C6 1.468(2) . ?
N3 C4 1.3695(18) . ?
C4 C5 1.3851(18) . ?
C4 C12 1.458(2) . ?
C5 N 1.4439(17) . ?
C6 C11 1.397(2) . ?
C6 C7 1.403(2) . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
O12 C12 1.2132(17) . ?
C12 O13 1.3415(17) . ?
O13 C13 1.4508(18) . ?
C13 C14 1.503(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N C19 1.3488(18) . ?
N C15 1.3528(18) . ?
C15 C16 1.375(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.377(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O1W H1W1 0.83(2) . ?
O1W H1W2 0.83(2) . ?
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
O1W H1W1 O12 0.83(2) 2.177(13) 2.9292(18) 150(2) .
O1W H1W2 N1 0.83(2) 2.063(11) 2.8855(17) 171(2) 3_755
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
C5 N1 C2 N3 -0.21(16) . . . . ?
C5 N1 C2 C6 177.60(12) . . . . ?
N1 C2 N3 C4 -0.02(16) . . . . ?
C6 C2 N3 C4 -177.86(12) . . . . ?
C2 N3 C4 C5 0.24(14) . . . . ?
C2 N3 C4 C12 -176.92(12) . . . . ?
C2 N1 C5 C4 0.36(15) . . . . ?
C2 N1 C5 N -176.97(12) . . . . ?
N3 C4 C5 N1 -0.40(16) . . . . ?
C12 C4 C5 N1 176.43(13) . . . . ?
N3 C4 C5 N 176.68(12) . . . . ?
C12 C4 C5 N -6.5(2) . . . . ?
N3 C2 C6 C11 172.61(13) . . . . ?
N1 C2 C6 C11 -5.1(2) . . . . ?
N3 C2 C6 C7 -5.7(2) . . . . ?
N1 C2 C6 C7 176.69(13) . . . . ?
C11 C6 C7 C8 -0.6(2) . . . . ?
C2 C6 C7 C8 177.70(13) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C6 -0.2(2) . . . . ?
C7 C6 C11 C10 0.6(2) . . . . ?
C2 C6 C11 C10 -177.71(13) . . . . ?
N3 C4 C12 O12 -2.9(2) . . . . ?
C5 C4 C12 O12 -179.33(14) . . . . ?
N3 C4 C12 O13 176.38(12) . . . . ?
C5 C4 C12 O13 0.0(2) . . . . ?
O12 C12 O13 C13 -0.8(2) . . . . ?
C4 C12 O13 C13 179.89(11) . . . . ?
C12 O13 C13 C14 179.87(12) . . . . ?
N1 C5 N C19 114.67(15) . . . . ?
C4 C5 N C19 -62.19(19) . . . . ?
N1 C5 N C15 -66.05(17) . . . . ?
C4 C5 N C15 117.08(16) . . . . ?
C19 N C15 C16 -1.5(2) . . . . ?
C5 N C15 C16 179.22(14) . . . . ?
N C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -1.8(2) . . . . ?
C15 N C19 C18 0.5(2) . . . . ?
C5 N C19 C18 179.76(13) . . . . ?
C17 C18 C19 N 1.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659104
