#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/20/4022085.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_4022085
loop_
_publ_author_name
'Vijay Nair'
'Manojkumar Poonoth'
'Sreekumar Vellalath'
'Eringathodi Suresh'
'Rajasekaran Thirumalai'
_publ_section_title
;
 An N-Heterocyclic Carbene-Catalyzed [8 + 3] Annulation of Tropone
 and Enals via Homoenolate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8964
_journal_page_last               8965
_journal_paper_doi               10.1021/jo0615706
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.191(5)
_cell_angle_beta                 103.853(5)
_cell_angle_gamma                114.504(4)
_cell_formula_units_Z            2
_cell_length_a                   7.525(2)
_cell_length_b                   8.893(3)
_cell_length_c                   11.940(3)
_cell_measurement_temperature    273(2)
_cell_volume                     678.9(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART '
_computing_data_reduction        'BRUKER SAINT '
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'Omega-PHI SCAN'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4007
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0731P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2414
_reflns_number_total             2957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0615706si20060731_043844.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.1498P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.1498P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4022085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_calc_flag
O1 O 1.02815(18) 1.07697(16) 0.28625(11) 0.0453(3) Uani 1 d
O3 O 0.3189(2) 0.67270(15) -0.03978(11) 0.0507(4) Uani 1 d
C11 C 0.4966(2) 0.7660(2) 0.16742(14) 0.0359(4) Uani 1 d
O2 O 1.0559(2) 0.91350(19) 0.14319(14) 0.0653(4) Uani 1 d
C1 C 0.7088(3) 1.0848(2) 0.27237(14) 0.0382(4) Uani 1 d
C10 C 0.6025(3) 0.9472(2) 0.15405(14) 0.0375(4) Uani 1 d
C12 C 0.3566(3) 0.6291(2) 0.06576(15) 0.0391(4) Uani 1 d
C7 C 0.9118(3) 1.1469(2) 0.32683(14) 0.0392(4) Uani 1 d
C8 C 0.9548(3) 0.9770(2) 0.17110(16) 0.0432(4) Uani 1 d
C13 C 0.2652(3) 0.4623(2) 0.07489(18) 0.0483(5) Uani 1 d
C16 C 0.5374(3) 0.7298(2) 0.27679(16) 0.0433(4) Uani 1 d
C2 C 0.5839(3) 1.1432(2) 0.32374(19) 0.0494(5) Uani 1 d
C15 C 0.4461(3) 0.5626(3) 0.28637(19) 0.0526(5) Uani 1 d
C14 C 0.3121(3) 0.4305(2) 0.1857(2) 0.0542(5) Uani 1 d
C6 C 1.0379(3) 1.2919(3) 0.43821(17) 0.0510(5) Uani 1 d
C9 C 0.7620(3) 0.9665(2) 0.09102(16) 0.0436(4) Uani 1 d
C17 C 0.1943(4) 0.5356(3) -0.14725(18) 0.0552(5) Uani 1 d
C3 C 0.6139(4) 1.1968(3) 0.4406(2) 0.0589(5) Uani 1 d
C5 C 0.9626(4) 1.2401(3) 0.53949(18) 0.0561(5) Uani 1 d
C4 C 0.7741(4) 1.2060(3) 0.53930(19) 0.0594(5) Uani 1 d
H10 H 0.493(3) 0.966(2) 0.1043(16) 0.037(4) Uiso 1 d
H16 H 0.630(3) 0.821(2) 0.3464(17) 0.043(5) Uiso 1 d
H2 H 0.474(4) 1.135(3) 0.266(2) 0.061(6) Uiso 1 d
H13 H 0.163(3) 0.370(3) 0.0050(18) 0.050(5) Uiso 1 d
H9A H 0.809(3) 1.075(3) 0.0685(17) 0.054(6) Uiso 1 d
H4 H 0.732(3) 1.180(3) 0.610(2) 0.064(6) Uiso 1 d
H17A H 0.043(4) 0.470(3) -0.1466(19) 0.060(6) Uiso 1 d
H6B H 1.013(3) 1.387(3) 0.4240(19) 0.065(7) Uiso 1 d
H6A H 1.180(4) 1.322(3) 0.4555(18) 0.053(6) Uiso 1 d
H17C H 0.254(3) 0.456(3) -0.1584(18) 0.056(6) Uiso 1 d
H9B H 0.701(3) 0.873(3) 0.0172(19) 0.053(5) Uiso 1 d
H15 H 0.487(4) 0.542(3) 0.364(2) 0.073(7) Uiso 1 d
H5 H 1.069(4) 1.234(3) 0.605(2) 0.077(7) Uiso 1 d
H17B H 0.194(4) 0.587(3) -0.213(2) 0.075(7) Uiso 1 d
H14 H 0.246(3) 0.315(3) 0.1919(18) 0.059(6) Uiso 1 d
H3 H 0.509(4) 1.216(3) 0.460(2) 0.080(8) Uiso 1 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'
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
C8 O1 C7 120.05(14)
C12 O3 C17 117.33(15)
C16 C11 C12 118.04(15)
C16 C11 C10 122.27(14)
C12 C11 C10 119.67(14)
C7 C1 C2 122.28(16)
C7 C1 C10 119.38(15)
C2 C1 C10 118.33(15)
C1 C10 C11 113.23(13)
C1 C10 C9 108.27(14)
C11 C10 C9 111.69(14)
C1 C10 H10 108.3(10)
C11 C10 H10 106.5(11)
C9 C10 H10 108.7(10)
O3 C12 C13 123.69(15)
O3 C12 C11 115.60(14)
C13 C12 C11 120.71(16)
C1 C7 O1 122.69(15)
C1 C7 C6 124.69(17)
O1 C7 C6 112.59(16)
O2 C8 O1 117.11(17)
O2 C8 C9 126.62(17)
O1 C8 C9 116.17(15)
C14 C13 C12 119.64(17)
C14 C13 H13 120.3(12)
C12 C13 H13 120.0(12)
C11 C16 C15 121.44(17)
C11 C16 H16 119.1(11)
C15 C16 H16 119.5(11)
C3 C2 C1 126.68(19)
C3 C2 H2 121.7(14)
C1 C2 H2 111.5(14)
C14 C15 C16 119.56(18)
C14 C15 H15 121.7(15)
C16 C15 H15 118.6(15)
C15 C14 C13 120.60(18)
C15 C14 H14 120.0(13)
C13 C14 H14 119.3(13)
C7 C6 C5 109.03(16)
C7 C6 H6B 107.1(13)
C5 C6 H6B 108.0(13)
C7 C6 H6A 109.9(13)
C5 C6 H6A 111.6(13)
H6B C6 H6A 111.1(19)
C8 C9 C10 112.19(14)
C8 C9 H9A 104.3(12)
C10 C9 H9A 111.1(12)
C8 C9 H9B 111.3(12)
C10 C9 H9B 110.3(12)
H9A C9 H9B 107.4(16)
O3 C17 H17A 110.1(12)
O3 C17 H17C 111.4(12)
H17A C17 H17C 111.1(17)
O3 C17 H17B 106.8(15)
H17A C17 H17B 109.6(19)
H17C C17 H17B 107.6(19)
C2 C3 C4 126.6(2)
C2 C3 H3 116.7(16)
C4 C3 H3 116.1(16)
C4 C5 C6 122.2(2)
C4 C5 H5 124.7(15)
C6 C5 H5 113.1(15)
C5 C4 C3 124.9(2)
C5 C4 H4 120.3(13)
C3 C4 H4 114.7(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.366(2)
O1 C7 1.399(2)
O3 C12 1.371(2)
O3 C17 1.429(2)
C11 C16 1.383(2)
C11 C12 1.403(2)
C11 C10 1.525(2)
O2 C8 1.197(2)
C1 C7 1.336(2)
C1 C2 1.455(3)
C1 C10 1.513(2)
C10 C9 1.528(3)
C10 H10 0.984(18)
C12 C13 1.386(2)
C7 C6 1.491(2)
C8 C9 1.492(3)
C13 C14 1.386(3)
C13 H13 0.97(2)
C16 C15 1.391(3)
C16 H16 0.95(2)
C2 C3 1.340(3)
C2 H2 0.91(2)
C15 C14 1.370(3)
C15 H15 0.97(2)
C14 H14 0.96(2)
C6 C5 1.505(3)
C6 H6B 0.97(2)
C6 H6A 0.95(2)
C9 H9A 0.98(2)
C9 H9B 0.98(2)
C17 H17A 1.04(2)
C17 H17C 0.99(2)
C17 H17B 0.96(3)
C3 C4 1.435(3)
C3 H3 0.95(3)
C5 C4 1.321(3)
C5 H5 1.00(3)
C4 H4 1.00(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10164119
