#------------------------------------------------------------------------------
#$Date: 2017-02-04 16:14:36 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191746 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/53/7155326.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_7155326
loop_
_publ_author_name
'Vayer, Marie'
'Fang, Weizhen'
'Guillot, Régis'
'Bezzenine-Lafollée, Sophie'
'Bour, Christophe'
'Gandon, Vincent'
_publ_section_title
;
 Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              584
_journal_page_last               588
_journal_paper_doi               10.1039/c6ob02122k
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C14 H22 O3'
_chemical_formula_sum            'C14 H22 O3'
_chemical_formula_weight         238.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-02 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                93.901(11)
_cell_angle_beta                 95.455(10)
_cell_angle_gamma                106.130(10)
_cell_formula_units_Z            2
_cell_length_a                   5.704(2)
_cell_length_b                   6.297(3)
_cell_length_c                   18.887(9)
_cell_measurement_reflns_used    1244
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      3.38
_cell_volume                     645.6(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9528
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.517
_diffrn_reflns_theta_min         2.177
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0788
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1969
_reflns_number_total             3599
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob02122k2.cif
_cod_data_source_block           17
_cod_depositor_comments
'Adding full bibliography for 7155325--7155326.cif.'
_cod_database_code               7155326
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.5497(4) 1.2783(4) 0.36417(13) 0.0203(5) Uani 1 1 d . .
C2 C 0.7020(4) 1.2141(4) 0.30877(13) 0.0199(5) Uani 1 1 d . .
H2A H 0.7613 1.0923 0.3239 0.024 Uiso 1 1 calc R U
H2B H 0.8436 1.3393 0.3053 0.024 Uiso 1 1 calc R U
C3 C 0.5507(4) 1.1449(4) 0.23565(13) 0.0176(5) Uani 1 1 d . .
H3 H 0.5000 1.2726 0.2202 0.021 Uiso 1 1 calc R U
C4 C 0.6889(4) 1.0700(4) 0.17837(13) 0.0203(5) Uani 1 1 d . .
H4A H 0.7500 0.9491 0.1936 0.024 Uiso 1 1 calc R U
H4B H 0.8281 1.1920 0.1706 0.024 Uiso 1 1 calc R U
C5 C 0.5141(4) 0.9931(4) 0.10929(13) 0.0209(5) Uani 1 1 d . .
H5A H 0.6051 0.9571 0.0716 0.025 Uiso 1 1 calc R U
H5B H 0.4506 1.1141 0.0956 0.025 Uiso 1 1 calc R U
C6 C 0.2972(4) 0.7892(4) 0.11608(13) 0.0197(5) Uani 1 1 d . .
C7 C 0.2103(4) 0.8016(4) 0.18885(13) 0.0170(5) Uani 1 1 d . .
C8 C 0.3223(4) 0.9615(4) 0.24344(12) 0.0157(5) Uani 1 1 d . .
C9 C 0.2245(4) 0.9436(4) 0.31190(13) 0.0179(5) Uani 1 1 d . .
C10 C 0.0824(5) 0.7793(5) 0.05897(14) 0.0267(6) Uani 1 1 d . .
H10A H -0.0511 0.6497 0.0624 0.040 Uiso 1 1 calc R U
H10B H 0.1356 0.7724 0.0124 0.040 Uiso 1 1 calc R U
H10C H 0.0286 0.9098 0.0665 0.040 Uiso 1 1 calc R U
C11 C 0.3738(5) 0.5742(4) 0.10576(14) 0.0241(6) Uani 1 1 d . .
H11A H 0.5153 0.5837 0.1390 0.036 Uiso 1 1 calc R U
H11B H 0.4130 0.5550 0.0579 0.036 Uiso 1 1 calc R U
H11C H 0.2409 0.4497 0.1140 0.036 Uiso 1 1 calc R U
C12 C 0.4526(5) 1.4738(4) 0.34713(14) 0.0251(6) Uani 1 1 d . .
H12A H 0.3449 1.4357 0.3030 0.038 Uiso 1 1 calc R U
H12B H 0.5878 1.6009 0.3426 0.038 Uiso 1 1 calc R U
H12C H 0.3637 1.5078 0.3850 0.038 Uiso 1 1 calc R U
C13 C 0.6860(5) 1.3227(5) 0.43957(14) 0.0257(6) Uani 1 1 d . .
H13A H 0.5734 1.3451 0.4728 0.031 Uiso 1 1 calc R U
H13B H 0.8180 1.4598 0.4424 0.031 Uiso 1 1 calc R U
C14 C 0.7952(5) 1.1395(5) 0.46390(15) 0.0296(6) Uani 1 1 d . .
H14A H 0.6756 0.9974 0.4516 0.044 Uiso 1 1 calc R U
H14B H 0.8398 1.1627 0.5147 0.044 Uiso 1 1 calc R U
H14C H 0.9385 1.1435 0.4406 0.044 Uiso 1 1 calc R U
O1 O 0.0112(3) 0.6339(3) 0.19546(9) 0.0223(4) Uani 1 1 d . .
H1 H -0.0351 0.6519 0.2346 0.034 Uiso 1 1 calc R U
O2 O 0.0377(3) 0.7943(3) 0.32123(9) 0.0221(4) Uani 1 1 d . .
O3 O 0.3329(3) 1.0857(3) 0.36847(9) 0.0205(4) Uani 1 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
O3 C1 C2 108.80(19)
O3 C1 C12 107.05(18)
C2 C1 C12 114.2(2)
O3 C1 C13 104.03(19)
C2 C1 C13 112.5(2)
C12 C1 C13 109.7(2)
C1 C2 C3 111.15(19)
C8 C3 C4 110.0(2)
C8 C3 C2 108.42(19)
C4 C3 C2 113.9(2)
C3 C4 C5 108.78(19)
C4 C5 C6 112.9(2)
C7 C6 C5 110.9(2)
C7 C6 C10 108.6(2)
C5 C6 C10 109.6(2)
C7 C6 C11 108.2(2)
C5 C6 C11 110.51(19)
C10 C6 C11 109.0(2)
O1 C7 C8 122.6(2)
O1 C7 C6 112.8(2)
C8 C7 C6 124.6(2)
C7 C8 C9 118.1(2)
C7 C8 C3 121.8(2)
C9 C8 C3 120.0(2)
O2 C9 O3 116.2(2)
O2 C9 C8 122.5(2)
O3 C9 C8 121.3(2)
C1 C13 C14 115.4(2)
C9 O3 C1 121.95(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O3 1.485(3)
C1 C2 1.524(3)
C1 C12 1.525(4)
C1 C13 1.525(4)
C2 C3 1.525(3)
C3 C8 1.509(3)
C3 C4 1.521(3)
C4 C5 1.526(3)
C5 C6 1.538(3)
C6 C7 1.509(3)
C6 C10 1.538(3)
C6 C11 1.540(4)
C7 O1 1.341(3)
C7 C8 1.364(3)
C8 C9 1.455(3)
C9 O2 1.246(3)
C9 O3 1.327(3)
C13 C14 1.532(4)
