#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/62/2216239.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216239
loop_
_publ_author_name
'Yang, Chao'
'Xia, Wujiong'
'Zhang, Xiao'
'Li, Bing'
'Gou, Baoquan'
_publ_section_title
;
 Methyl 4-[(1-methylcyclopent-3-en-1-yl)carbonyl]benzoate
;
_journal_coeditor_code           BG2118
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4729
_journal_page_last               o4729
_journal_paper_doi               10.1107/S1600536807052658
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H16 O3'
_chemical_formula_moiety         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28
_chemical_name_systematic
;
Methyl 4-[(1-methylcyclopent-3-en-1-yl)carbonyl]benzoate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6215(6)
_cell_length_b                   6.6520(2)
_cell_length_c                   11.5581(5)
_cell_measurement_temperature    173(2)
_cell_volume                     1277.94(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and\ w'
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22416
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.2712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                1290
_reflns_number_total             1656
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2118.cif
_cod_data_source_block           I
_cod_database_code               2216239
_cod_database_fobs_code          2216239
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.82779(7) 0.3482(2) 0.16325(12) 0.0432(4) Uani d . 1
H H1 0.8704 0.4256 0.1362 0.052 Uiso calc R 1
C C2 0.75151(7) 0.4356(2) 0.21171(12) 0.0426(4) Uani d . 1
H H2A 0.7191 0.4960 0.1512 0.051 Uiso calc R 1
H H2B 0.7631 0.5363 0.2701 0.051 Uiso calc R 1
C C3 0.70802(10) 0.2500 0.26576(15) 0.0365(4) Uani d S 1
C C4 0.72151(14) 0.2500 0.39724(19) 0.0798(10) Uani d S 1
H H4A 0.7782 0.2500 0.4132 0.120 Uiso calc SR 1
H H4B 0.6974 0.1322 0.4303 0.120 Uiso calc PR 0.50
H H4C 0.6974 0.3678 0.4303 0.120 Uiso calc PR 0.50
C C5 0.61758(10) 0.2500 0.24182(14) 0.0274(4) Uani d S 1
C C6 0.58474(9) 0.2500 0.11956(13) 0.0226(3) Uani d S 1
C C7 0.63221(9) 0.2500 0.01907(14) 0.0263(4) Uani d S 1
H H7 0.6880 0.2500 0.0251 0.032 Uiso calc SR 1
C C8 0.59613(9) 0.2500 -0.08943(14) 0.0265(4) Uani d S 1
H H8 0.6279 0.2500 -0.1556 0.032 Uiso calc SR 1
C C9 0.51238(9) 0.2500 -0.09965(13) 0.0222(3) Uani d S 1
C C10 0.46505(9) 0.2500 -0.00022(13) 0.0237(3) Uani d S 1
H H10 0.4093 0.2500 -0.0066 0.028 Uiso calc SR 1
C C11 0.50064(9) 0.2500 0.10786(14) 0.0242(3) Uani d S 1
H H11 0.4685 0.2500 0.1737 0.029 Uiso calc SR 1
C C12 0.47066(10) 0.2500 -0.21404(13) 0.0255(3) Uani d S 1
C C13 0.48394(13) 0.2500 -0.41695(15) 0.0426(5) Uani d S 1
H H13A 0.5245 0.2500 -0.4760 0.064 Uiso calc SR 1
H H13B 0.4510 0.3678 -0.4248 0.064 Uiso calc PR 0.50
H H13C 0.4510 0.1322 -0.4248 0.064 Uiso calc PR 0.50
O O1 0.56999(7) 0.2500 0.32202(10) 0.0398(3) Uani d S 1
O O2 0.39814(7) 0.2500 -0.22520(10) 0.0359(3) Uani d S 1
O O3 0.52206(7) 0.2500 -0.30386(9) 0.0336(3) Uani d S 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 C1 C2 8_565 . 112.76(8)
C1 C1 H1 8_565 . 123.6
C2 C1 H1 . . 123.6
C1 C2 C3 . . 103.51(12)
C1 C2 H2A . . 111.1
C3 C2 H2A . . 111.1
C1 C2 H2B . . 111.1
C3 C2 H2B . . 111.1
H2A C2 H2B . . 109.0
C5 C3 C4 . . 108.82(15)
C5 C3 C2 . . 112.52(9)
C4 C3 C2 . . 109.16(10)
C5 C3 C2 . 8_565 112.52(9)
C4 C3 C2 . 8_565 109.16(10)
C2 C3 C2 . 8_565 104.54(14)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
O1 C5 C6 . . 118.40(14)
O1 C5 C3 . . 120.05(15)
C6 C5 C3 . . 121.55(14)
C7 C6 C11 . . 118.66(14)
C7 C6 C5 . . 124.69(13)
C11 C6 C5 . . 116.65(13)
C8 C7 C6 . . 120.25(13)
C8 C7 H7 . . 119.9
C6 C7 H7 . . 119.9
C7 C8 C9 . . 120.41(14)
C7 C8 H8 . . 119.8
C9 C8 H8 . . 119.8
C10 C9 C8 . . 119.54(14)
C10 C9 C12 . . 117.93(13)
C8 C9 C12 . . 122.53(14)
C11 C10 C9 . . 120.27(13)
C11 C10 H10 . . 119.9
C9 C10 H10 . . 119.9
C10 C11 C6 . . 120.87(14)
C10 C11 H11 . . 119.6
C6 C11 H11 . . 119.6
O2 C12 O3 . . 123.34(14)
O2 C12 C9 . . 123.79(14)
O3 C12 C9 . . 112.87(13)
O3 C13 H13A . . 109.5
O3 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
O3 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C12 O3 C13 . . 114.69(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C1 8_565 1.307(3)
C1 C2 . 1.5030(18)
C1 H1 . 0.9300
C2 C3 . 1.5612(17)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 C5 . 1.529(2)
C3 C4 . 1.536(3)
C3 C2 8_565 1.5612(17)
C4 H4A . 0.9600
C4 H4B . 0.9600
C4 H4C . 0.9600
C5 O1 . 1.219(2)
C5 C6 . 1.515(2)
C6 C7 . 1.404(2)
C6 C11 . 1.404(2)
C7 C8 . 1.390(2)
C7 H7 . 0.9300
C8 C9 . 1.397(2)
C8 H8 . 0.9300
C9 C10 . 1.393(2)
C9 C12 . 1.493(2)
C10 C11 . 1.382(2)
C10 H10 . 0.9300
C11 H11 . 0.9300
C12 O2 . 1.2123(19)
C12 O3 . 1.3444(19)
C13 O3 . 1.453(2)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13A O1 1_554 0.96 2.45 3.339(2) 153.3
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C1 C1 C2 C3 8_565 . 10.60(11)
C1 C2 C3 C5 . . -138.49(12)
C1 C2 C3 C4 . . 100.59(14)
C1 C2 C3 C2 . 8_565 -16.10(17)
C4 C3 C5 O1 . . 0.0
C2 C3 C5 O1 . . -121.11(10)
C2 C3 C5 O1 8_565 . 121.11(10)
C4 C3 C5 C6 . . 180.0
C2 C3 C5 C6 . . 58.89(10)
C2 C3 C5 C6 8_565 . -58.89(10)
O1 C5 C6 C7 . . 180.0
C3 C5 C6 C7 . . 0.0
O1 C5 C6 C11 . . 0.0
C3 C5 C6 C11 . . 180.0
C11 C6 C7 C8 . . 0.0
C5 C6 C7 C8 . . 180.0
C6 C7 C8 C9 . . 0.0
C7 C8 C9 C10 . . 0.0
C7 C8 C9 C12 . . 180.0
C8 C9 C10 C11 . . 0.0
C12 C9 C10 C11 . . 180.0
C9 C10 C11 C6 . . 0.0
C7 C6 C11 C10 . . 0.0
C5 C6 C11 C10 . . 180.0
C10 C9 C12 O2 . . 0.0
C8 C9 C12 O2 . . 180.0
C10 C9 C12 O3 . . 180.0
C8 C9 C12 O3 . . 0.0
O2 C12 O3 C13 . . 0.0
C9 C12 O3 C13 . . 180.0
