#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/46/2214667.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_2214667
loop_
_publ_author_name
'Dinçer, Muharrem'
'Özdemir, Namık'
'Yılmaz, İbrahim'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2-Chloro-1-(3-methyl-3-phenylcyclobutyl)ethanone
;
_journal_coeditor_code           GW2017
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3489
_journal_page_last               o3489
_journal_paper_doi               10.1107/S160053680703317X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H15 Cl O'
_chemical_formula_moiety         'C13 H15 Cl O'
_chemical_formula_sum            'C13 H15 Cl O'
_chemical_formula_weight         222.70
_chemical_name_systematic
;
2-Chloro-1-(3-methyl-3-phenylcyclobutyl)ethanone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                   9.4980(9)
_cell_length_b                   15.6393(11)
_cell_length_c                   7.8578(7)
_cell_measurement_reflns_used    6312
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.51
_cell_volume                     1167.21(17)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6736
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.9443
_exptl_absorpt_correction_T_min  0.8847
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.192
_refine_ls_abs_structure_details 'Flack (1983), 1251 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.0052(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0299
_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)+(0.0380P)²+0.0689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                2435
_reflns_number_total             2743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2017.cif
_cod_data_source_block           I
_cod_database_code               2214667
_cod_database_fobs_code          2214667
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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
Cl Cl1 0.41536(4) 0.37951(2) 0.10882(5) 0.03443(11) Uani d . 1
O O1 0.27620(14) 0.54032(7) 0.00821(18) 0.0385(3) Uani d . 1
C C1 0.43719(18) 0.47994(10) 0.2090(2) 0.0304(3) Uani d . 1
H H1A 0.4059 0.4754 0.3262 0.036 Uiso calc R 1
H H1B 0.5366 0.4940 0.2106 0.036 Uiso calc R 1
C C2 0.35801(15) 0.55188(9) 0.1242(2) 0.0243(3) Uani d . 1
C C3 0.39456(16) 0.63806(9) 0.19372(19) 0.0234(3) Uani d . 1
H H3 0.4005 0.6363 0.3182 0.028 Uiso calc R 1
C C4 0.52987(14) 0.67903(9) 0.1165(2) 0.0253(3) Uani d . 1
H H4A 0.6116 0.6759 0.1903 0.030 Uiso calc R 1
H H4B 0.5521 0.6591 0.0027 0.030 Uiso calc R 1
C C5 0.45381(14) 0.76651(9) 0.1207(2) 0.0228(3) Uani d . 1
C C6 0.31190(15) 0.71696(9) 0.13509(19) 0.0227(3) Uani d . 1
H H6A 0.2485 0.7397 0.2207 0.027 Uiso calc R 1
H H6B 0.2639 0.7093 0.0272 0.027 Uiso calc R 1
C C7 0.48815(19) 0.81500(11) 0.2856(2) 0.0278(4) Uani d . 1
H H7A 0.4785 0.7771 0.3810 0.042 Uiso calc R 1
H H7B 0.4244 0.8622 0.2984 0.042 Uiso calc R 1
H H7C 0.5830 0.8360 0.2806 0.042 Uiso calc R 1
C C8 0.46899(18) 0.82486(10) -0.03045(19) 0.0231(3) Uani d . 1
C C9 0.58479(18) 0.82191(11) -0.1395(2) 0.0285(3) Uani d . 1
H H9 0.6562 0.7825 -0.1200 0.034 Uiso calc R 1
C C10 0.5941(2) 0.87746(12) -0.2769(2) 0.0346(4) Uani d . 1
H H10 0.6713 0.8743 -0.3494 0.041 Uiso calc R 1
C C11 0.4903(2) 0.93721(11) -0.3071(2) 0.0356(4) Uani d . 1
H H11 0.4973 0.9743 -0.3992 0.043 Uiso calc R 1
C C12 0.3753(2) 0.94139(11) -0.1987(2) 0.0330(4) Uani d . 1
H H12 0.3051 0.9818 -0.2175 0.040 Uiso calc R 1
C C13 0.36494(19) 0.88556(10) -0.06253(19) 0.0263(3) Uani d . 1
H H13 0.2870 0.8886 0.0089 0.032 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C2 C1 Cl1 114.01(12) yes
C2 C1 H1A 108.7 ?
Cl1 C1 H1A 108.7 ?
C2 C1 H1B 108.7 ?
Cl1 C1 H1B 108.7 ?
H1A C1 H1B 107.6 ?
O1 C2 C3 123.96(13) yes
O1 C2 C1 122.75(14) yes
C3 C2 C1 113.26(14) ?
C2 C3 C6 119.78(13) ?
C2 C3 C4 114.81(13) ?
C6 C3 C4 88.53(11) yes
C2 C3 H3 110.6 ?
C6 C3 H3 110.6 ?
C4 C3 H3 110.6 ?
C5 C4 C3 88.29(10) yes
C5 C4 H4A 113.9 ?
C3 C4 H4A 113.9 ?
C5 C4 H4B 113.9 ?
C3 C4 H4B 113.9 ?
H4A C4 H4B 111.1 ?
C8 C5 C7 110.25(11) ?
C8 C5 C4 118.32(15) ?
C7 C5 C4 110.82(14) ?
C8 C5 C6 116.20(13) ?
C7 C5 C6 111.58(13) ?
C4 C5 C6 88.04(10) yes
C3 C6 C5 88.80(10) yes
C3 C6 H6A 113.8 ?
C5 C6 H6A 113.8 ?
C3 C6 H6B 113.8 ?
C5 C6 H6B 113.8 ?
H6A C6 H6B 111.1 ?
C5 C7 H7A 109.5 ?
C5 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C5 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C13 C8 C9 118.07(15) ?
C13 C8 C5 119.21(14) ?
C9 C8 C5 122.71(15) ?
C10 C9 C8 120.48(17) ?
C10 C9 H9 119.8 ?
C8 C9 H9 119.8 ?
C11 C10 C9 120.80(17) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 119.31(16) ?
C10 C11 H11 120.3 ?
C12 C11 H11 120.3 ?
C13 C12 C11 120.08(18) ?
C13 C12 H12 120.0 ?
C11 C12 H12 120.0 ?
C12 C13 C8 121.26(16) ?
C12 C13 H13 119.4 ?
C8 C13 H13 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.7692(17) yes
O1 C2 1.211(2) yes
C1 C2 1.509(2) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C3 1.495(2) ?
C3 C6 1.5334(19) yes
C3 C4 1.559(2) yes
C3 H3 0.9800 ?
C4 C5 1.5475(19) yes
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C8 1.505(2) ?
C5 C7 1.536(2) ?
C5 C6 1.5589(19) yes
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C13 1.393(2) ?
C8 C9 1.395(2) ?
C9 C10 1.388(2) ?
C9 H9 0.9300 ?
C10 C11 1.379(3) ?
C10 H10 0.9300 ?
C11 C12 1.386(3) ?
C11 H11 0.9300 ?
C12 C13 1.385(2) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
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
C1 H1A O1 3 0.97 2.46 3.244(2) 137.4
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_publ_flag
Cl1 C1 C2 O1 6.8(2) yes
Cl1 C1 C2 C3 -171.24(11) yes
O1 C2 C3 C6 8.6(2) ?
C1 C2 C3 C6 -173.33(13) ?
O1 C2 C3 C4 -94.80(19) ?
C1 C2 C3 C4 83.25(17) ?
C2 C3 C4 C5 141.38(13) ?
C6 C3 C4 C5 19.00(12) ?
C3 C4 C5 C8 -137.59(13) ?
C3 C4 C5 C7 93.69(14) ?
C3 C4 C5 C6 -18.69(12) ?
C2 C3 C6 C5 -136.82(14) ?
C4 C3 C6 C5 -18.86(12) ?
C8 C5 C6 C3 139.81(13) ?
C7 C5 C6 C3 -92.64(13) ?
C4 C5 C6 C3 19.01(13) ?
C7 C5 C8 C13 -75.72(17) ?
C4 C5 C8 C13 155.30(13) ?
C6 C5 C8 C13 52.5(2) ?
C7 C5 C8 C9 103.18(17) ?
C4 C5 C8 C9 -25.8(2) ?
C6 C5 C8 C9 -128.62(16) ?
C13 C8 C9 C10 -0.8(2) ?
C5 C8 C9 C10 -179.69(15) ?
C8 C9 C10 C11 0.8(3) ?
C9 C10 C11 C12 -0.1(3) ?
C10 C11 C12 C13 -0.5(3) ?
C11 C12 C13 C8 0.5(2) ?
C9 C8 C13 C12 0.2(2) ?
C5 C8 C13 C12 179.10(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123846
