#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/97/4119747.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_4119747
loop_
_publ_author_name
'Yvonne Schmidt'
'Jonathan K. Lam'
'Hung V. Pham'
'K. N. Houk'
'Christopher D. Vanderwal'
_publ_section_title
;
 Studies on the Himbert Intramolecular Arene/Allene Diels-Alder
 Cycloaddition. Mechanistic Studies and Expansion of Scope to All-Carbon
 Tethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7339
_journal_page_last               7348
_journal_paper_doi               10.1021/ja4025963
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C15 H14 Cl2 O'
_chemical_formula_weight         281.16
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   dimap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                68.4580(7)
_cell_angle_beta                 64.6209(7)
_cell_angle_gamma                82.3832(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7211(6)
_cell_length_b                   9.0859(6)
_cell_length_c                   9.9538(7)
_cell_measurement_reflns_used    5933
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.41
_cell_volume                     662.54(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.914
_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  0.0119
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7631
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         2.411
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.224
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0393P)²+0.2445P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2833
_reflns_number_total             3016
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja4025963_si_003.cif
_cod_data_source_block           cdv26
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4119747
_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   0.818
_shelx_estimated_absorpt_t_max   0.901
_shelxl_version_number           2012-6
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
Cl1 Cl 1.00666(3) 1.08335(3) 0.18216(3) 0.02402(9) Uani 1 1 d
Cl2 Cl 0.49772(4) 0.61307(4) 0.18026(4) 0.02690(9) Uani 1 1 d
O1 O 0.69069(11) 1.21386(10) 0.10615(11) 0.0271(2) Uani 1 1 d
C1 C 0.58986(14) 0.94692(13) 0.17145(13) 0.0181(2) Uani 1 1 d
C2 C 0.70440(14) 1.07154(13) 0.15452(13) 0.0193(2) Uani 1 1 d
C3 C 0.83689(13) 0.98474(13) 0.20485(13) 0.0187(2) Uani 1 1 d
C4 C 0.80535(14) 0.82888(13) 0.26730(13) 0.0185(2) Uani 1 1 d
C5 C 0.91033(15) 0.69664(14) 0.31864(15) 0.0223(2) Uani 1 1 d
C6 C 0.63669(14) 0.78899(13) 0.27536(13) 0.0174(2) Uani 1 1 d
C7 C 1.17977(19) 0.39441(18) 0.2262(2) 0.0345(3) Uani 1 1 d
C8 C 1.02190(17) 0.43731(14) 0.29088(16) 0.0263(3) Uani 1 1 d
C9 C 0.95385(15) 0.59154(13) 0.21559(14) 0.0205(2) Uani 1 1 d
C10 C 0.80261(15) 0.56596(14) 0.18931(13) 0.0205(2) Uani 1 1 d
C11 C 0.66596(14) 0.65357(13) 0.21383(13) 0.0191(2) Uani 1 1 d
C12 C 0.50792(15) 0.73884(14) 0.44736(13) 0.0209(2) Uani 1 1 d
C13 C 0.37494(15) 0.82239(15) 0.50381(14) 0.0232(2) Uani 1 1 d
C14 C 0.32899(15) 0.97496(15) 0.40410(15) 0.0248(2) Uani 1 1 d
C15 C 0.40260(15) 0.98725(15) 0.23077(14) 0.0215(2) Uani 1 1 d
H1A H 0.6281(19) 0.9452(18) 0.0648(18) 0.026(4) Uiso 1 1 d
H5A H 0.8484(19) 0.6322(18) 0.4284(19) 0.024(4) Uiso 1 1 d
H5B H 1.012(2) 0.7349(19) 0.3117(18) 0.031(4) Uiso 1 1 d
H7A H 1.259(2) 0.463(2) 0.124(2) 0.045(5) Uiso 1 1 d
H7B H 1.218(2) 0.299(2) 0.279(2) 0.049(5) Uiso 1 1 d
H8A H 0.942(2) 0.371(2) 0.392(2) 0.034(4) Uiso 1 1 d
H9A H 1.0432(19) 0.6440(17) 0.1141(18) 0.025(4) Uiso 1 1 d
H10A H 0.8088(19) 0.4838(18) 0.1494(18) 0.028(4) Uiso 1 1 d
H12A H 0.5319(19) 0.6418(19) 0.5155(18) 0.027(4) Uiso 1 1 d
H13A H 0.3037(19) 0.7839(18) 0.6144(19) 0.028(4) Uiso 1 1 d
H14A H 0.373(2) 1.0657(19) 0.4145(19) 0.030(4) Uiso 1 1 d
H14B H 0.204(2) 0.983(2) 0.447(2) 0.038(4) Uiso 1 1 d
H15A H 0.343(2) 0.914(2) 0.2218(19) 0.032(4) Uiso 1 1 d
H15B H 0.3921(18) 1.0929(18) 0.1639(18) 0.024(4) Uiso 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C15 113.29(9)
C2 C1 C6 104.37(9)
C15 C1 C6 116.17(9)
O1 C2 C3 127.01(11)
O1 C2 C1 126.58(11)
C3 C2 C1 106.39(9)
C4 C3 C2 111.82(10)
C4 C3 Cl1 127.10(9)
C2 C3 Cl1 121.08(9)
C3 C4 C5 130.43(11)
C3 C4 C6 111.11(10)
C5 C4 C6 118.37(10)
C4 C5 C9 109.01(9)
C11 C6 C12 110.22(9)
C11 C6 C4 107.39(9)
C12 C6 C4 108.57(9)
C11 C6 C1 114.71(9)
C12 C6 C1 111.91(9)
C4 C6 C1 103.58(9)
C7 C8 C9 123.49(13)
C8 C9 C10 111.83(10)
C8 C9 C5 109.41(10)
C10 C9 C5 111.60(10)
C11 C10 C9 123.98(11)
C10 C11 C6 125.40(10)
C10 C11 Cl2 120.18(9)
C6 C11 Cl2 114.39(8)
C13 C12 C6 124.32(11)
C12 C13 C14 124.00(11)
C13 C14 C15 111.15(10)
C1 C15 C14 111.62(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7212(11)
Cl2 C11 1.7475(11)
O1 C2 1.2122(14)
C1 C2 1.5244(16)
C1 C15 1.5244(15)
C1 C6 1.5532(15)
C2 C3 1.4739(16)
C3 C4 1.3333(16)
C4 C5 1.4838(16)
C4 C6 1.5232(15)
C5 C9 1.5484(16)
C6 C11 1.5133(15)
C6 C12 1.5214(15)
C7 C8 1.3206(19)
C8 C9 1.5057(16)
C9 C10 1.5112(16)
C10 C11 1.3249(17)
C12 C13 1.3260(17)
C13 C14 1.5002(18)
C14 C15 1.5262(16)
