#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154165.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_7154165
loop_
_publ_author_name
'Raveendra Babu, Kaki'
'Khan, Faiz Ahmed'
_publ_section_title
;
 A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl
 alcohols leading to indenones and a de novo synthesis of ninhydrin
 derivatives.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              299
_journal_page_last               308
_journal_paper_doi               10.1039/c4ob01977f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C20 H12 Cl4 O2'
_chemical_formula_sum            'C20 H12 Cl4 O2'
_chemical_formula_weight         426.10
_chemical_name_systematic        '2,3-Dichloro-5-methyl-1H-inden-1-one '
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 130.63(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.378(3)
_cell_length_b                   8.8145(3)
_cell_length_c                   14.806(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1820.3(9)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.980
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3396
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.518
_diffrn_reflns_theta_min         5.874
_exptl_absorpt_coefficient_mu    6.015
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0465
_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)+(0.0764P)²+0.8646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1359
_reflns_number_total             1717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob01977f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7154165.cif.'
_cod_database_code               7154165
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl2 Cl 0.10568(7) 0.10972(8) 0.46538(7) 0.0893(4) Uani 1 1 d . .
Cl1 Cl 0.11336(8) 0.16109(9) 0.25401(8) 0.0981(4) Uani 1 1 d . .
C5 C 0.1241(2) -0.2491(3) 0.3496(2) 0.0644(7) Uani 1 1 d . .
O1 O 0.15024(18) -0.1656(3) 0.21732(19) 0.0832(7) Uani 1 1 d . .
C8 C 0.1244(2) -0.4027(3) 0.5128(3) 0.0692(7) Uani 1 1 d . .
C4 C 0.0868(2) -0.1814(3) 0.3962(2) 0.0637(7) Uani 1 1 d . .
C9 C 0.0871(2) -0.2573(3) 0.4783(2) 0.0675(7) Uani 1 1 d . .
H6 H 0.0624 -0.2112 0.5098 0.081 Uiso 1 1 calc R U
C7 C 0.1600(2) -0.4708(3) 0.4630(3) 0.0738(8) Uani 1 1 d . .
H12 H 0.1837 -0.5693 0.4850 0.089 Uiso 1 1 calc R U
C3 C 0.0497(3) -0.0232(3) 0.3475(2) 0.0706(8) Uani 1 1 d . .
C6 C 0.1606(2) -0.3950(3) 0.3823(3) 0.0714(8) Uani 1 1 d . .
H9 H 0.1850 -0.4409 0.3504 0.086 Uiso 1 1 calc R U
C2 C 0.0631(3) -0.0070(3) 0.2538(3) 0.0717(8) Uani 1 1 d . .
C10 C 0.1293(3) -0.4858(4) 0.6057(3) 0.0865(10) Uani 1 1 d . .
H8AA H 0.1918 -0.4728 0.6823 0.130 Uiso 1 1 calc R U
H8AB H 0.1174 -0.5918 0.5864 0.130 Uiso 1 1 calc R U
H8AC H 0.0818 -0.4457 0.6077 0.130 Uiso 1 1 calc R U
C1 C 0.1194(2) -0.1471(3) 0.2677(2) 0.0694(8) 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C5 C4 120.7(2) . .
C6 C5 C1 127.8(3) . .
C4 C5 C1 111.5(2) . .
C9 C8 C7 119.5(2) . .
C9 C8 C10 120.4(3) . .
C7 C8 C10 120.1(3) . .
C9 C4 C5 120.6(3) . .
C9 C4 C3 127.4(3) . .
C5 C4 C3 112.0(2) . .
C4 C9 C8 119.3(3) . .
C4 C9 H6 120.4 . .
C8 C9 H6 120.4 . .
C6 C7 C8 121.3(3) . .
C6 C7 H12 119.3 . .
C8 C7 H12 119.3 . .
C4 C3 C2 103.0(2) . .
C4 C3 C2 116.0(2) . 2
C2 C3 C2 90.9(2) . 2
C4 C3 Cl2 110.3(2) . .
C2 C3 Cl2 119.2(2) . .
C2 C3 Cl2 115.78(19) 2 .
C7 C6 C5 118.7(3) . .
C7 C6 H9 120.7 . .
C5 C6 H9 120.7 . .
C1 C2 C3 106.8(2) . .
C1 C2 C3 113.9(2) . 2
C3 C2 C3 88.1(2) . 2
C1 C2 Cl1 111.8(2) . .
C3 C2 Cl1 117.69(18) . .
C3 C2 Cl1 116.27(19) 2 .
C8 C10 H8AA 109.5 . .
C8 C10 H8AB 109.5 . .
H8AA C10 H8AB 109.5 . .
C8 C10 H8AC 109.5 . .
H8AA C10 H8AC 109.5 . .
H8AB C10 H8AC 109.5 . .
O1 C1 C5 129.1(3) . .
O1 C1 C2 125.0(3) . .
C5 C1 C2 106.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl2 C3 1.772(3) .
Cl1 C2 1.745(3) .
C5 C6 1.384(4) .
C5 C4 1.386(4) .
C5 C1 1.467(4) .
O1 C1 1.206(3) .
C8 C9 1.385(4) .
C8 C7 1.399(4) .
C8 C10 1.509(4) .
C4 C9 1.383(3) .
C4 C3 1.513(4) .
C9 H6 0.9300 .
C7 C6 1.375(4) .
C7 H12 0.9300 .
C3 C2 1.564(3) .
C3 C2 1.586(5) 2
C6 H9 0.9300 .
C2 C1 1.537(4) .
C2 C3 1.586(5) 2
C10 H8AA 0.9600 .
C10 H8AB 0.9600 .
C10 H8AC 0.9600 .
