#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:42:25 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238616 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/54/1555402.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_1555402
loop_
_publ_author_name
'Arunprasath, Dhanarajan'
'Muthupandi, Pandi'
'Sekar, Govindasamy'
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Carbene Insertion Prior to
 Intramolecular Heck Cyclization: Synthesis of
 2-Arylidene-3-aryl-1-indanones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5448
_journal_page_last               5451
_journal_paper_doi               10.1021/acs.orglett.5b02803
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C22 H15 Cl O'
_chemical_formula_sum            'C22 H15 Cl O'
_chemical_formula_weight         330.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                92.224(2)
_cell_angle_beta                 101.2532(19)
_cell_angle_gamma                92.809(2)
_cell_formula_units_Z            2
_cell_length_a                   6.5461(2)
_cell_length_b                   8.9980(4)
_cell_length_c                   14.2101(5)
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.27
_cell_volume                     818.92(5)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9903
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.463
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       Block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0354
_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)+(0.0364P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b02803_si_003.cif
_cod_data_source_block           157
_cod_database_code               1555402
_shelx_shelxl_version_number     2014/7
_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   0.943
_shelx_estimated_absorpt_t_max   0.972
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 0.3410(3) 0.58587(19) 0.10001(12) 0.0492(4) Uani 1 1 d . .
H1 H 0.1995 0.5572 0.0843 0.059 Uiso 1 1 calc R U
C2 C 0.4334(4) 0.6725(2) 0.03982(13) 0.0593(5) Uani 1 1 d . .
H2 H 0.3523 0.7017 -0.0170 0.071 Uiso 1 1 calc R U
C3 C 0.6435(4) 0.7169(2) 0.06192(14) 0.0608(5) Uani 1 1 d . .
H3 H 0.7014 0.7750 0.0200 0.073 Uiso 1 1 calc R U
C4 C 0.7668(3) 0.6755(2) 0.14538(14) 0.0546(5) Uani 1 1 d . .
H4 H 0.9079 0.7051 0.1609 0.066 Uiso 1 1 calc R U
C5 C 0.6743(3) 0.58810(18) 0.20607(12) 0.0424(4) Uani 1 1 d . .
C6 C 0.7720(2) 0.52944(18) 0.29832(12) 0.0413(4) Uani 1 1 d . .
C7 C 0.6053(2) 0.44377(18) 0.33449(11) 0.0367(4) Uani 1 1 d . .
C8 C 0.4031(2) 0.44412(17) 0.26022(10) 0.0364(4) Uani 1 1 d . .
H8 H 0.2959 0.4906 0.2889 0.044 Uiso 1 1 calc R U
C9 C 0.4644(3) 0.54261(17) 0.18452(11) 0.0388(4) Uani 1 1 d . .
C10 C 0.6512(2) 0.38432(18) 0.42037(11) 0.0406(4) Uani 1 1 d . .
H10 H 0.7900 0.4010 0.4511 0.049 Uiso 1 1 calc R U
C11 C 0.5242(2) 0.29843(18) 0.47469(11) 0.0390(4) Uani 1 1 d . .
C12 C 0.6240(3) 0.2380(2) 0.55938(12) 0.0500(4) Uani 1 1 d . .
H12 H 0.7681 0.2525 0.5781 0.060 Uiso 1 1 calc R U
C13 C 0.5153(3) 0.1578(2) 0.61600(13) 0.0542(5) Uani 1 1 d . .
H13 H 0.5851 0.1176 0.6718 0.065 Uiso 1 1 calc R U
C14 C 0.3015(3) 0.13778(19) 0.58882(12) 0.0448(4) Uani 1 1 d . .
C15 C 0.1974(3) 0.1966(2) 0.50605(12) 0.0463(4) Uani 1 1 d . .
H15 H 0.0531 0.1828 0.4884 0.056 Uiso 1 1 calc R U
C16 C 0.3073(2) 0.2758(2) 0.44974(11) 0.0441(4) Uani 1 1 d . .
H16 H 0.2360 0.3151 0.3939 0.053 Uiso 1 1 calc R U
C17 C 0.3199(2) 0.29103(17) 0.21499(10) 0.0350(3) Uani 1 1 d . .
C18 C 0.4533(3) 0.18306(19) 0.19968(12) 0.0434(4) Uani 1 1 d . .
H18 H 0.5964 0.2022 0.2200 0.052 Uiso 1 1 calc R U
C19 C 0.3788(3) 0.0466(2) 0.15461(13) 0.0515(5) Uani 1 1 d . .
H19 H 0.4716 -0.0247 0.1447 0.062 Uiso 1 1 calc R U
C20 C 0.1676(3) 0.0163(2) 0.12437(12) 0.0534(5) Uani 1 1 d . .
H20 H 0.1170 -0.0752 0.0938 0.064 Uiso 1 1 calc R U
C21 C 0.0320(3) 0.1223(2) 0.13965(13) 0.0577(5) Uani 1 1 d . .
H21 H -0.1111 0.1021 0.1200 0.069 Uiso 1 1 calc R U
C22 C 0.1072(3) 0.2592(2) 0.18418(13) 0.0500(4) Uani 1 1 d . .
H22 H 0.0142 0.3306 0.1936 0.060 Uiso 1 1 calc R U
Cl1 Cl 0.15916(8) 0.04191(6) 0.66094(3) 0.06340(18) Uani 1 1 d . .
O1 O 0.95620(18) 0.54573(15) 0.33717(9) 0.0572(3) 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'
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 C9 118.49(18)
C2 C1 H1 120.8
C9 C1 H1 120.8
C1 C2 C3 121.71(18)
C1 C2 H2 119.1
C3 C2 H2 119.1
C4 C3 C2 120.37(18)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 118.08(18)
C3 C4 H4 121.0
C5 C4 H4 121.0
C9 C5 C4 122.04(16)
C9 C5 C6 109.56(14)
C4 C5 C6 128.40(16)
O1 C6 C5 126.49(16)
O1 C6 C7 126.42(16)
C5 C6 C7 107.08(13)
C10 C7 C6 119.20(14)
C10 C7 C8 132.13(15)
C6 C7 C8 108.67(13)
C9 C8 C7 102.61(12)
C9 C8 C17 110.08(12)
C7 C8 C17 114.68(13)
C9 C8 H8 109.7
C7 C8 H8 109.7
C17 C8 H8 109.7
C5 C9 C1 119.32(16)
C5 C9 C8 111.96(14)
C1 C9 C8 128.70(15)
C7 C10 C11 131.92(15)
C7 C10 H10 114.0
C11 C10 H10 114.0
C12 C11 C16 117.27(15)
C12 C11 C10 118.13(14)
C16 C11 C10 124.57(14)
C13 C12 C11 121.92(16)
C13 C12 H12 119.0
C11 C12 H12 119.0
C12 C13 C14 119.02(16)
C12 C13 H13 120.5
C14 C13 H13 120.5
C15 C14 C13 120.72(16)
C15 C14 Cl1 119.20(13)
C13 C14 Cl1 120.05(13)
C16 C15 C14 119.84(16)
C16 C15 H15 120.1
C14 C15 H15 120.1
C15 C16 C11 121.23(15)
C15 C16 H16 119.4
C11 C16 H16 119.4
C18 C17 C22 118.10(15)
C18 C17 C8 121.15(13)
C22 C17 C8 120.68(14)
C17 C18 C19 121.29(16)
C17 C18 H18 119.4
C19 C18 H18 119.4
C20 C19 C18 120.10(17)
C20 C19 H19 119.9
C18 C19 H19 119.9
C21 C20 C19 119.43(17)
C21 C20 H20 120.3
C19 C20 H20 120.3
C20 C21 C22 120.31(17)
C20 C21 H21 119.8
C22 C21 H21 119.8
C21 C22 C17 120.76(17)
C21 C22 H22 119.6
C17 C22 H22 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(3)
C1 C9 1.391(2)
C1 H1 0.9300
C2 C3 1.385(3)
C2 H2 0.9300
C3 C4 1.373(3)
C3 H3 0.9300
C4 C5 1.392(2)
C4 H4 0.9300
C5 C9 1.386(2)
C5 C6 1.472(2)
C6 O1 1.2233(19)
C6 C7 1.489(2)
C7 C10 1.338(2)
C7 C8 1.524(2)
C8 C9 1.520(2)
C8 C17 1.526(2)
C8 H8 0.9800
C10 C11 1.455(2)
C10 H10 0.9300
C11 C12 1.396(2)
C11 C16 1.398(2)
C12 C13 1.376(3)
C12 H12 0.9300
C13 C14 1.378(2)
C13 H13 0.9300
C14 C15 1.378(2)
C14 Cl1 1.7393(18)
C15 C16 1.372(2)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.376(2)
C17 C22 1.388(2)
C18 C19 1.383(2)
C18 H18 0.9300
C19 C20 1.376(3)
C19 H19 0.9300
C20 C21 1.374(3)
C20 H20 0.9300
C21 C22 1.385(2)
C21 H21 0.9300
C22 H22 0.9300
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
C9 C1 C2 C3 -0.2(3)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C9 0.0(3)
C3 C4 C5 C6 179.71(16)
C9 C5 C6 O1 178.18(16)
C4 C5 C6 O1 -1.5(3)
C9 C5 C6 C7 -0.65(17)
C4 C5 C6 C7 179.63(16)
O1 C6 C7 C10 4.4(3)
C5 C6 C7 C10 -176.76(14)
O1 C6 C7 C8 -176.15(15)
C5 C6 C7 C8 2.68(16)
C10 C7 C8 C9 175.87(17)
C6 C7 C8 C9 -3.46(15)
C10 C7 C8 C17 -64.8(2)
C6 C7 C8 C17 115.88(14)
C4 C5 C9 C1 -0.3(2)
C6 C5 C9 C1 179.91(14)
C4 C5 C9 C8 178.07(14)
C6 C5 C9 C8 -1.68(18)
C2 C1 C9 C5 0.4(2)
C2 C1 C9 C8 -177.67(16)
C7 C8 C9 C5 3.19(16)
C17 C8 C9 C5 -119.32(14)
C7 C8 C9 C1 -178.59(15)
C17 C8 C9 C1 58.9(2)
C6 C7 C10 C11 178.98(15)
C8 C7 C10 C11 -0.3(3)
C7 C10 C11 C12 173.42(17)
C7 C10 C11 C16 -8.7(3)
C16 C11 C12 C13 0.8(3)
C10 C11 C12 C13 178.77(17)
C11 C12 C13 C14 -0.7(3)
C12 C13 C14 C15 0.2(3)
C12 C13 C14 Cl1 -177.95(14)
C13 C14 C15 C16 0.2(3)
Cl1 C14 C15 C16 178.35(13)
C14 C15 C16 C11 -0.1(3)
C12 C11 C16 C15 -0.4(2)
C10 C11 C16 C15 -178.22(16)
C9 C8 C17 C18 81.69(18)
C7 C8 C17 C18 -33.4(2)
C9 C8 C17 C22 -95.42(17)
C7 C8 C17 C22 149.51(15)
C22 C17 C18 C19 0.2(2)
C8 C17 C18 C19 -176.93(15)
C17 C18 C19 C20 -0.2(3)
C18 C19 C20 C21 -0.2(3)
C19 C20 C21 C22 0.7(3)
C20 C21 C22 C17 -0.7(3)
C18 C17 C22 C21 0.2(3)
C8 C17 C22 C21 177.41(16)
