#------------------------------------------------------------------------------
#$Date: 2019-11-07 23:44:46 +0200 (Thu, 07 Nov 2019) $
#$Revision: 224095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/95/7049514.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_7049514
loop_
_publ_author_name
'Bartalucci, Niccolò'
'Marchetti, Fabio'
'Zacchini, Stefano'
'Pampaloni, Guido'
_publ_section_title
;
 Decarbonylation of phenylacetic acids by high valent transition metal
 halides.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5725
_journal_page_last               5734
_journal_paper_doi               10.1039/c9dt00551j
_journal_volume                  48
_journal_year                    2019
_chemical_formula_sum            'C19 H15 Cl4 Mo O'
_chemical_formula_weight         497.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-01-18 deposited with the CCDC.    2019-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.547(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9934(15)
_cell_length_b                   19.335(3)
_cell_length_c                   11.3379(19)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.726
_cell_measurement_theta_min      2.521
_cell_volume                     1949.6(6)
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21352
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         2.100
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  0.3347
_exptl_absorpt_correction_T_min  0.1948
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.15280 (selected reflections only, before parameter refinement)
 R(int) =  0.0403(selected reflections only, after parameter refinement)
;
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_description       prism
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0252P)²+1.4733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0560
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4088
_reflns_number_total             4254
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt00551j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7049514--7049520.cif.'
_cod_database_code               7049514
_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   0.774
_shelx_estimated_absorpt_t_max   0.867
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.61038(19) 0.27232(9) 0.41660(15) 0.0140(3) Uani 1 1 d . .
C2 C 0.66739(19) 0.20413(9) 0.44966(15) 0.0142(3) Uani 1 1 d . .
C3 C 0.73536(19) 0.16482(9) 0.36762(16) 0.0162(3) Uani 1 1 d . .
H3 H 0.7483 0.1844 0.2930 0.019 Uiso 1 1 calc R U
C4 C 0.7834(2) 0.09792(9) 0.39492(17) 0.0195(4) Uani 1 1 d . .
H4 H 0.8266 0.0712 0.3384 0.023 Uiso 1 1 calc R U
C5 C 0.7680(2) 0.06996(9) 0.50552(17) 0.0196(4) Uani 1 1 d . .
H5 H 0.8004 0.0240 0.5242 0.024 Uiso 1 1 calc R U
C6 C 0.7054(2) 0.10902(9) 0.58932(16) 0.0176(4) Uani 1 1 d . .
H6 H 0.6980 0.0899 0.6654 0.021 Uiso 1 1 calc R U
C7 C 0.65435(19) 0.17514(9) 0.56204(15) 0.0149(3) Uani 1 1 d . .
H7 H 0.6103 0.2012 0.6189 0.018 Uiso 1 1 calc R U
C8 C 0.6860(2) 0.31434(9) 0.33712(15) 0.0150(3) Uani 1 1 d . .
C9 C 0.8447(2) 0.31612(9) 0.35178(16) 0.0172(3) Uani 1 1 d . .
H9 H 0.9018 0.2873 0.4095 0.021 Uiso 1 1 calc R U
C10 C 0.9169(2) 0.35983(10) 0.28199(17) 0.0203(4) Uani 1 1 d . .
H10 H 1.0235 0.3627 0.2946 0.024 Uiso 1 1 calc R U
C11 C 0.8340(2) 0.39963(10) 0.19347(18) 0.0229(4) Uani 1 1 d . .
H11 H 0.8842 0.4292 0.1453 0.027 Uiso 1 1 calc R U
C12 C 0.6775(2) 0.39620(10) 0.17517(17) 0.0225(4) Uani 1 1 d . .
H12 H 0.6215 0.4222 0.1126 0.027 Uiso 1 1 calc R U
C13 C 0.6031(2) 0.35507(9) 0.24780(16) 0.0179(4) Uani 1 1 d . .
H13 H 0.4963 0.3544 0.2372 0.021 Uiso 1 1 calc R U
C14 C 0.48022(19) 0.29970(9) 0.46097(15) 0.0143(3) Uani 1 1 d . .
C15 C 0.4616(2) 0.37218(9) 0.47016(15) 0.0168(3) Uani 1 1 d . .
H15 H 0.5357 0.4026 0.4482 0.020 Uiso 1 1 calc R U
C16 C 0.3357(2) 0.39870(9) 0.51110(16) 0.0190(4) Uani 1 1 d . .
H16 H 0.3241 0.4473 0.5177 0.023 Uiso 1 1 calc R U
C17 C 0.2262(2) 0.35448(10) 0.54253(16) 0.0193(4) Uani 1 1 d . .
H17 H 0.1394 0.3731 0.5695 0.023 Uiso 1 1 calc R U
C18 C 0.2430(2) 0.28294(10) 0.53477(16) 0.0183(4) Uani 1 1 d . .
H18 H 0.1682 0.2530 0.5572 0.022 Uiso 1 1 calc R U
C19 C 0.36821(19) 0.25565(9) 0.49455(15) 0.0155(3) Uani 1 1 d . .
H19 H 0.3792 0.2069 0.4894 0.019 Uiso 1 1 calc R U
Cl2 Cl 0.39726(5) 0.19739(2) 0.17812(4) 0.01824(9) Uani 1 1 d . .
Cl3 Cl 0.08891(5) 0.01676(2) 0.22649(4) 0.01875(9) Uani 1 1 d . .
Cl4 Cl 0.08831(5) 0.17904(2) 0.28053(4) 0.01949(10) Uani 1 1 d . .
Cl5 Cl 0.39791(6) 0.03586(3) 0.11923(6) 0.03748(14) Uani 1 1 d . .
Mo1 Mo 0.27877(2) 0.10116(2) 0.25069(2) 0.01400(5) Uani 1 1 d . .
O1 O 0.37364(16) 0.08593(7) 0.38472(13) 0.0251(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'
Mo Mo -1.6832 0.6857 '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
C14 C1 C2 121.35(15)
C14 C1 C8 119.31(15)
C2 C1 C8 119.34(15)
C3 C2 C7 118.92(16)
C3 C2 C1 119.57(16)
C7 C2 C1 121.51(15)
C4 C3 C2 120.53(16)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.70(17)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 C6 120.48(17)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 120.25(17)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 C2 120.06(16)
C6 C7 H7 120.0
C2 C7 H7 120.0
C13 C8 C9 119.30(16)
C13 C8 C1 120.81(16)
C9 C8 C1 119.86(16)
C10 C9 C8 119.96(17)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 120.26(17)
C9 C10 H10 119.9
C11 C10 H10 119.9
C10 C11 C12 120.18(17)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 120.31(18)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C8 119.87(17)
C12 C13 H13 120.1
C8 C13 H13 120.1
C19 C14 C15 118.64(16)
C19 C14 C1 121.37(15)
C15 C14 C1 119.98(16)
C16 C15 C14 120.16(17)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 120.27(17)
C15 C16 H16 119.9
C17 C16 H16 119.9
C16 C17 C18 120.41(16)
C16 C17 H17 119.8
C18 C17 H17 119.8
C19 C18 C17 120.03(17)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C14 120.49(16)
C18 C19 H19 119.8
C14 C19 H19 119.8
O1 Mo1 Cl5 105.51(6)
O1 Mo1 Cl4 105.66(5)
Cl5 Mo1 Cl4 148.82(2)
O1 Mo1 Cl3 104.49(5)
Cl5 Mo1 Cl3 86.80(2)
Cl4 Mo1 Cl3 85.93(2)
O1 Mo1 Cl2 105.27(5)
Cl5 Mo1 Cl2 85.97(2)
Cl4 Mo1 Cl2 85.47(2)
Cl3 Mo1 Cl2 150.226(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C14 1.442(2)
C1 C2 1.444(2)
C1 C8 1.455(2)
C2 C3 1.409(2)
C2 C7 1.413(2)
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.391(3)
C4 H4 0.9500
C5 C6 1.396(3)
C5 H5 0.9500
C6 C7 1.378(2)
C6 H6 0.9500
C7 H7 0.9500
C8 C13 1.406(2)
C8 C9 1.412(2)
C9 C10 1.384(3)
C9 H9 0.9500
C10 C11 1.390(3)
C10 H10 0.9500
C11 C12 1.393(3)
C11 H11 0.9500
C12 C13 1.386(3)
C12 H12 0.9500
C13 H13 0.9500
C14 C19 1.414(2)
C14 C15 1.417(2)
C15 C16 1.384(3)
C15 H15 0.9500
C16 C17 1.390(3)
C16 H16 0.9500
C17 C18 1.396(3)
C17 H17 0.9500
C18 C19 1.381(2)
C18 H18 0.9500
C19 H19 0.9500
Cl2 Mo1 2.3527(5)
Cl3 Mo1 2.3484(5)
Cl4 Mo1 2.3427(5)
Cl5 Mo1 2.3320(6)
Mo1 O1 1.6549(14)
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
C14 C1 C2 C3 147.44(17)
C8 C1 C2 C3 -32.7(2)
C14 C1 C2 C7 -31.4(2)
C8 C1 C2 C7 148.43(17)
C7 C2 C3 C4 2.4(3)
C1 C2 C3 C4 -176.46(16)
C2 C3 C4 C5 -1.7(3)
C3 C4 C5 C6 -0.4(3)
C4 C5 C6 C7 1.8(3)
C5 C6 C7 C2 -1.0(3)
C3 C2 C7 C6 -1.0(3)
C1 C2 C7 C6 177.83(16)
C14 C1 C8 C13 -39.7(2)
C2 C1 C8 C13 140.45(17)
C14 C1 C8 C9 138.32(17)
C2 C1 C8 C9 -41.5(2)
C13 C8 C9 C10 2.7(3)
C1 C8 C9 C10 -175.34(16)
C8 C9 C10 C11 -3.1(3)
C9 C10 C11 C12 0.6(3)
C10 C11 C12 C13 2.4(3)
C11 C12 C13 C8 -2.7(3)
C9 C8 C13 C12 0.2(3)
C1 C8 C13 C12 178.22(17)
C2 C1 C14 C19 -26.8(2)
C8 C1 C14 C19 153.39(16)
C2 C1 C14 C15 154.08(16)
C8 C1 C14 C15 -25.8(2)
C19 C14 C15 C16 -0.1(3)
C1 C14 C15 C16 179.07(16)
C14 C15 C16 C17 -0.5(3)
C15 C16 C17 C18 0.9(3)
C16 C17 C18 C19 -0.6(3)
C17 C18 C19 C14 0.0(3)
C15 C14 C19 C18 0.4(3)
C1 C14 C19 C18 -178.79(16)
