#------------------------------------------------------------------------------
#$Date: 2019-07-08 09:44:38 +0300 (Mon, 08 Jul 2019) $
#$Revision: 216804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/19/1551996.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_1551996
loop_
_publ_author_name
'Manuel Alcarazo'
'Christian W. Lehmann'
'Anakuthil Anoop'
'Walter Thiel'
'Alois Furstner'
_publ_section_title
;
 Coordination chemistry at carbon
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              295
_journal_page_last               301
_journal_paper_doi               10.1038/nchem.248
_journal_volume                  1
_journal_year                    2009
_chemical_compound_source        'DCM / pentane'
_chemical_formula_moiety         'C24 H25 Cl3 Ga O2 P'
_chemical_formula_sum            'C24 H25 Cl3 Ga O2 P'
_chemical_formula_weight         552.48
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0467(2)
_cell_length_b                   16.8611(4)
_cell_length_c                   16.2834(4)
_cell_measurement_reflns_used    65439
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.32
_cell_measurement_theta_min      2.91
_cell_volume                     2465.44(10)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.18
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            66933
_diffrn_reflns_theta_full        36.35
_diffrn_reflns_theta_max         36.35
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.525
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         11849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0375P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                9367
_reflns_number_total             11849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nchem.248-s6.cif
_cod_data_source_block           6211
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_geom_angle_publ_flag' value 'N' was changed to 'n' in
accordance with the built-in table derived from the CIF Core
dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21 (52 times).

data item '_geom_angle_publ_flag' value 'Y' was changed to 'y' in
accordance with the built-in table derived from the CIF Core
dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21 (46 times).

data item '_geom_bond_publ_flag' value 'N' was changed to 'n' in
accordance with the built-in table derived from the CIF Core
dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21 (25 times).

data item '_geom_bond_publ_flag' value 'Y' was changed to 'y' in
accordance with the built-in table derived from the CIF Core
dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21 (33 times).

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1551996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14265(13) 0.66065(7) 0.65391(7) 0.01407(18) Uani 1 1 d . . .
C2 C 0.06350(13) 0.68857(7) 0.71548(7) 0.01567(19) Uani 1 1 d . . .
C3 C 0.02918(16) 0.56275(8) 0.78186(8) 0.0229(2) Uani 1 1 d . . .
H3A H 0.1253 0.5411 0.8037 0.027 Uiso 1 1 calc R . .
H3B H 0.0042 0.5438 0.7256 0.027 Uiso 1 1 calc R . .
C4 C -0.08898(19) 0.53695(10) 0.83505(10) 0.0310(3) Uani 1 1 d . . .
H4A H -0.0620 0.5549 0.8908 0.047 Uiso 1 1 calc R . .
H4B H -0.0964 0.4801 0.8345 0.047 Uiso 1 1 calc R . .
H4C H -0.1832 0.5595 0.8135 0.047 Uiso 1 1 calc R . .
C5 C -0.10041(15) 0.78735(9) 0.76667(9) 0.0251(3) Uani 1 1 d . . .
H5A H -0.1083 0.8447 0.7660 0.030 Uiso 1 1 calc R . .
H5B H -0.0667 0.7711 0.8230 0.030 Uiso 1 1 calc R . .
C6 C -0.25215(17) 0.75192(10) 0.74020(10) 0.0299(3) Uani 1 1 d . . .
H6A H -0.2844 0.7663 0.6838 0.045 Uiso 1 1 calc R . .
H6B H -0.3220 0.7718 0.7751 0.045 Uiso 1 1 calc R . .
H6C H -0.2465 0.6952 0.7449 0.045 Uiso 1 1 calc R . .
C11 C -0.06790(13) 0.74403(7) 0.52772(7) 0.01481(19) Uani 1 1 d . . .
C12 C -0.12331(15) 0.81943(7) 0.54520(9) 0.0205(2) Uani 1 1 d . . .
H12 H -0.0606 0.8571 0.5728 0.025 Uiso 1 1 calc R . .
C13 C -0.27241(15) 0.83733(8) 0.52098(10) 0.0244(3) Uani 1 1 d . . .
H13 H -0.3087 0.8873 0.5320 0.029 Uiso 1 1 calc R . .
C14 C -0.36796(15) 0.78128(9) 0.48037(9) 0.0227(2) Uani 1 1 d . . .
H14 H -0.4678 0.7936 0.4652 0.027 Uiso 1 1 calc R . .
C15 C -0.31353(14) 0.70682(8) 0.46259(8) 0.0210(2) Uani 1 1 d . . .
H15 H -0.3771 0.6694 0.4353 0.025 Uiso 1 1 calc R . .
C16 C -0.16399(13) 0.68815(7) 0.48555(7) 0.0169(2) Uani 1 1 d . . .
H16 H -0.1279 0.6386 0.4729 0.020 Uiso 1 1 calc R . .
C21 C 0.18367(13) 0.65454(7) 0.48079(7) 0.01402(18) Uani 1 1 d . . .
C22 C 0.16031(14) 0.57236(7) 0.48226(7) 0.0173(2) Uani 1 1 d . . .
H22 H 0.1110 0.5500 0.5235 0.021 Uiso 1 1 calc R . .
C23 C 0.21118(16) 0.52407(8) 0.42180(8) 0.0218(2) Uani 1 1 d . . .
H23 H 0.1960 0.4696 0.4231 0.026 Uiso 1 1 calc R . .
C24 C 0.28449(16) 0.55721(8) 0.35956(8) 0.0229(2) Uani 1 1 d . . .
H24 H 0.3200 0.5248 0.3201 0.027 Uiso 1 1 calc R . .
C25 C 0.30438(15) 0.63924(8) 0.35672(8) 0.0211(2) Uani 1 1 d . . .
H25 H 0.3513 0.6615 0.3145 0.025 Uiso 1 1 calc R . .
C26 C 0.25454(14) 0.68786(7) 0.41661(7) 0.0173(2) Uani 1 1 d . . .
H26 H 0.2680 0.7425 0.4143 0.021 Uiso 1 1 calc R . .
C31 C 0.23087(13) 0.80732(7) 0.56679(7) 0.01415(18) Uani 1 1 d . . .
C32 C 0.20697(14) 0.86382(7) 0.50305(8) 0.0173(2) Uani 1 1 d . . .
H32 H 0.1371 0.8541 0.4574 0.021 Uiso 1 1 calc R . .
C33 C 0.28797(15) 0.93440(7) 0.50832(8) 0.0201(2) Uani 1 1 d . . .
H33 H 0.2728 0.9715 0.4659 0.024 Uiso 1 1 calc R . .
C34 C 0.39164(15) 0.94946(8) 0.57717(8) 0.0207(2) Uani 1 1 d . . .
H34 H 0.4439 0.9971 0.5811 0.025 Uiso 1 1 calc R . .
C35 C 0.41693(14) 0.89337(8) 0.63995(8) 0.0198(2) Uani 1 1 d . . .
H35 H 0.4871 0.9033 0.6854 0.024 Uiso 1 1 calc R . .
C36 C 0.33737(14) 0.82207(7) 0.63499(7) 0.0171(2) Uani 1 1 d . . .
H36 H 0.3551 0.7845 0.6769 0.020 Uiso 1 1 calc R . .
O1 O 0.03455(11) 0.64955(6) 0.78308(5) 0.02012(17) Uani 1 1 d . . .
O2 O 0.01085(10) 0.76263(5) 0.71221(6) 0.01897(17) Uani 1 1 d . . .
P1 P 0.12383(3) 0.716260(17) 0.561683(18) 0.01220(5) Uani 1 1 d . . .
Cl1 Cl 0.28986(4) 0.463011(17) 0.67422(2) 0.02279(6) Uani 1 1 d . . .
Cl2 Cl 0.41200(4) 0.61995(2) 0.811945(19) 0.02276(6) Uani 1 1 d . . .
Cl3 Cl 0.49985(3) 0.623815(19) 0.60786(2) 0.02076(6) Uani 1 1 d . . .
Ga1 Ga 0.321589(15) 0.592949(8) 0.681864(8) 0.01425(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'
P P 0.1023 0.0942 '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'
Ga Ga 0.2307 1.6083 '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
_geom_angle_publ_flag
C2 C1 P1 115.59(9) . . y
C2 C1 Ga1 120.54(8) . . y
P1 C1 Ga1 119.52(6) . . y
O2 C2 O1 112.89(10) . . y
O2 C2 C1 120.19(11) . . y
O1 C2 C1 126.90(11) . . y
O1 C3 C4 107.64(12) . . y
O1 C3 H3A 110.2 . . n
C4 C3 H3A 110.2 . . n
O1 C3 H3B 110.2 . . n
C4 C3 H3B 110.2 . . n
H3A C3 H3B 108.5 . . n
C3 C4 H4A 109.5 . . n
C3 C4 H4B 109.5 . . n
H4A C4 H4B 109.5 . . n
C3 C4 H4C 109.5 . . n
H4A C4 H4C 109.5 . . n
H4B C4 H4C 109.5 . . n
O2 C5 C6 112.22(11) . . y
O2 C5 H5A 109.2 . . n
C6 C5 H5A 109.2 . . n
O2 C5 H5B 109.2 . . n
C6 C5 H5B 109.2 . . n
H5A C5 H5B 107.9 . . n
C5 C6 H6A 109.5 . . n
C5 C6 H6B 109.5 . . n
H6A C6 H6B 109.5 . . n
C5 C6 H6C 109.5 . . n
H6A C6 H6C 109.5 . . n
H6B C6 H6C 109.5 . . n
C16 C11 C12 119.37(11) . . y
C16 C11 P1 119.19(9) . . y
C12 C11 P1 121.41(9) . . y
C13 C12 C11 119.67(12) . . y
C13 C12 H12 120.2 . . n
C11 C12 H12 120.2 . . n
C12 C13 C14 120.79(12) . . y
C12 C13 H13 119.6 . . n
C14 C13 H13 119.6 . . n
C15 C14 C13 119.74(12) . . y
C15 C14 H14 120.1 . . n
C13 C14 H14 120.1 . . n
C14 C15 C16 120.26(12) . . y
C14 C15 H15 119.9 . . n
C16 C15 H15 119.9 . . n
C15 C16 C11 120.16(12) . . y
C15 C16 H16 119.9 . . n
C11 C16 H16 119.9 . . n
C22 C21 C26 119.35(11) . . y
C22 C21 P1 119.74(9) . . y
C26 C21 P1 120.90(9) . . y
C23 C22 C21 120.02(11) . . y
C23 C22 H22 120.0 . . n
C21 C22 H22 120.0 . . n
C24 C23 C22 120.34(12) . . y
C24 C23 H23 119.8 . . n
C22 C23 H23 119.8 . . n
C23 C24 C25 119.73(12) . . y
C23 C24 H24 120.1 . . n
C25 C24 H24 120.1 . . n
C26 C25 C24 120.45(12) . . y
C26 C25 H25 119.8 . . n
C24 C25 H25 119.8 . . n
C25 C26 C21 120.07(11) . . y
C25 C26 H26 120.0 . . n
C21 C26 H26 120.0 . . n
C36 C31 C32 119.61(11) . . y
C36 C31 P1 119.93(9) . . y
C32 C31 P1 120.46(9) . . y
C33 C32 C31 120.01(11) . . y
C33 C32 H32 120.0 . . n
C31 C32 H32 120.0 . . n
C32 C33 C34 120.11(12) . . y
C32 C33 H33 119.9 . . n
C34 C33 H33 119.9 . . n
C35 C34 C33 120.09(11) . . y
C35 C34 H34 120.0 . . n
C33 C34 H34 120.0 . . n
C34 C35 C36 120.29(12) . . y
C34 C35 H35 119.9 . . n
C36 C35 H35 119.9 . . n
C35 C36 C31 119.86(11) . . y
C35 C36 H36 120.1 . . n
C31 C36 H36 120.1 . . n
C2 O1 C3 119.39(10) . . y
C2 O2 C5 120.32(11) . . y
C1 P1 C31 114.60(5) . . y
C1 P1 C21 107.91(5) . . y
C31 P1 C21 108.35(5) . . y
C1 P1 C11 112.75(5) . . y
C31 P1 C11 106.30(5) . . y
C21 P1 C11 106.57(5) . . y
C1 Ga1 Cl3 111.79(3) . . y
C1 Ga1 Cl1 117.36(4) . . y
Cl3 Ga1 Cl1 107.684(14) . . y
C1 Ga1 Cl2 107.20(3) . . y
Cl3 Ga1 Cl2 105.385(14) . . y
Cl1 Ga1 Cl2 106.666(14) . . y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3834(16) . y
C1 P1 1.7610(11) . y
C1 Ga1 1.9880(11) . y
C2 O2 1.3352(15) . y
C2 O1 1.3354(14) . y
C3 O1 1.4643(17) . y
C3 C4 1.519(2) . y
C3 H3A 0.9700 . n
C3 H3B 0.9700 . n
C4 H4A 0.9600 . n
C4 H4B 0.9600 . n
C4 H4C 0.9600 . n
C5 O2 1.4799(16) . y
C5 C6 1.511(2) . y
C5 H5A 0.9700 . n
C5 H5B 0.9700 . n
C6 H6A 0.9600 . n
C6 H6B 0.9600 . n
C6 H6C 0.9600 . n
C11 C16 1.4035(17) . y
C11 C12 1.4083(17) . y
C11 P1 1.8168(12) . y
C12 C13 1.3918(19) . y
C12 H12 0.9300 . n
C13 C14 1.392(2) . y
C13 H13 0.9300 . n
C14 C15 1.392(2) . y
C14 H14 0.9300 . n
C15 C16 1.3951(18) . y
C15 H15 0.9300 . n
C16 H16 0.9300 . n
C21 C22 1.4023(16) . y
C21 C26 1.4078(16) . y
C21 P1 1.8123(11) . y
C22 C23 1.3978(17) . y
C22 H22 0.9300 . n
C23 C24 1.3937(19) . y
C23 H23 0.9300 . n
C24 C25 1.396(2) . y
C24 H24 0.9300 . n
C25 C26 1.3904(17) . y
C25 H25 0.9300 . n
C26 H26 0.9300 . n
C31 C36 1.4013(16) . y
C31 C32 1.4061(16) . y
C31 P1 1.8118(11) . y
C32 C33 1.3947(17) . y
C32 H32 0.9300 . n
C33 C34 1.3949(19) . y
C33 H33 0.9300 . n
C34 C35 1.3912(19) . y
C34 H34 0.9300 . n
C35 C36 1.3984(17) . y
C35 H35 0.9300 . n
C36 H36 0.9300 . n
Cl1 Ga1 2.2112(3) . y
Cl2 Ga1 2.2231(3) . y
Cl3 Ga1 2.1900(3) . y
