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#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/20/7052093.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_7052093
loop_
_publ_author_name
'Green, Shaun P.'
'Jones, Cameron'
'Stasch, Andreas'
'Rose, Richard P.'
_publ_section_title
;
 ?GaI?: A new reagent for chemo- and diastereoselective C?C bond
 forming reactions
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              127
_journal_paper_doi               10.1039/b613669a
_journal_volume                  31
_journal_year                    2007
_chemical_formula_sum            'C21 H18 O'
_chemical_formula_weight         286.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.69(3)
_cell_angle_beta                 100.00(3)
_cell_angle_gamma                106.81(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7983(12)
_cell_length_b                   9.0444(18)
_cell_length_c                   15.820(3)
_cell_measurement_temperature    150(2)
_cell_volume                     774.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4993
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.2482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                1927
_reflns_number_total             2689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b613669a.txt
_cod_data_source_block           compound10
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052093
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3415(3) 0.37865(19) 0.15478(11) 0.0502(5) Uani 1 1 d . . .
C1 C 0.1863(4) 0.4442(3) 0.16040(15) 0.0371(5) Uani 1 1 d . . .
C2 C -0.0036(4) 0.3930(2) 0.21647(14) 0.0354(5) Uani 1 1 d . . .
H2 H -0.1641 0.3969 0.1829 0.043 Uiso 1 1 calc R . .
C3 C 0.1838(4) 0.5819(2) 0.11334(14) 0.0330(5) Uani 1 1 d . . .
C4 C 0.3515(4) 0.6234(3) 0.05964(14) 0.0378(6) Uani 1 1 d . . .
H4 H 0.4641 0.5664 0.0549 0.045 Uiso 1 1 calc R . .
C5 C 0.3562(4) 0.7474(3) 0.01281(15) 0.0435(6) Uani 1 1 d . . .
H5 H 0.4688 0.7734 -0.0247 0.052 Uiso 1 1 calc R . .
C6 C 0.1974(4) 0.8321(3) 0.02104(15) 0.0455(6) Uani 1 1 d . . .
H6 H 0.2002 0.9168 -0.0110 0.055 Uiso 1 1 calc R . .
C7 C 0.0332(4) 0.7947(3) 0.07571(16) 0.0458(6) Uani 1 1 d . . .
H7 H -0.0734 0.8553 0.0822 0.055 Uiso 1 1 calc R . .
C8 C 0.0242(4) 0.6693(3) 0.12079(14) 0.0383(6) Uani 1 1 d . . .
H8 H -0.0916 0.6425 0.1571 0.046 Uiso 1 1 calc R . .
C9 C -0.0447(4) 0.2267(2) 0.23702(14) 0.0345(5) Uani 1 1 d . . .
C10 C 0.1444(4) 0.1800(3) 0.28198(16) 0.0446(6) Uani 1 1 d . . .
H10 H 0.3058 0.2518 0.2989 0.053 Uiso 1 1 calc R . .
C11 C 0.0993(5) 0.0298(3) 0.30224(17) 0.0466(6) Uani 1 1 d . . .
H11 H 0.2303 -0.0012 0.3324 0.056 Uiso 1 1 calc R . .
C12 C -0.1348(5) -0.0754(3) 0.27891(16) 0.0448(6) Uani 1 1 d . . .
H12 H -0.1653 -0.1782 0.2935 0.054 Uiso 1 1 calc R . .
C13 C -0.3237(5) -0.0307(3) 0.23451(15) 0.0432(6) Uani 1 1 d . . .
H13 H -0.4852 -0.1026 0.2185 0.052 Uiso 1 1 calc R . .
C14 C -0.2780(4) 0.1195(3) 0.21317(14) 0.0374(6) Uani 1 1 d . . .
H14 H -0.4088 0.1492 0.1817 0.045 Uiso 1 1 calc R . .
C15 C 0.0615(4) 0.5092(2) 0.29938(14) 0.0334(5) Uani 1 1 d . . .
C16 C 0.2946(4) 0.6119(3) 0.33199(16) 0.0416(6) Uani 1 1 d . . .
H16 H 0.4231 0.6126 0.3019 0.050 Uiso 1 1 calc R . .
C17 C 0.3443(4) 0.7139(3) 0.40773(17) 0.0461(6) Uani 1 1 d . . .
H17 H 0.5059 0.7840 0.4283 0.055 Uiso 1 1 calc R . .
C18 C 0.1635(5) 0.7159(3) 0.45424(15) 0.0419(6) Uani 1 1 d . . .
C19 C -0.0686(5) 0.6113(3) 0.42204(17) 0.0460(6) Uani 1 1 d . . .
H19 H -0.1957 0.6086 0.4531 0.055 Uiso 1 1 calc R . .
C20 C -0.1201(4) 0.5107(3) 0.34597(16) 0.0409(6) Uani 1 1 d . . .
H20 H -0.2823 0.4414 0.3252 0.049 Uiso 1 1 calc R . .
C21 C 0.2155(6) 0.8284(3) 0.53469(18) 0.0635(8) Uani 1 1 d . . .
H21A H 0.1668 0.9199 0.5204 0.095 Uiso 1 1 calc R . .
H21B H 0.3919 0.8609 0.5604 0.095 Uiso 1 1 calc R . .
H21C H 0.1219 0.7782 0.5761 0.095 Uiso 1 1 calc R . .
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'
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
O1 C1 C3 120.1(2) . . ?
O1 C1 C2 121.7(2) . . ?
C3 C1 C2 118.25(18) . . ?
C9 C2 C1 114.32(18) . . ?
C9 C2 C15 111.14(18) . . ?
C1 C2 C15 110.36(18) . . ?
C4 C3 C8 118.7(2) . . ?
C4 C3 C1 117.62(19) . . ?
C8 C3 C1 123.7(2) . . ?
C5 C4 C3 120.7(2) . . ?
C6 C5 C4 119.7(2) . . ?
C5 C6 C7 120.3(2) . . ?
C8 C7 C6 120.1(2) . . ?
C7 C8 C3 120.4(2) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C2 119.6(2) . . ?
C10 C9 C2 121.9(2) . . ?
C11 C10 C9 120.5(2) . . ?
C12 C11 C10 120.4(2) . . ?
C13 C12 C11 119.7(2) . . ?
C12 C13 C14 119.9(2) . . ?
C9 C14 C13 121.0(2) . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 C2 123.47(19) . . ?
C20 C15 C2 118.94(19) . . ?
C15 C16 C17 121.2(2) . . ?
C16 C17 C18 121.4(2) . . ?
C19 C18 C17 117.2(2) . . ?
C19 C18 C21 121.4(2) . . ?
C17 C18 C21 121.4(2) . . ?
C20 C19 C18 121.7(2) . . ?
C19 C20 C15 121.0(2) . . ?
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
O1 C1 1.224(3) . ?
C1 C3 1.505(3) . ?
C1 C2 1.525(3) . ?
C2 C9 1.524(3) . ?
C2 C15 1.530(3) . ?
C3 C4 1.392(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.382(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.375(3) . ?
C13 C14 1.389(3) . ?
C15 C16 1.382(3) . ?
C15 C20 1.389(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.385(3) . ?
C18 C19 1.383(3) . ?
C18 C21 1.491(3) . ?
C19 C20 1.380(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13077081
2 PubChem 139175763
