#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/19/1501943.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_1501943
loop_
_publ_author_name
'Krämer, Katja'
'Leong, Paul'
'Lautens, Mark'
_publ_section_title
;
 Enantioselective palladium-catalyzed carbozincation of cyclopropenes.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              819
_journal_page_last               821
_journal_paper_doi               10.1021/ol1029904
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H20'
_chemical_formula_weight         260.36
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   17.959(2)
_cell_length_b                   17.959(2)
_cell_length_c                   7.9998(5)
_cell_measurement_reflns_used    8068
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     2234.5(4)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.1090
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8068
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.6
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.034
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1418
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0782P)²+0.6754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1929
_reflns_number_gt                782
_reflns_number_total             1418
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol1029904_si_001.cif
_cod_data_source_block           k09175
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1501943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, x, z+1/2'
'y, -x+y, 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 0.3382(4) 0.3444(4) 0.1047(8) 0.0589(16) Uani 1 1 d . B .
C2 C 0.3369(4) 0.4147(4) 0.0153(7) 0.0630(16) Uani 1 1 d . . .
C3 C 0.2853(4) 0.4519(4) 0.0356(9) 0.0735(18) Uani 1 1 d . . .
H3A H 0.2415 0.4313 0.1183 0.088 Uiso 1 1 calc R . .
C4 C 0.2998(5) 0.5192(5) -0.0674(10) 0.086(2) Uani 1 1 d . . .
H4A H 0.2658 0.5458 -0.0536 0.103 Uiso 1 1 calc R . .
C5 C 0.3609(6) 0.5487(5) -0.1878(10) 0.088(2) Uani 1 1 d . . .
H5A H 0.3679 0.5946 -0.2576 0.105 Uiso 1 1 calc R . .
C6 C 0.4131(5) 0.5141(4) -0.2118(9) 0.078(2) Uani 1 1 d . . .
H6A H 0.4561 0.5359 -0.2961 0.094 Uiso 1 1 calc R . .
C7 C 0.4014(4) 0.4454(4) -0.1085(7) 0.0655(17) Uani 1 1 d . . .
C8 C 0.4456(4) 0.3963(4) -0.1040(8) 0.0661(17) Uani 1 1 d . . .
C9 C 0.5134(4) 0.4037(5) -0.1995(8) 0.076(2) Uani 1 1 d . . .
H9A H 0.5393 0.4471 -0.2825 0.091 Uiso 1 1 calc R . .
C10 C 0.5422(5) 0.3470(6) -0.1713(10) 0.089(2) Uani 1 1 d . . .
H10A H 0.5876 0.3502 -0.2377 0.106 Uiso 1 1 calc R . .
C11 C 0.5055(5) 0.2844(5) -0.0461(9) 0.085(2) Uani 1 1 d . . .
H11A H 0.5265 0.2460 -0.0266 0.102 Uiso 1 1 calc R . .
C12 C 0.4386(4) 0.2787(5) 0.0491(8) 0.0733(19) Uani 1 1 d . . .
H12A H 0.4137 0.2357 0.1333 0.088 Uiso 1 1 calc R . .
C13 C 0.4072(4) 0.3340(4) 0.0245(8) 0.0633(17) Uani 1 1 d . . .
C14 C 0.2503(5) 0.2709(4) 0.1753(8) 0.0709(19) Uani 1 1 d . B .
H14A H 0.2011 0.2807 0.1539 0.085 Uiso 1 1 calc R . .
C15 C 0.2265(5) 0.1812(5) 0.1686(9) 0.083(2) Uani 1 1 d . . .
H15A H 0.1818 0.1490 0.2538 0.100 Uiso 1 1 calc R A 1
H15B H 0.2773 0.1759 0.1969 0.100 Uiso 1 1 calc R A 1
C16 C 0.1930(7) 0.1411(6) -0.0008(14) 0.115(3) Uani 1 1 d D B 1
H16 H 0.2386 0.1530 -0.0761 0.138 Uiso 0.63(2) 1 calc PR C 1
C17 C 0.1214(10) 0.0965(13) -0.068(3) 0.137(9) Uani 0.63(2) 1 d PD B 1
H17A H 0.0704 0.0801 -0.0055 0.164 Uiso 0.63(2) 1 calc PR C 1
H17B H 0.1177 0.0789 -0.1808 0.164 Uiso 0.63(2) 1 calc PR C 1
H16A H 0.1918 0.0888 -0.0265 0.138 Uiso 0.37(2) 1 calc PR C 2
C17A C 0.1670(19) 0.173(2) -0.109(4) 0.152(16) Uani 0.37(2) 1 d PD B 2
H17C H 0.1675 0.2249 -0.0864 0.182 Uiso 0.37(2) 1 calc PR C 2
H17D H 0.1466 0.1446 -0.2131 0.182 Uiso 0.37(2) 1 calc PR C 2
C18 C 0.3166(4) 0.3357(4) 0.2950(8) 0.0708(19) Uani 1 1 d . . .
H18A H 0.3016 0.3793 0.3359 0.085 Uiso 1 1 calc R B .
C19 C 0.3607(4) 0.3119(5) 0.4225(9) 0.080(2) Uani 1 1 d . B .
H19A H 0.4155 0.3635 0.4549 0.096 Uiso 1 1 calc R . .
H19B H 0.3743 0.2692 0.3750 0.096 Uiso 1 1 calc R . .
C20 C 0.3035(5) 0.2739(5) 0.5777(8) 0.083(2) Uani 1 1 d . . .
H20A H 0.3360 0.2648 0.6659 0.125 Uiso 1 1 calc R B .
H20B H 0.2528 0.2188 0.5485 0.125 Uiso 1 1 calc R . .
H20C H 0.2851 0.3137 0.6176 0.125 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C13 105.7(5)
C2 C1 C18 116.9(6)
C13 C1 C18 126.2(6)
C2 C1 C14 117.3(6)
C13 C1 C14 126.9(6)
C18 C1 C14 58.0(4)
C3 C2 C7 120.4(6)
C3 C2 C1 131.1(6)
C7 C2 C1 108.5(6)
C4 C3 C2 118.2(7)
C5 C4 C3 122.0(7)
C4 C5 C6 121.7(7)
C5 C6 C7 118.5(7)
C2 C7 C6 119.2(7)
C2 C7 C8 109.6(6)
C6 C7 C8 131.1(6)
C9 C8 C13 122.1(7)
C9 C8 C7 130.5(6)
C13 C8 C7 107.4(6)
C10 C9 C8 118.5(7)
C9 C10 C11 120.8(8)
C12 C11 C10 119.8(8)
C13 C12 C11 121.4(7)
C12 C13 C8 117.3(7)
C12 C13 C1 134.0(6)
C8 C13 C1 108.7(6)
C15 C14 C18 124.1(6)
C15 C14 C1 122.4(6)
C18 C14 C1 60.6(4)
C14 C15 C16 112.9(6)
C17 C16 C15 136.7(14)
C19 C18 C14 122.7(6)
C19 C18 C1 123.9(6)
C14 C18 C1 61.4(4)
C18 C19 C20 110.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.462(9)
C1 C13 1.488(9)
C1 C18 1.560(8)
C1 C14 1.571(9)
C2 C3 1.397(8)
C2 C7 1.410(8)
C3 C4 1.377(9)
C4 C5 1.354(11)
C5 C6 1.373(10)
C6 C7 1.410(9)
C7 C8 1.453(9)
C8 C9 1.386(9)
C8 C13 1.419(9)
C9 C10 1.373(9)
C10 C11 1.400(11)
C11 C12 1.382(10)
C12 C13 1.380(9)
C14 C15 1.446(9)
C14 C18 1.518(9)
C15 C16 1.511(12)
C16 C17 1.246(5)
C18 C19 1.481(9)
C19 C20 1.537(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037124
