#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/31/4303114.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_4303114
loop_
_publ_author_name
'Sharonna Greenberg'
'Douglas W. Stephan'
_publ_section_title
;
Phosphines Bearing Alkyne Substituents: Synthesis and Hydrophosphination
Polymerization
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8623
_journal_page_last               8631
_journal_paper_doi               10.1021/ic9012284
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C20 H21 Br'
_chemical_formula_weight         341.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.984(3)
_cell_length_b                   10.408(2)
_cell_length_c                   13.080(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     1714.2(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0770
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12780
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    2.390
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0401
_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)+(0.0426P)²+0.3267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2200
_reflns_number_total             3009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9012284_si_002_1.cif
_cod_data_source_block           BrC6H2(iPr)R2C=CPh
_cod_original_cell_volume        1714.2(6)
_cod_database_code               4303114
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
Br1 Br 0.47903(3) 0.33635(3) 0.02220(3) 0.03397(15) Uani 1 1 d . . .
C3 C 0.3029(3) 0.0504(3) 0.1950(3) 0.0267(8) Uani 1 1 d . . .
C4 C 0.2480(3) -0.0447(3) 0.2427(3) 0.0281(8) Uani 1 1 d . . .
C5 C 0.2317(3) 0.3321(3) 0.0041(3) 0.0315(8) Uani 1 1 d . . .
H5A H 0.2767 0.4075 0.0034 0.038 Uiso 1 1 calc R . .
C6 C 0.4083(2) 0.2240(3) 0.0980(3) 0.0244(8) Uani 1 1 d . . .
C7 C 0.2468(3) 0.1452(3) 0.1296(3) 0.0282(8) Uani 1 1 d . . .
H7A H 0.1734 0.1492 0.1191 0.034 Uiso 1 1 calc R . .
C8 C 0.2975(2) 0.2340(3) 0.0796(3) 0.0261(8) Uani 1 1 d . . .
C9 C 0.0871(3) -0.3167(3) 0.2507(3) 0.0353(9) Uani 1 1 d . . .
H9A H 0.0717 -0.3020 0.1784 0.042 Uiso 1 1 calc R . .
C10 C 0.4680(2) 0.1340(3) 0.1669(3) 0.0262(8) Uani 1 1 d . . .
C11 C 0.4134(3) 0.0471(3) 0.2144(3) 0.0278(8) Uani 1 1 d . . .
H11A H 0.4511 -0.0145 0.2601 0.033 Uiso 1 1 calc R . .
C12 C 0.1747(3) -0.2547(3) 0.4267(3) 0.0365(9) Uani 1 1 d . . .
H12A H 0.2186 -0.1990 0.4735 0.044 Uiso 1 1 calc R . .
C13 C 0.5890(3) 0.1254(3) 0.1906(3) 0.0300(8) Uani 1 1 d . . .
H13A H 0.6144 0.2020 0.1607 0.036 Uiso 1 1 calc R . .
C14 C 0.2038(3) -0.1277(3) 0.2779(3) 0.0284(8) Uani 1 1 d . . .
C15 C 0.2034(3) 0.2766(3) -0.1070(3) 0.0433(10) Uani 1 1 d . . .
H15A H 0.2669 0.2490 -0.1257 0.065 Uiso 1 1 calc R . .
H15B H 0.1686 0.3411 -0.1558 0.065 Uiso 1 1 calc R . .
H15C H 0.1566 0.2045 -0.1096 0.065 Uiso 1 1 calc R . .
C16 C 0.1539(2) -0.2327(3) 0.3196(3) 0.0261(8) Uani 1 1 d . . .
C17 C 0.0436(3) -0.4218(3) 0.2897(3) 0.0409(10) Uani 1 1 d . . .
H17A H -0.0001 -0.4783 0.2435 0.049 Uiso 1 1 calc R . .
C18 C 0.1297(3) -0.3604(3) 0.4645(3) 0.0440(10) Uani 1 1 d . . .
H18A H 0.1439 -0.3753 0.5367 0.053 Uiso 1 1 calc R . .
C19 C 0.0647(3) -0.4428(3) 0.3960(4) 0.0415(10) Uani 1 1 d . . .
H19A H 0.0348 -0.5132 0.4219 0.050 Uiso 1 1 calc R . .
C20 C 0.1330(3) 0.3771(3) 0.0384(4) 0.0483(11) Uani 1 1 d . . .
H20A H 0.1540 0.4124 0.1082 0.072 Uiso 1 1 calc R . .
H20B H 0.0863 0.3055 0.0380 0.072 Uiso 1 1 calc R . .
H20C H 0.0969 0.4418 -0.0095 0.072 Uiso 1 1 calc R . .
C22 C 0.6240(3) 0.0093(4) 0.1382(4) 0.0750(17) Uani 1 1 d . . .
H22A H 0.5912 0.0113 0.0640 0.113 Uiso 1 1 calc R . .
H22B H 0.6032 -0.0676 0.1684 0.113 Uiso 1 1 calc R . .
H22C H 0.6998 0.0106 0.1489 0.113 Uiso 1 1 calc R . .
C34 C 0.6379(3) 0.1265(4) 0.3088(3) 0.0580(12) Uani 1 1 d . . .
H34A H 0.6151 0.2021 0.3392 0.087 Uiso 1 1 calc R . .
H34B H 0.7139 0.1268 0.3216 0.087 Uiso 1 1 calc R . .
H34C H 0.6156 0.0515 0.3402 0.087 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'
Br Br -0.2901 2.4595 '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
C7 C3 C11 119.4(3) . . ?
C7 C3 C4 120.8(3) . . ?
C11 C3 C4 119.8(3) . . ?
C14 C4 C3 176.3(4) . . ?
C15 C5 C8 109.3(3) . . ?
C15 C5 C20 111.8(3) . . ?
C8 C5 C20 113.0(3) . . ?
C10 C6 C8 123.0(3) . . ?
C10 C6 Br1 119.0(2) . . ?
C8 C6 Br1 118.0(2) . . ?
C8 C7 C3 121.7(3) . . ?
C7 C8 C6 117.0(3) . . ?
C7 C8 C5 119.7(3) . . ?
C6 C8 C5 123.2(3) . . ?
C17 C9 C16 120.1(4) . . ?
C11 C10 C6 117.5(3) . . ?
C11 C10 C13 119.0(3) . . ?
C6 C10 C13 123.5(3) . . ?
C10 C11 C3 121.2(3) . . ?
C16 C12 C18 119.8(3) . . ?
C22 C13 C34 111.7(3) . . ?
C22 C13 C10 111.3(3) . . ?
C34 C13 C10 111.1(3) . . ?
C4 C14 C16 177.2(3) . . ?
C12 C16 C9 119.2(3) . . ?
C12 C16 C14 120.9(3) . . ?
C9 C16 C14 119.8(3) . . ?
C19 C17 C9 120.2(4) . . ?
C19 C18 C12 120.5(4) . . ?
C17 C19 C18 120.1(3) . . ?
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
Br1 C6 1.907(3) . ?
C3 C7 1.389(4) . ?
C3 C11 1.395(4) . ?
C3 C4 1.447(4) . ?
C4 C14 1.191(4) . ?
C5 C15 1.523(5) . ?
C5 C8 1.528(4) . ?
C5 C20 1.531(5) . ?
C6 C10 1.397(4) . ?
C6 C8 1.403(4) . ?
C7 C8 1.388(4) . ?
C9 C17 1.385(5) . ?
C9 C16 1.395(5) . ?
C10 C11 1.386(4) . ?
C10 C13 1.528(4) . ?
C12 C16 1.380(5) . ?
C12 C18 1.392(5) . ?
C13 C22 1.513(5) . ?
C13 C34 1.521(5) . ?
C14 C16 1.443(4) . ?
C17 C19 1.367(5) . ?
C18 C19 1.372(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660733
2 PubChem 139127050
