#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/75/4517544.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_4517544
loop_
_publ_author_name
'Erken, Christina'
'Hindemith, Carsten'
'Weyhermüller, Thomas'
'Hölscher, Markus'
'Werlé, Christophe'
'Leitner, Walter'
_publ_section_title
;
 Hydroamination of Aromatic Alkynes to Imines Catalyzed by
 Pd(II)-Anthraphos Complexes.
;
_journal_issue                   15
_journal_name_full               'ACS omega'
_journal_page_first              8912
_journal_page_last               8918
_journal_paper_doi               10.1021/acsomega.0c00562
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C14 H8 Br2'
_chemical_formula_sum            'C14 H8 Br2'
_chemical_formula_weight         336.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                ECH-273
_audit_creation_date             2017-10-18
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6405(14)
_cell_length_b                   3.9355(4)
_cell_length_c                   18.191(2)
_cell_measurement_reflns_used    7499
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0528
_cell_measurement_theta_min      2.6045
_cell_volume                     1119.7(2)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         1\mS
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17687
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.205
_diffrn_reflns_theta_min         2.605
_exptl_absorpt_coefficient_mu    7.204
_exptl_absorpt_correction_T_max  0.98680
_exptl_absorpt_correction_T_min  0.96175
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.777
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.445(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0274
_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)+(0.0314P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0632
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3932
_reflns_number_total             4235
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c00562_si_002.cif
_cod_data_source_block           neu
_cod_depositor_comments
'Adding full bibliography for 4517542--4517544.cif.'
_cod_database_code               4517544
_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   0.341
_shelx_estimated_absorpt_t_max   0.757
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.56129(2) 0.31348(7) 0.97979(2) 0.01587(7) Uani 1 1 d . . . . .
Br16 Br 0.60942(2) 0.88357(8) 0.73006(2) 0.01627(7) Uani 1 1 d . . . . .
C2 C 0.44484(19) 0.4491(7) 0.9720(2) 0.0131(6) Uani 1 1 d . . . . .
C3 C 0.3916(2) 0.3715(8) 1.0292(2) 0.0180(7) Uani 1 1 d . . . . .
H3 H 0.4130 0.2552 1.0711 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3039(2) 0.4662(9) 1.0256(2) 0.0197(7) Uani 1 1 d . . . . .
H4 H 0.2669 0.4147 1.0655 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2726(2) 0.6294(8) 0.9657(2) 0.0168(7) Uani 1 1 d . . . . .
H5 H 0.2138 0.6888 0.9638 0.020 Uiso 1 1 calc R U . . .
C6 C 0.3274(2) 0.7136(8) 0.9048(2) 0.0138(6) Uani 1 1 d . . . . .
C7 C 0.2964(2) 0.8821(8) 0.8432(2) 0.0145(6) Uani 1 1 d . . . . .
H7 H 0.2376 0.9427 0.8414 0.017 Uiso 1 1 calc R U . . .
C8 C 0.3491(2) 0.9650(8) 0.78362(18) 0.0123(5) Uani 1 1 d . . . . .
C9 C 0.3173(2) 1.1342(8) 0.7201(2) 0.0167(7) Uani 1 1 d . . . . .
H9 H 0.2581 1.1874 0.7171 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3698(2) 1.2213(9) 0.6637(2) 0.0164(6) Uani 1 1 d . . . . .
H10 H 0.3471 1.3332 0.6217 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4588(2) 1.1451(8) 0.6673(2) 0.0145(6) Uani 1 1 d . . . . .
H11 H 0.4957 1.2105 0.6283 0.017 Uiso 1 1 calc R U . . .
C12 C 0.49041(18) 0.9799(7) 0.7262(3) 0.0125(5) Uani 1 1 d . . . . .
C13 C 0.4386(2) 0.8780(8) 0.78784(19) 0.0114(6) Uani 1 1 d . . . . .
C14 C 0.4696(2) 0.7070(7) 0.84934(19) 0.0122(5) Uani 1 1 d . . . . .
H14 H 0.5284 0.6465 0.8514 0.015 Uiso 1 1 calc R U . . .
C15 C 0.4163(2) 0.6229(8) 0.90780(19) 0.0132(6) 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0200
0.00 0.00 1.00 0.0200
0.00 1.00 0.00 0.0950
0.00 -1.00 0.00 0.0950
1.00 0.00 0.00 0.0200
-1.00 0.00 0.00 0.0200
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
C3 C2 C15 122.7(3) . . ?
C3 C2 Br1 117.6(3) . . ?
C15 C2 Br1 119.7(3) . . ?
C2 C3 C4 119.5(3) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 C6 120.8(3) . . ?
C7 C6 C15 119.2(3) . . ?
C7 C6 C5 121.5(3) . . ?
C15 C6 C5 119.4(3) . . ?
C6 C7 C8 122.0(3) . . ?
C7 C8 C9 122.1(3) . . ?
C7 C8 C13 118.4(3) . . ?
C9 C8 C13 119.5(3) . . ?
C10 C9 C8 121.3(3) . . ?
C9 C10 C11 120.2(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 123.2(3) . . ?
C11 C12 Br16 119.0(3) . . ?
C13 C12 Br16 117.8(3) . . ?
C14 C13 C12 124.3(3) . . ?
C14 C13 C8 119.7(3) . . ?
C12 C13 C8 116.0(3) . . ?
C15 C14 C13 121.3(3) . . ?
C14 C15 C2 123.5(3) . . ?
C14 C15 C6 119.5(3) . . ?
C2 C15 C6 117.0(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 C2 1.903(3) . ?
Br16 C12 1.901(3) . ?
C2 C3 1.367(5) . ?
C2 C15 1.426(5) . ?
C3 C4 1.423(5) . ?
C4 C5 1.356(5) . ?
C5 C6 1.438(5) . ?
C6 C7 1.391(5) . ?
C6 C15 1.436(5) . ?
C7 C8 1.400(5) . ?
C8 C9 1.423(5) . ?
C8 C13 1.444(5) . ?
C9 C10 1.359(6) . ?
C10 C11 1.426(5) . ?
C11 C12 1.347(5) . ?
C12 C13 1.440(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.392(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 630683
