#------------------------------------------------------------------------------
#$Date: 2021-09-06 11:32:04 +0200 (Mon 06 de Sep de 2021) $
#$Revision: 268578 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/85/7128562.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_7128562
loop_
_publ_author_name
'Fang, Lili'
'Fan, Shuaixin'
'Wu, Weiping'
'Li, Tielei'
'Zhu, Jin'
_publ_section_title
;
 Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium
 ylides and cyclopropanols for δ-diketone synthesis.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7386
_journal_page_last               7389
_journal_paper_doi               10.1039/d1cc02576g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C19 H14 Br2 N2'
_chemical_formula_sum            'C19 H14 Br2 N2'
_chemical_formula_weight         430.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc282cd4
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.660(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.235(3)
_cell_length_b                   5.7050(11)
_cell_length_c                   18.500(4)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      2.76
_cell_volume                     1690.6(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16744
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_min         2.758
_exptl_absorpt_coefficient_mu    6.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.5428
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0241
_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)+(0.0249P)²+1.1818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2918
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02576g2.cif
_cod_data_source_block           t_a
_cod_depositor_comments          'Adding full bibliography for 7128562.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128562
_shelx_shelxl_version_number     2018/3
_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   0.408
_shelx_estimated_absorpt_t_max   0.463
loop_
_space_group_symop_operation_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_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
C1 C 0.01792(13) 0.8939(4) 0.12339(12) 0.0379(5) Uani 1 1 d . . . . .
Br1 Br -0.07366(2) 0.80614(5) 0.03155(2) 0.05582(10) Uani 1 1 d . . . . .
N1 N 0.31988(10) 0.7594(3) 0.37705(9) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.01291(14) 1.0937(5) 0.16289(14) 0.0484(6) Uani 1 1 d . . . . .
H2 H -0.035929 1.188065 0.145007 0.058 Uiso 1 1 calc R U . . .
Br2 Br 0.73264(2) -0.16716(4) 0.34776(2) 0.03845(9) Uani 1 1 d . . . . .
N2 N 0.31711(10) 0.5188(3) 0.48231(9) 0.0334(4) Uani 1 1 d . . . . .
C5 C 0.15458(14) 0.8186(4) 0.21478(13) 0.0405(5) Uani 1 1 d . . . . .
H5 H 0.203081 0.722766 0.232318 0.049 Uiso 1 1 calc R U . . .
C4 C 0.15215(12) 1.0199(3) 0.25619(11) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.08031(15) 1.1559(4) 0.22944(14) 0.0435(5) Uani 1 1 d . . . . .
H3 H 0.077124 1.293675 0.257032 0.052 Uiso 1 1 calc R U . . .
C6 C 0.08790(14) 0.7545(4) 0.14858(13) 0.0424(5) Uani 1 1 d . . . . .
H6 H 0.090460 0.616235 0.120937 0.051 Uiso 1 1 calc R U . . .
C7 C 0.22682(13) 1.0924(4) 0.32754(12) 0.0369(4) Uani 1 1 d . . . . .
H7A H 0.271933 1.148540 0.310842 0.044 Uiso 1 1 calc R U . . .
H7B H 0.210390 1.224023 0.353720 0.044 Uiso 1 1 calc R U . . .
C8 C 0.25966(12) 0.8936(3) 0.38478(11) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.22682(13) 0.8481(4) 0.44125(12) 0.0369(5) Uani 1 1 d . . . . .
H9 H 0.184256 0.943945 0.446722 0.044 Uiso 1 1 calc R U . . .
C10 C 0.25831(13) 0.6580(4) 0.48928(12) 0.0360(5) Uani 1 1 d . . . . .
H10 H 0.237176 0.625262 0.528910 0.043 Uiso 1 1 calc R U . . .
C11 C 0.34566(12) 0.5763(3) 0.42634(11) 0.0305(4) Uani 1 1 d . . . . .
C12 C 0.40991(12) 0.4198(4) 0.41909(11) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.425074 0.287675 0.452687 0.040 Uiso 1 1 calc R U . . .
C13 C 0.44864(12) 0.4471(3) 0.36958(11) 0.0310(4) Uani 1 1 d . . . . .
H13 H 0.433087 0.578785 0.335822 0.037 Uiso 1 1 calc R U . . .
C14 C 0.51348(12) 0.2920(3) 0.36224(11) 0.0296(4) Uani 1 1 d . . . . .
C15 C 0.53275(13) 0.0736(3) 0.39966(11) 0.0328(4) Uani 1 1 d . . . . .
H15 H 0.500808 0.018424 0.428467 0.039 Uiso 1 1 calc R U . . .
C16 C 0.59728(13) -0.0629(3) 0.39545(11) 0.0318(4) Uani 1 1 d . . . . .
H16 H 0.610319 -0.209493 0.421535 0.038 Uiso 1 1 calc R U . . .
C17 C 0.64251(12) 0.0191(3) 0.35228(10) 0.0294(4) Uani 1 1 d . . . . .
C18 C 0.62424(12) 0.2305(3) 0.31291(11) 0.0300(4) Uani 1 1 d . . . . .
H18 H 0.655505 0.282472 0.283085 0.036 Uiso 1 1 calc R U . . .
C19 C 0.55937(12) 0.3648(3) 0.31788(11) 0.0302(4) Uani 1 1 d . . . . .
H19 H 0.545863 0.509334 0.290574 0.036 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 C6 121.3(2) . . ?
C2 C1 Br1 119.80(17) . . ?
C6 C1 Br1 118.92(18) . . ?
C8 N1 C11 116.43(17) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C10 N2 C11 116.00(17) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C7 121.00(19) . . ?
C5 C4 C7 120.97(18) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C4 112.46(17) . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C9 121.50(19) . . ?
N1 C8 C7 117.29(18) . . ?
C9 C8 C7 121.18(19) . . ?
C10 C9 C8 117.40(19) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
N2 C10 C9 122.64(19) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N2 C11 N1 126.02(18) . . ?
N2 C11 C12 115.23(17) . . ?
N1 C11 C12 118.74(17) . . ?
C13 C12 C11 125.50(18) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C12 C13 C14 125.88(18) . . ?
C12 C13 H13 117.1 . . ?
C14 C13 H13 117.1 . . ?
C19 C14 C15 118.13(18) . . ?
C19 C14 C13 119.31(17) . . ?
C15 C14 C13 122.54(18) . . ?
C16 C15 C14 121.36(18) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 118.49(18) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 122.00(18) . . ?
C18 C17 Br2 119.52(14) . . ?
C16 C17 Br2 118.48(15) . . ?
C17 C18 C19 118.65(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C14 121.33(18) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
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
C1 C2 1.374(4) . ?
C1 C6 1.374(3) . ?
C1 Br1 1.910(2) . ?
N1 C8 1.339(3) . ?
N1 C11 1.350(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
Br2 C17 1.9092(19) . ?
N2 C10 1.331(3) . ?
N2 C11 1.341(3) . ?
C5 C6 1.384(3) . ?
C5 C4 1.390(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.388(3) . ?
C4 C7 1.522(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.384(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.467(3) . ?
C12 C13 1.327(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.471(3) . ?
C13 H13 0.9500 . ?
C14 C19 1.397(3) . ?
C14 C15 1.404(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(4) . . . . ?
Br1 C1 C2 C3 -179.65(18) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C5 C4 C7 -178.2(2) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C7 C4 C3 C2 178.1(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
Br1 C1 C6 C5 179.54(18) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C3 C4 C7 C8 131.6(2) . . . . ?
C5 C4 C7 C8 -49.9(3) . . . . ?
C11 N1 C8 C9 1.0(3) . . . . ?
C11 N1 C8 C7 -177.00(16) . . . . ?
C4 C7 C8 N1 91.2(2) . . . . ?
C4 C7 C8 C9 -86.8(2) . . . . ?
N1 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 177.67(18) . . . . ?
C11 N2 C10 C9 1.2(3) . . . . ?
C8 C9 C10 N2 -0.9(3) . . . . ?
C10 N2 C11 N1 -0.4(3) . . . . ?
C10 N2 C11 C12 -179.51(17) . . . . ?
C8 N1 C11 N2 -0.7(3) . . . . ?
C8 N1 C11 C12 178.38(17) . . . . ?
N2 C11 C12 C13 -177.78(19) . . . . ?
N1 C11 C12 C13 3.0(3) . . . . ?
C11 C12 C13 C14 179.60(18) . . . . ?
C12 C13 C14 C19 -168.36(19) . . . . ?
C12 C13 C14 C15 10.2(3) . . . . ?
C19 C14 C15 C16 2.4(3) . . . . ?
C13 C14 C15 C16 -176.20(18) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 C16 C17 Br2 179.08(14) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
Br2 C17 C18 C19 -179.03(14) . . . . ?
C17 C18 C19 C14 0.8(3) . . . . ?
C15 C14 C19 C18 -2.3(3) . . . . ?
C13 C14 C19 C18 176.29(17) . . . . ?
