#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:31:08 +0200 (lun 05 de jul de 2021) $
#$Revision: 267150 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/73/7707381.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_7707381
loop_
_publ_author_name
'Paparo, Albert'
'Matthews, Aidan J. R.'
'Smith, Cory D.'
'Edwards, Alison J.'
'Yuvaraj, K.'
'Jones, Cameron'
_publ_section_title
;
 N-Heterocyclic carbene, carbodiphosphorane and diphosphine adducts of
 beryllium dihalides: synthesis, characterisation and reduction studies.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7604
_journal_page_last               7609
_journal_paper_doi               10.1039/d1dt01393a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_sum            'C54 H74 Be2 Br2 N4'
_chemical_formula_weight         957.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-04-26 deposited with the CCDC.	2021-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.21(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.360(3)
_cell_length_b                   14.990(3)
_cell_length_c                   14.390(3)
_cell_measurement_reflns_used    41884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.498
_cell_measurement_theta_min      2.935
_cell_volume                     2572.7(10)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'Blu-Ice (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CifTAB
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7109
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            41884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.248
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'Australian Synchrotron'
_exptl_absorpt_coefficient_mu    1.613
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   XDS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.121
_refine_diff_density_min         -1.216
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4781
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0439
_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)+(0.0362P)²+3.0044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4452
_reflns_number_total             4781
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01393a2.cif
_cod_data_source_block           Cj1481
_cod_depositor_comments
'Adding full bibliography for 7707372--7707383.cif.'
_cod_original_cell_volume        2572.8(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7707381
_shelx_shelxl_version_number     2016/6
_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   0.868
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.59162(2) 0.35685(2) 0.63068(2) 0.02088(10) Uani 1 1 d . . . . .
N1 N 0.34146(16) 0.33069(12) 0.37087(13) 0.0137(4) Uani 1 1 d . . . . .
C1 C 0.4471(2) 0.36401(14) 0.40115(16) 0.0148(5) Uani 1 1 d . . . . .
Be1 Be 0.5069(3) 0.4303(2) 0.5042(2) 0.0171(6) Uani 1 1 d D . . . .
H1 H 0.4280(19) 0.4987(14) 0.520(2) 0.029(8) Uiso 1 1 d D . . . .
N2 N 0.49531(17) 0.34158(12) 0.32925(13) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.3234(2) 0.28958(15) 0.28171(16) 0.0188(5) Uani 1 1 d . . . . .
H2 H 0.256204 0.261865 0.246077 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4196(2) 0.29670(15) 0.25581(16) 0.0193(5) Uani 1 1 d . . . . .
H3 H 0.433449 0.275042 0.197942 0.023 Uiso 1 1 calc R U . . .
C4 C 0.26391(19) 0.32453(15) 0.43102(15) 0.0157(4) Uani 1 1 d . . . . .
C5 C 0.2645(2) 0.24605(16) 0.48303(17) 0.0211(5) Uani 1 1 d . . . . .
C6 C 0.1904(2) 0.24049(18) 0.54153(19) 0.0289(6) Uani 1 1 d . . . . .
H6 H 0.189396 0.188294 0.578753 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1188(3) 0.3100(2) 0.5457(2) 0.0331(6) Uani 1 1 d . . . . .
H7 H 0.069034 0.305343 0.585770 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1190(2) 0.38658(18) 0.49173(19) 0.0268(5) Uani 1 1 d . . . . .
H8 H 0.068638 0.433646 0.495051 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1912(2) 0.39587(15) 0.43292(16) 0.0184(5) Uani 1 1 d . . . . .
C10 C 0.3386(2) 0.16708(17) 0.47636(19) 0.0256(6) Uani 1 1 d . . . . .
H10 H 0.389314 0.185389 0.435806 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4123(3) 0.13907(18) 0.5748(2) 0.0334(7) Uani 1 1 d . . . . .
H11A H 0.455504 0.190558 0.606426 0.050 Uiso 1 1 calc R U . . .
H11B H 0.463777 0.091834 0.566518 0.050 Uiso 1 1 calc R U . . .
H11C H 0.364825 0.116841 0.614671 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2680(3) 0.08827(19) 0.4263(2) 0.0360(7) Uani 1 1 d . . . . .
H12A H 0.217466 0.068836 0.464685 0.054 Uiso 1 1 calc R U . . .
H12B H 0.317517 0.038871 0.420019 0.054 Uiso 1 1 calc R U . . .
H12C H 0.223792 0.106683 0.362254 0.054 Uiso 1 1 calc R U . . .
C13 C 0.1880(2) 0.47768(15) 0.37025(17) 0.0199(5) Uani 1 1 d . . . . .
H13 H 0.265985 0.488573 0.365027 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1494(3) 0.56184(17) 0.4119(2) 0.0325(6) Uani 1 1 d . . . . .
H14A H 0.069944 0.556113 0.410366 0.049 Uiso 1 1 calc R U . . .
H14B H 0.159590 0.613610 0.373469 0.049 Uiso 1 1 calc R U . . .
H14C H 0.193796 0.569859 0.478577 0.049 Uiso 1 1 calc R U . . .
C15 C 0.1142(2) 0.46048(18) 0.26872(18) 0.0299(6) Uani 1 1 d . . . . .
H15A H 0.140733 0.407068 0.242189 0.045 Uiso 1 1 calc R U . . .
H15B H 0.117959 0.511888 0.227620 0.045 Uiso 1 1 calc R U . . .
H15C H 0.036451 0.451450 0.271226 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6132(2) 0.34810(15) 0.33351(16) 0.0162(5) Uani 1 1 d . . . . .
C17 C 0.6839(2) 0.27839(15) 0.37890(15) 0.0166(5) Uani 1 1 d . . . . .
C18 C 0.7947(2) 0.28037(16) 0.37432(17) 0.0217(5) Uani 1 1 d . . . . .
H18 H 0.844122 0.233919 0.403793 0.026 Uiso 1 1 calc R U . . .
C19 C 0.8344(2) 0.34873(17) 0.32763(19) 0.0257(6) Uani 1 1 d . . . . .
H19 H 0.909967 0.348137 0.323767 0.031 Uiso 1 1 calc R U . . .
C20 C 0.7640(2) 0.41785(17) 0.28663(18) 0.0239(5) Uani 1 1 d . . . . .
H20 H 0.792813 0.465284 0.256458 0.029 Uiso 1 1 calc R U . . .
C21 C 0.6519(2) 0.41990(16) 0.28834(16) 0.0191(5) Uani 1 1 d . . . . .
C22 C 0.6416(2) 0.20304(15) 0.43042(17) 0.0199(5) Uani 1 1 d . . . . .
H22 H 0.575260 0.225908 0.450640 0.024 Uiso 1 1 calc R U . . .
C23 C 0.7292(2) 0.17311(18) 0.52143(19) 0.0291(6) Uani 1 1 d . . . . .
H23A H 0.789415 0.140724 0.503297 0.044 Uiso 1 1 calc R U . . .
H23B H 0.693728 0.133933 0.559378 0.044 Uiso 1 1 calc R U . . .
H23C H 0.760385 0.225533 0.559877 0.044 Uiso 1 1 calc R U . . .
C24 C 0.6024(3) 0.12326(17) 0.3638(2) 0.0314(6) Uani 1 1 d . . . . .
H24A H 0.546249 0.143067 0.305895 0.047 Uiso 1 1 calc R U . . .
H24B H 0.569220 0.078288 0.397395 0.047 Uiso 1 1 calc R U . . .
H24C H 0.666563 0.097334 0.345402 0.047 Uiso 1 1 calc R U . . .
C25 C 0.5759(2) 0.49580(16) 0.24100(18) 0.0245(5) Uani 1 1 d . . . . .
H25 H 0.505738 0.493143 0.263097 0.029 Uiso 1 1 calc R U . . .
C26 C 0.5441(3) 0.4853(2) 0.1313(2) 0.0420(8) Uani 1 1 d . . . . .
H26A H 0.612237 0.484305 0.108655 0.063 Uiso 1 1 calc R U . . .
H26B H 0.496804 0.535591 0.101611 0.063 Uiso 1 1 calc R U . . .
H26C H 0.502778 0.429413 0.113444 0.063 Uiso 1 1 calc R U . . .
C27 C 0.6318(3) 0.58664(18) 0.2703(2) 0.0367(7) Uani 1 1 d . . . . .
H27A H 0.653398 0.591712 0.340632 0.055 Uiso 1 1 calc R U . . .
H27B H 0.579010 0.634418 0.242711 0.055 Uiso 1 1 calc R U . . .
H27C H 0.698702 0.591779 0.246158 0.055 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Be Be 0.0005 0.0002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.55(18) . . ?
C1 N1 C4 124.13(18) . . ?
C2 N1 C4 123.47(19) . . ?
N1 C1 N2 103.90(19) . . ?
N1 C1 Be1 128.9(2) . . ?
N2 C1 Be1 127.0(2) . . ?
C1 Be1 Br1 115.09(16) . . ?
C1 Be1 H1 111.8(11) . . ?
Br1 Be1 H1 114.9(11) . . ?
C1 N2 C3 110.9(2) . . ?
C1 N2 C16 125.92(19) . . ?
C3 N2 C16 122.38(19) . . ?
C3 C2 N1 106.4(2) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 107.3(2) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C5 C4 C9 123.1(2) . . ?
C5 C4 N1 117.5(2) . . ?
C9 C4 N1 119.32(19) . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 C10 122.9(2) . . ?
C6 C5 C10 119.6(2) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 117.0(2) . . ?
C8 C9 C13 121.5(2) . . ?
C4 C9 C13 121.5(2) . . ?
C5 C10 C11 112.3(2) . . ?
C5 C10 C12 110.6(2) . . ?
C11 C10 C12 110.6(2) . . ?
C5 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 113.4(2) . . ?
C9 C13 C15 110.4(2) . . ?
C14 C13 C15 110.2(2) . . ?
C9 C13 H13 107.5 . . ?
C14 C13 H13 107.5 . . ?
C15 C13 H13 107.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 122.6(2) . . ?
C21 C16 N2 119.6(2) . . ?
C17 C16 N2 117.7(2) . . ?
C18 C17 C16 117.5(2) . . ?
C18 C17 C22 120.6(2) . . ?
C16 C17 C22 121.8(2) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 121.8(2) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 116.9(2) . . ?
C20 C21 C25 120.7(2) . . ?
C16 C21 C25 122.4(2) . . ?
C17 C22 C24 111.6(2) . . ?
C17 C22 C23 112.3(2) . . ?
C24 C22 C23 110.1(2) . . ?
C17 C22 H22 107.5 . . ?
C24 C22 H22 107.5 . . ?
C23 C22 H22 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 C26 110.3(2) . . ?
C21 C25 C27 111.2(2) . . ?
C26 C25 C27 110.4(2) . . ?
C21 C25 H25 108.3 . . ?
C26 C25 H25 108.3 . . ?
C27 C25 H25 108.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
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 Be1 2.150(3) . ?
N1 C1 1.359(3) . ?
N1 C2 1.388(3) . ?
N1 C4 1.453(3) . ?
C1 N2 1.364(3) . ?
C1 Be1 1.776(4) . ?
Be1 H1 1.474(8) . ?
N2 C3 1.388(3) . ?
N2 C16 1.446(3) . ?
C2 C3 1.340(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 C9 1.402(3) . ?
C5 C6 1.400(4) . ?
C5 C10 1.515(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.517(3) . ?
C10 C11 1.528(4) . ?
C10 C12 1.532(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.526(3) . ?
C13 C15 1.528(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.404(3) . ?
C16 C17 1.408(3) . ?
C17 C18 1.388(4) . ?
C17 C22 1.517(3) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(4) . ?
C20 H20 0.9500 . ?
C21 C25 1.518(3) . ?
C22 C24 1.530(3) . ?
C22 C23 1.531(3) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.532(4) . ?
C25 C27 1.535(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
