#------------------------------------------------------------------------------
#$Date: 2021-10-29 01:26:01 +0300 (Fri, 29 Oct 2021) $
#$Revision: 270105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/50/1565047.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_1565047
loop_
_publ_author_name
'Kurogi, Takashi'
'Irifune, Keiichi'
'Takai, Kazuhiko'
_publ_section_title
;
 Chromium carbides and cyclopropenylidenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04910K
_journal_year                    2021
_chemical_formula_moiety         'C11 H20 Br3 Cr O2'
_chemical_formula_sum            'C11 H20 Br3 Cr O2'
_chemical_formula_weight         476.00
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-30 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.494(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.606(3)
_cell_length_b                   11.192(3)
_cell_length_c                   13.906(4)
_cell_measurement_reflns_used    5285
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.9
_cell_volume                     1611.6(8)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9683
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.936
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    8.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DME/hexane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0266
_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)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2976
_reflns_number_total             3663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04910k2.cif
_cod_data_source_block           Crcyclopropenylidene
_cod_database_code               1565047
_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_max   0.792
_shelx_estimated_absorpt_t_min   0.395
_olex2_submission_special_instructions 'No special instructions were received'
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
Cr1 Cr 0.79215(4) 0.79634(4) 0.09553(3) 0.01267(10) Uani 1 1 d . . . . .
Br1 Br 0.58371(2) 0.88220(2) 0.11121(2) 0.01779(8) Uani 1 1 d . . . . .
Br2 Br 0.75147(3) 0.61651(2) 0.18251(2) 0.01941(8) Uani 1 1 d . . . . .
Br3 Br 1.00423(2) 0.72179(2) 0.07206(2) 0.01804(8) Uani 1 1 d . . . . .
C1 C 0.6983(3) 0.7196(2) -0.0331(2) 0.0163(6) Uani 1 1 d . . . . .
C2 C 0.6725(3) 0.6221(2) -0.0954(2) 0.0181(6) Uani 1 1 d . . . . .
C3 C 0.5978(3) 0.7204(2) -0.1165(2) 0.0169(6) Uani 1 1 d . . . . .
C4 C 0.7043(3) 0.4974(2) -0.1152(2) 0.0233(7) Uani 1 1 d . . . . .
H4A H 0.798929 0.485430 -0.095832 0.028 Uiso 1 1 calc R . . . .
H4B H 0.676497 0.480594 -0.186532 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6372(4) 0.4125(3) -0.0578(3) 0.0392(9) Uani 1 1 d . . . . .
H5A H 0.661150 0.432300 0.012411 0.059 Uiso 1 1 calc GR . . . .
H5B H 0.663491 0.330328 -0.067859 0.059 Uiso 1 1 calc GR . . . .
H5C H 0.543449 0.419999 -0.080932 0.059 Uiso 1 1 calc GR . . . .
C6 C 0.4893(3) 0.7852(2) -0.1799(2) 0.0195(6) Uani 1 1 d . . . . .
H6A H 0.517509 0.815544 -0.238718 0.023 Uiso 1 1 calc R . . . .
H6B H 0.466414 0.854878 -0.143315 0.023 Uiso 1 1 calc R . . . .
C7 C 0.3697(3) 0.7075(3) -0.2132(2) 0.0243(7) Uani 1 1 d . . . . .
H7A H 0.390686 0.639932 -0.251793 0.036 Uiso 1 1 calc GR . . . .
H7B H 0.300686 0.755087 -0.253876 0.036 Uiso 1 1 calc GR . . . .
H7C H 0.340815 0.677430 -0.155360 0.036 Uiso 1 1 calc GR . . . .
O1 O 0.88606(17) 0.89313(15) 0.22122(14) 0.0163(4) Uani 1 1 d . . . . .
O2 O 0.83244(17) 0.95641(15) 0.03218(14) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.9662(3) 0.8396(3) 0.3080(2) 0.0243(7) Uani 1 1 d . . . . .
H8A H 1.045701 0.808924 0.291842 0.037 Uiso 1 1 calc GR . . . .
H8B H 0.919273 0.773727 0.330804 0.037 Uiso 1 1 calc GR . . . .
H8C H 0.988019 0.899838 0.360075 0.037 Uiso 1 1 calc GR . . . .
C9 C 0.9458(3) 0.9997(2) 0.1941(2) 0.0221(6) Uani 1 1 d . . . . .
H9A H 1.030722 0.980295 0.179268 0.026 Uiso 1 1 calc R . . . .
H9B H 0.959412 1.058132 0.248773 0.026 Uiso 1 1 calc R . . . .
C10 C 0.8579(3) 1.0507(2) 0.1051(2) 0.0207(6) Uani 1 1 d . . . . .
H10A H 0.776392 1.078178 0.121562 0.025 Uiso 1 1 calc R . . . .
H10B H 0.899418 1.119622 0.079716 0.025 Uiso 1 1 calc R . . . .
C11 C 0.7558(3) 0.9985(3) -0.0609(2) 0.0214(6) Uani 1 1 d . . . . .
H11A H 0.668453 1.017905 -0.053001 0.032 Uiso 1 1 calc GR . . . .
H11B H 0.751079 0.935962 -0.110845 0.032 Uiso 1 1 calc GR . . . .
H11C H 0.795920 1.070099 -0.081671 0.032 Uiso 1 1 calc GR . . . .
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'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
Br1 Cr1 Br3 175.95(2) . . ?
Br2 Cr1 Br1 91.13(2) . . ?
Br2 Cr1 Br3 92.89(2) . . ?
C1 Cr1 Br1 87.99(8) . . ?
C1 Cr1 Br2 89.00(8) . . ?
C1 Cr1 Br3 91.57(8) . . ?
C1 Cr1 O1 174.03(9) . . ?
C1 Cr1 O2 95.57(9) . . ?
O1 Cr1 Br1 89.90(5) . . ?
O1 Cr1 Br2 96.62(6) . . ?
O1 Cr1 Br3 90.15(5) . . ?
O2 Cr1 Br1 88.40(5) . . ?
O2 Cr1 Br2 175.39(6) . . ?
O2 Cr1 Br3 87.64(5) . . ?
O2 Cr1 O1 78.79(7) . . ?
C2 C1 Cr1 151.0(2) . . ?
C2 C1 C3 58.17(19) . . ?
C3 C1 Cr1 150.1(2) . . ?
C1 C2 C4 147.3(3) . . ?
C3 C2 C1 61.35(19) . . ?
C3 C2 C4 151.3(3) . . ?
C1 C3 C6 148.7(3) . . ?
C2 C3 C1 60.5(2) . . ?
C2 C3 C6 150.8(3) . . ?
C2 C4 C5 110.0(3) . . ?
C3 C6 C7 113.0(2) . . ?
C8 O1 Cr1 124.33(16) . . ?
C9 O1 Cr1 111.30(16) . . ?
C9 O1 C8 110.4(2) . . ?
C10 O2 Cr1 110.82(16) . . ?
C10 O2 C11 111.8(2) . . ?
C11 O2 Cr1 122.04(15) . . ?
O1 C9 C10 107.7(2) . . ?
O2 C10 C9 106.9(2) . . ?
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
Cr1 Br1 2.4631(7) . ?
Cr1 Br2 2.4343(7) . ?
Cr1 Br3 2.4858(8) . ?
Cr1 C1 2.039(3) . ?
Cr1 O1 2.1137(19) . ?
Cr1 O2 2.0811(18) . ?
C1 C2 1.383(4) . ?
C1 C3 1.395(4) . ?
C2 C3 1.351(4) . ?
C2 C4 1.476(4) . ?
C3 C6 1.479(4) . ?
C4 C5 1.514(4) . ?
C6 C7 1.525(4) . ?
O1 C8 1.447(3) . ?
O1 C9 1.439(3) . ?
O2 C10 1.448(3) . ?
O2 C11 1.450(3) . ?
C9 C10 1.492(4) . ?
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
Cr1 C1 C2 C3 169.7(4) . . . . ?
Cr1 C1 C2 C4 -6.3(8) . . . . ?
Cr1 C1 C3 C2 -169.9(4) . . . . ?
Cr1 C1 C3 C6 10.1(8) . . . . ?
Cr1 O1 C9 C10 38.2(2) . . . . ?
Cr1 O2 C10 C9 44.8(2) . . . . ?
C1 C2 C3 C6 180.0(6) . . . . ?
C1 C2 C4 C5 82.0(5) . . . . ?
C1 C3 C6 C7 -137.2(4) . . . . ?
C2 C1 C3 C6 -180.0(5) . . . . ?
C2 C3 C6 C7 42.8(6) . . . . ?
C3 C1 C2 C4 -176.0(5) . . . . ?
C3 C2 C4 C5 -90.7(6) . . . . ?
C4 C2 C3 C1 175.5(6) . . . . ?
C4 C2 C3 C6 -4.5(9) . . . . ?
O1 C9 C10 O2 -54.1(3) . . . . ?
C8 O1 C9 C10 -179.5(2) . . . . ?
C11 O2 C10 C9 -175.4(2) . . . . ?
