#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:43:21 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277102 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/70/1567096.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_1567096
loop_
_publ_author_name
'Liu, Chunyang'
'Shangguan, Xiaoyan'
'Li, Yan'
'Zhang, Qian'
_publ_section_title
;
 Copper-catalyzed radical cascade reaction of simple cyclobutanes:
 synthesis of highly functionalized cyclobutene derivatives.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              7886
_journal_page_last               7891
_journal_paper_doi               10.1039/d2sc00765g
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         '0.67(C12 H11 Br3 O)'
_chemical_formula_sum            'C8 H7.33 Br2 O0.67'
_chemical_formula_weight         273.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-19 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.526(6)
_cell_angle_gamma                90
_cell_formula_units_Z            3
_cell_length_a                   7.6142(4)
_cell_length_b                   7.1461(4)
_cell_length_c                   12.6645(7)
_cell_measurement_reflns_used    1436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0200
_cell_measurement_theta_min      6.0370
_cell_volume                     660.63(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  82.00   1.00    1.00    --   42.03  57.00 -60.00   62
  2  ω      5.00  96.00   1.00    1.00    --   42.03-125.00-150.00   91
  3  ω     20.00  63.00   1.00    1.00    --   93.50 -61.00 -30.00   43
  4  ω     13.00  62.00   1.00    1.00    --   93.50 -95.00-150.00   49
  5  ω     21.00  57.00   1.00    1.00    --   93.50-125.00   0.00   36
  6  ω     66.00  95.00   1.00    1.00    --   93.50-125.00   0.00   29
  7  ω     80.00 121.00   1.00    1.00    --   93.50 -45.00 -30.00   41
  8  ω     27.00  53.00   1.00    1.00    --   93.50 -45.00 -30.00   26
  9  ω     81.00 116.00   1.00    1.00    --   93.50 -61.00 -30.00   35
 10  ω     91.00 166.00   1.00    1.00    --   93.50 125.00 150.00   75
 11  ω     71.00 159.00   1.00    1.00    --   93.50  30.00 150.00   88
 12  ω     42.00  88.00   1.00    1.00    --   93.50-125.00-150.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0907164000
_diffrn_orient_matrix_UB_12      0.1736198000
_diffrn_orient_matrix_UB_13      -0.0652062000
_diffrn_orient_matrix_UB_21      0.1901962000
_diffrn_orient_matrix_UB_22      0.0872258000
_diffrn_orient_matrix_UB_23      0.0138412000
_diffrn_orient_matrix_UB_31      0.0089138000
_diffrn_orient_matrix_UB_32      -0.0938398000
_diffrn_orient_matrix_UB_33      -0.1078903000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2611
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.012
_diffrn_reflns_theta_max         67.012
_diffrn_reflns_theta_min         3.640
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_refine_diff_density_max         1.249
_refine_diff_density_min         -1.334
_refine_diff_density_rms         0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1474P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.2058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1091
_reflns_number_total             1269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00765g2.cif
_cod_data_source_block           20200710-2
_cod_depositor_comments
'Adding full bibliography for 1567095--1567096.cif.'
_cod_database_code               1567096
_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.
;
_reflns_odcompleteness_completeness 98.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H11A(0.5) H11B(0.5) H11C(0.5) H12A(0.5) H12B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.472
_oxdiff_exptl_absorpt_empirical_full_min 0.461
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
Br2 Br -0.05697(11) 0.52782(12) 0.78795(6) 0.0516(4) Uani 1 1 d . . . . .
Br3 Br 0.61776(14) 0.750000 0.97413(7) 0.0508(5) Uani 1 2 d S T P . .
O1 O 0.3794(10) 0.750000 0.3783(5) 0.0468(17) Uani 1 2 d S T P . .
C1 C 0.2998(14) 0.750000 0.6900(7) 0.0374(19) Uani 1 2 d S T P . .
C2 C 0.2677(13) 0.750000 0.7972(7) 0.0363(19) Uani 1 2 d S T P . .
C3 C 0.0937(13) 0.750000 0.8315(7) 0.0377(19) Uani 1 2 d S T P . .
C4 C 0.3629(13) 0.750000 0.9026(7) 0.037(2) Uani 1 2 d S T P . .
C5 C 0.3640(14) 0.750000 0.4816(7) 0.038(2) Uani 1 2 d S T P . .
C6 C 0.5103(14) 0.750000 0.5777(7) 0.042(2) Uani 1 2 d S T P . .
H6 H 0.630492 0.750000 0.573839 0.050 Uiso 1 2 calc RS T P . .
C7 C 0.4740(13) 0.750000 0.6787(7) 0.039(2) Uani 1 2 d S T P . .
H7 H 0.572423 0.750000 0.742198 0.046 Uiso 1 2 calc RS T P . .
C8 C 0.2088(14) 0.750000 0.9538(7) 0.042(2) Uani 1 2 d S T P . .
H8A H 0.198520 0.862564 0.994409 0.051 Uiso 0.5 1 calc R . . . .
H8B H 0.198520 0.637436 0.994409 0.051 Uiso 0.5 1 calc R . . . .
C9 C 0.1507(14) 0.750000 0.5935(7) 0.045(2) Uani 1 2 d S T P . .
H9 H 0.031586 0.750000 0.599252 0.054 Uiso 1 2 calc RS T P . .
C10 C 0.1800(15) 0.750000 0.4904(7) 0.050(3) Uani 1 2 d S T P . .
H10 H 0.081020 0.750000 0.427226 0.060 Uiso 1 2 calc RS T P . .
C11 C 0.544(2) 0.750000 0.2442(9) 0.065(3) Uani 1 2 d S T P . .
H11A H 0.474781 0.642283 0.210521 0.098 Uiso 0.5 1 calc GR . . A -1
H11B H 0.663222 0.746161 0.233271 0.098 Uiso 0.5 1 calc GR . . A -1
H11C H 0.481267 0.861557 0.211305 0.098 Uiso 0.5 1 calc GR . . A -1
C12 C 0.5617(15) 0.750000 0.3671(8) 0.045(2) Uani 1 2 d S T P . .
H12A H 0.627827 0.639792 0.401785 0.054 Uiso 0.5 1 calc R . . . .
H12B H 0.627827 0.860208 0.401785 0.054 Uiso 0.5 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 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O1 C12 116.7(8) . . ?
C7 C1 C2 121.5(8) . . ?
C7 C1 C9 118.2(8) . . ?
C9 C1 C2 120.2(9) . . ?
C1 C2 C3 131.9(9) . . ?
C4 C2 C1 139.0(9) . . ?
C4 C2 C3 89.1(7) . . ?
Br2 C3 Br2 109.5(5) . 4_575 ?
Br2 C3 C4 125.2(2) 4_575 . ?
Br2 C3 C4 125.2(2) . . ?
C2 C3 Br2 114.5(3) . 4_575 ?
C2 C3 Br2 114.5(3) . . ?
C2 C3 C4 41.7(5) . . ?
C2 C3 C8 89.7(7) . . ?
C8 C3 Br2 113.8(3) . . ?
C8 C3 Br2 113.8(3) . 4_575 ?
C8 C3 C4 47.9(5) . . ?
Br3 C4 C3 178.4(5) . . ?
C2 C4 Br3 132.4(7) . . ?
C2 C4 C3 49.2(6) . . ?
C2 C4 C8 99.5(8) . . ?
C8 C4 Br3 128.1(6) . . ?
C8 C4 C3 50.3(5) . . ?
O1 C5 C6 125.4(9) . . ?
O1 C5 C10 115.5(8) . . ?
C6 C5 C10 119.1(8) . . ?
C7 C6 C5 119.1(9) . . ?
C1 C7 C6 123.3(9) . . ?
C4 C8 C3 81.8(6) . . ?
C10 C9 C1 120.7(9) . . ?
C9 C10 C5 119.6(8) . . ?
O1 C12 C11 107.0(9) . . ?
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
Br2 C3 1.944(6) . ?
Br3 C4 1.894(10) . ?
O1 C5 1.347(10) . ?
O1 C12 1.435(13) . ?
C1 C2 1.446(12) . ?
C1 C7 1.374(13) . ?
C1 C9 1.411(13) . ?
C2 C3 1.507(13) . ?
C2 C4 1.325(13) . ?
C3 C4 1.991(13) . ?
C3 C8 1.548(12) . ?
C4 C8 1.493(13) . ?
C5 C6 1.396(13) . ?
C5 C10 1.437(15) . ?
C6 C7 1.384(12) . ?
C9 C10 1.386(13) . ?
C11 C12 1.523(13) . ?
