# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IB008_Sarpong
_database_code_depnum_ccdc_archive 'CCDC 2234155'
loop_
_audit_author_name
_audit_author_address
'Nicholas Settineri'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2023-01-03 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_IB008_Sarpong       
;
PROBLEM: D-H Bond Without Acceptor  O2A      --H2A      .     Please Check 
RESPONSE: ... Hydroxyl hydrogens found in the 
difference map were not stable in the refinement,
thus HFIX 147 was used to place these hydrogens.
Their position in space may not be completely
accurate, resulting in H2A not having an
acceptor due to an incorrect position.
;
# end Validation Reply Form

_audit_creation_date             2022-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H18 O2'
_chemical_formula_sum            'C11 H18 O2'
_chemical_formula_weight         182.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C O H'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           102
_space_group_name_H-M_alt        'P 42 n m'
_space_group_name_Hall           'P 4n -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-y, -x, z'
'y, x, z'

_cell_length_a                   23.5301(3)
_cell_length_b                   23.5301(3)
_cell_length_c                   5.98071(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3311.31(10)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    17157
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      74.4970
_cell_measurement_theta_min      3.7280
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            32348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.282
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  14.00   0.50    3.00    --    0.00 -53.00 -71.00  176
  2  ω    -14.00  74.00   0.50    3.00    --    0.00  53.00  73.00  176
  3  ω    -63.00 -26.00   0.50   13.00    -- -100.00  53.00  73.00   74
  4  ω   -174.00 -86.00   0.50   13.00    -- -100.00 -53.00 -71.00  176
  5  ω     26.00  57.00   0.50   13.00    --  100.18 -53.00 -71.00   62
  6  ω     86.00 174.00   0.50   13.00    --  100.18  53.00  73.00  176
  7  ω    -23.00  45.00   0.50    3.00    --    0.00  77.00 120.00  136
  8  ω    -23.00  45.00   0.50    3.00    --    0.00  77.00   0.00  136
  9  ω    -23.00  45.00   0.50    3.00    --    0.00  77.00-150.00  136
 10  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00  30.00   60
 11  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00 150.00   60
 12  ω    -74.00 -29.00   0.50   13.00    -- -100.00  61.00  90.00   90
 13  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00   0.00   60
 14  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00  60.00   60
 15  ω   -178.00 -86.00   0.50   13.00    -- -100.00 -30.00-120.00  184
 16  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00 120.00   60
 17  ω   -178.00 -88.00   0.50   13.00    -- -100.00 -15.00 -30.00  180
 18  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00-150.00   60
 19  ω    -74.00 -29.00   0.50   13.00    -- -100.00  61.00   0.00   90
 20  ω    -54.00 -24.00   0.50   13.00    -- -100.00  45.00-120.00   60
 21  ω     88.00 175.00   0.50   13.00    --  100.18  15.00 150.00  174
 22  ω     29.00  68.00   0.50   13.00    --  100.18 -61.00-150.00   78
 23  ω     29.00  68.00   0.50   13.00    --  100.18 -61.00 -90.00   78
 24  ω     29.00  68.00   0.50   13.00    --  100.18 -61.00 150.00   78
 25  ω     29.00  68.00   0.50   13.00    --  100.18 -61.00-180.00   78
 26  ω     87.00 175.00   0.50   13.00    --  100.18  30.00-180.00  176
 27  ω    -13.00  22.00   0.50    3.00    --    0.00  38.00 -60.00   70
 28  ω    -13.00  80.00   0.50    3.00    --    0.00  19.00-150.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0512103000
_diffrn_orient_matrix_UB_12      0.0407996000
_diffrn_orient_matrix_UB_13      0.0026490000
_diffrn_orient_matrix_UB_21      0.0113871000
_diffrn_orient_matrix_UB_22      0.0152355000
_diffrn_orient_matrix_UB_23      -0.2465029000
_diffrn_orient_matrix_UB_31      -0.0391817000
_diffrn_orient_matrix_UB_32      -0.0488828000
_diffrn_orient_matrix_UB_33      -0.0746586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3164
_reflns_number_total             3522
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1046P)²+0.7782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1723
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(4)
 0.0(4)
2. 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, All O(H) groups
3. Restrained distances
 C7B-C8B
 1.5 with sigma of 0.01
4. Rigid body (RIGU) restrains
 C1B, C2B, C3B, C9B, C10B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1B(0.5) H1B(0.5) O2B(0.5) H2B(0.5) C1B(0.5) C2B(0.5) H2BA(0.5)
 C3B(0.5) H3B(0.5) C4B(0.5) C5B(0.5) H5BA(0.5) H5BB(0.5) H5BC(0.5) C6B(0.5)
 H6BA(0.5) H6BB(0.5) H6BC(0.5) C7B(0.5) H7B(0.5) C8B(0.5) H8BA(0.5) H8BB(0.5)
 C9B(0.5) H9B(0.5) C10B(0.5) H10B(0.5) C11B(0.5) H11D(0.5) H11E(0.5) H11F(0.5)
6.a Ternary CH refined with riding coordinates:
 C2A(H2AA), C3A(H3A), C7A(H7A), C9A(H9A), C10A(H10A), C2B(H2BA), C3B(H3B),
 C7B(H7B), C9B(H9B), C10B(H10B)
6.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C8B(H8BA,H8BB)
6.c Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC), C11A(H11A,H11B,H11C), C5B(H5BA,H5BB,
 H5BC), C6B(H6BA,H6BB,H6BC), C11B(H11D,H11E,H11F)
6.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O2A(H2A), O1B(H1B), O2B(H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1A O 0.37755(10) 0.14647(10) 0.3552(4) 0.0476(6) Uani 1 1 d . . . . .
H1A H 0.3486 0.1510 0.2750 0.071 Uiso 1 1 calc R U . . .
O2A O 0.58272(10) 0.14931(9) 0.2226(4) 0.0465(6) Uani 1 1 d . . . . .
H2A H 0.5885 0.1154 0.2606 0.070 Uiso 1 1 calc R U . . .
C1A C 0.48223(13) 0.13808(13) 0.3437(6) 0.0418(7) Uani 1 1 d . . . . .
C2A C 0.42772(13) 0.15542(13) 0.2229(6) 0.0413(7) Uani 1 1 d . . . . .
H2AA H 0.4243 0.1313 0.0859 0.050 Uiso 1 1 calc R U . . .
C3A C 0.43876(15) 0.21675(14) 0.1467(6) 0.0484(8) Uani 1 1 d . . . . .
H3A H 0.4202 0.2284 0.0035 0.058 Uiso 1 1 calc R U . . .
C4A C 0.43979(17) 0.26255(16) 0.3356(8) 0.0588(9) Uani 1 1 d . . . . .
C5A C 0.4460(2) 0.32151(17) 0.2286(11) 0.0825(15) Uani 1 1 d . . . . .
H5AA H 0.4777 0.3210 0.1220 0.124 Uiso 1 1 calc R U . . .
H5AB H 0.4536 0.3497 0.3453 0.124 Uiso 1 1 calc R U . . .
H5AC H 0.4108 0.3314 0.1502 0.124 Uiso 1 1 calc R U . . .
C6A C 0.39447(19) 0.26567(19) 0.5163(8) 0.0697(12) Uani 1 1 d . . . . .
H6AA H 0.3585 0.2781 0.4501 0.105 Uiso 1 1 calc R U . . .
H6AB H 0.4062 0.2929 0.6314 0.105 Uiso 1 1 calc R U . . .
H6AC H 0.3895 0.2281 0.5840 0.105 Uiso 1 1 calc R U . . .
C7A C 0.49942(18) 0.23846(16) 0.3949(8) 0.0596(10) Uani 1 1 d . . . . .
H7A H 0.5283 0.2666 0.4477 0.072 Uiso 1 1 calc R U . . .
C8A C 0.49615(15) 0.18235(16) 0.5240(6) 0.0519(8) Uani 1 1 d . . . . .
H8AA H 0.4659 0.1838 0.6390 0.062 Uiso 1 1 calc R U . . .
H8AB H 0.5328 0.1737 0.5974 0.062 Uiso 1 1 calc R U . . .
C9A C 0.50560(16) 0.21736(14) 0.1476(8) 0.0514(8) Uani 1 1 d . . . . .
H9A H 0.5254 0.2428 0.0386 0.062 Uiso 1 1 calc R U . . .
C10A C 0.52427(13) 0.15619(13) 0.1596(6) 0.0418(7) Uani 1 1 d . . . . .
H10A H 0.5160 0.1360 0.0162 0.050 Uiso 1 1 calc R U . . .
C11A C 0.48575(15) 0.07710(15) 0.4204(7) 0.0480(8) Uani 1 1 d . . . . .
H11A H 0.4611 0.0717 0.5508 0.072 Uiso 1 1 calc R U . . .
H11B H 0.5251 0.0681 0.4610 0.072 Uiso 1 1 calc R U . . .
H11C H 0.4734 0.0519 0.2993 0.072 Uiso 1 1 calc R U . . .
O1B O 0.7883(3) 0.3492(3) 0.5333(12) 0.0456(15) Uani 0.5 1 d . . P A -1
H1B H 0.7992 0.3762 0.4520 0.068 Uiso 0.5 1 calc R U P A -1
O2B O 0.6600(3) 0.1886(3) 0.4887(13) 0.0497(16) Uani 0.5 1 d . . P A -1
H2B H 0.6315 0.1802 0.4111 0.075 Uiso 0.5 1 calc R U P A -1
C1B C 0.7358(15) 0.2596(14) 0.5294(10) 0.043(3) Uani 0.5 1 d . U P A -1
C2B C 0.7435(6) 0.3198(9) 0.425(4) 0.043(3) Uani 0.5 1 d . U P A -1
H2BA H 0.7523 0.3160 0.2623 0.052 Uiso 0.5 1 calc R U P A -1
C3B C 0.6841(4) 0.3463(4) 0.4538(16) 0.051(2) Uani 0.5 1 d . U P A -1
H3B H 0.6718 0.3738 0.3358 0.061 Uiso 0.5 1 calc R U P A -1
C4B C 0.6671(4) 0.3609(3) 0.6975(16) 0.0599(19) Uani 0.5 1 d . . P A -1
C5B C 0.7037(4) 0.3945(3) 0.8479(16) 0.0607(19) Uani 0.5 1 d . . P A -1
H5BA H 0.7410 0.3762 0.8602 0.091 Uiso 0.5 1 calc R U P A -1
H5BB H 0.6861 0.3967 0.9961 0.091 Uiso 0.5 1 calc R U P A -1
H5BC H 0.7083 0.4329 0.7872 0.091 Uiso 0.5 1 calc R U P A -1
C6B C 0.605(2) 0.389(2) 0.695(2) 0.088(7) Uani 0.5 1 d . . P A -1
H6BA H 0.6054 0.4239 0.6065 0.132 Uiso 0.5 1 calc R U P A -1
H6BB H 0.5931 0.3977 0.8487 0.132 Uiso 0.5 1 calc R U P A -1
H6BC H 0.5776 0.3621 0.6292 0.132 Uiso 0.5 1 calc R U P A -1
C7B C 0.6598(3) 0.2961(3) 0.7383(15) 0.0554(17) Uani 0.5 1 d D . P A -1
H7B H 0.6328 0.2815 0.8537 0.066 Uiso 0.5 1 calc R U P A -1
C8B C 0.7326(3) 0.2878(3) 0.7689(12) 0.0455(16) Uani 0.5 1 d D . P A -1
H8BA H 0.7535 0.3242 0.7803 0.055 Uiso 0.5 1 calc R U P A -1
H8BB H 0.7433 0.2618 0.8919 0.055 Uiso 0.5 1 calc R U P A -1
C9B C 0.6465(4) 0.2902(4) 0.4810(19) 0.057(2) Uani 0.5 1 d . U P A -1
H9B H 0.6060 0.2909 0.4303 0.068 Uiso 0.5 1 calc R U P A -1
C10B C 0.6838(10) 0.2416(6) 0.411(4) 0.049(3) Uani 0.5 1 d . U P A -1
H10B H 0.6897 0.2412 0.2449 0.059 Uiso 0.5 1 calc R U P A -1
C11B C 0.7823(8) 0.2166(6) 0.4996(11) 0.0596(18) Uani 0.5 1 d . . P A -1
H11D H 0.7952 0.2169 0.3438 0.089 Uiso 0.5 1 calc R U P A -1
H11E H 0.7679 0.1787 0.5375 0.089 Uiso 0.5 1 calc R U P A -1
H11F H 0.8142 0.2261 0.5982 0.089 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1A H1A 0.8400 . ?
O1A C2A 1.437(4) . ?
O2A H2A 0.8400 . ?
O2A C10A 1.435(4) . ?
C1A C2A 1.528(4) . ?
C1A C8A 1.534(5) . ?
C1A C10A 1.540(5) . ?
C1A C11A 1.509(4) . ?
C2A H2AA 1.0000 . ?
C2A C3A 1.535(5) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.561(5) . ?
C3A C9A 1.573(5) . ?
C4A C5A 1.535(6) . ?
C4A C6A 1.520(6) . ?
C4A C7A 1.554(5) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A H7A 1.0000 . ?
C7A C8A 1.532(6) . ?
C7A C9A 1.567(6) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A H9A 1.0000 . ?
C9A C10A 1.507(4) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
O1B H1B 0.8400 . ?
O1B C2B 1.42(2) . ?
O2B H2B 0.8400 . ?
O2B C10B 1.45(2) . ?
C1B C2B 1.56(4) . ?
C1B C8B 1.581(15) . ?
C1B C10B 1.48(4) . ?
C1B C11B 1.501(9) . ?
C2B H2BA 1.0000 . ?
C2B C3B 1.540(15) . ?
C3B H3B 1.0000 . ?
C3B C4B 1.550(13) . ?
C3B C9B 1.598(16) . ?
C4B C5B 1.474(12) . ?
C4B C6B 1.61(3) . ?
C4B C7B 1.553(10) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C7B H7B 1.0000 . ?
C7B C8B 1.732(8) . ?
C7B C9B 1.577(14) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B H9B 1.0000 . ?
C9B C10B 1.503(18) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?

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
C2A O1A H1A 109.5 . . ?
C10A O2A H2A 109.5 . . ?
C2A C1A C8A 109.3(3) . . ?
C2A C1A C10A 97.3(3) . . ?
C8A C1A C10A 100.2(3) . . ?
C11A C1A C2A 116.4(3) . . ?
C11A C1A C8A 114.8(3) . . ?
C11A C1A C10A 116.4(3) . . ?
O1A C2A C1A 113.0(3) . . ?
O1A C2A H2AA 107.6 . . ?
O1A C2A C3A 116.1(3) . . ?
C1A C2A H2AA 107.6 . . ?
C1A C2A C3A 104.4(3) . . ?
C3A C2A H2AA 107.6 . . ?
C2A C3A H3A 116.0 . . ?
C2A C3A C4A 115.9(3) . . ?
C2A C3A C9A 100.2(2) . . ?
C4A C3A H3A 116.0 . . ?
C4A C3A C9A 88.6(3) . . ?
C9A C3A H3A 116.0 . . ?
C5A C4A C3A 108.9(4) . . ?
C5A C4A C7A 109.8(4) . . ?
C6A C4A C3A 122.5(3) . . ?
C6A C4A C5A 108.7(4) . . ?
C6A C4A C7A 119.3(4) . . ?
C7A C4A C3A 85.8(3) . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C4A C7A H7A 116.4 . . ?
C4A C7A C9A 89.1(3) . . ?
C8A C7A C4A 112.6(3) . . ?
C8A C7A H7A 116.4 . . ?
C8A C7A C9A 102.0(3) . . ?
C9A C7A H7A 116.4 . . ?
C1A C8A H8AA 111.0 . . ?
C1A C8A H8AB 111.0 . . ?
C7A C8A C1A 104.0(3) . . ?
C7A C8A H8AA 111.0 . . ?
C7A C8A H8AB 111.0 . . ?
H8AA C8A H8AB 109.0 . . ?
C3A C9A H9A 117.9 . . ?
C7A C9A C3A 85.0(3) . . ?
C7A C9A H9A 117.9 . . ?
C10A C9A C3A 106.4(3) . . ?
C10A C9A C7A 106.5(3) . . ?
C10A C9A H9A 117.9 . . ?
O2A C10A C1A 113.4(3) . . ?
O2A C10A C9A 113.6(3) . . ?
O2A C10A H10A 110.9 . . ?
C1A C10A H10A 110.9 . . ?
C9A C10A C1A 96.4(3) . . ?
C9A C10A H10A 110.9 . . ?
C1A C11A H11A 109.5 . . ?
C1A C11A H11B 109.5 . . ?
C1A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C2B O1B H1B 109.5 . . ?
C10B O2B H2B 109.5 . . ?
C2B C1B C8B 89.2(19) . . ?
C10B C1B C2B 99.5(6) . . ?
C10B C1B C8B 121.1(19) . . ?
C10B C1B C11B 111(2) . . ?
C11B C1B C2B 119(3) . . ?
C11B C1B C8B 115.2(11) . . ?
O1B C2B C1B 110.3(19) . . ?
O1B C2B H2BA 109.5 . . ?
O1B C2B C3B 115.2(15) . . ?
C1B C2B H2BA 109.5 . . ?
C3B C2B C1B 102.7(13) . . ?
C3B C2B H2BA 109.5 . . ?
C2B C3B H3B 116.5 . . ?
C2B C3B C4B 115.4(11) . . ?
C2B C3B C9B 100.3(10) . . ?
C4B C3B H3B 116.5 . . ?
C4B C3B C9B 86.8(8) . . ?
C9B C3B H3B 116.5 . . ?
C3B C4B C6B 108.6(8) . . ?
C3B C4B C7B 87.7(6) . . ?
C5B C4B C3B 122.8(7) . . ?
C5B C4B C6B 108.6(18) . . ?
C5B C4B C7B 119.6(8) . . ?
C7B C4B C6B 108(2) . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
C4B C6B H6BA 109.5 . . ?
C4B C6B H6BB 109.5 . . ?
C4B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C4B C7B H7B 121.1 . . ?
C4B C7B C8B 91.1(5) . . ?
C4B C7B C9B 87.4(7) . . ?
C8B C7B H7B 121.1 . . ?
C9B C7B H7B 121.1 . . ?
C9B C7B C8B 106.9(6) . . ?
C1B C8B C7B 90.0(12) . . ?
C1B C8B H8BA 113.6 . . ?
C1B C8B H8BB 113.6 . . ?
C7B C8B H8BA 113.6 . . ?
C7B C8B H8BB 113.6 . . ?
H8BA C8B H8BB 110.9 . . ?
C3B C9B H9B 119.0 . . ?
C7B C9B C3B 85.2(7) . . ?
C7B C9B H9B 119.0 . . ?
C10B C9B C3B 106.0(11) . . ?
C10B C9B C7B 103.0(11) . . ?
C10B C9B H9B 119.0 . . ?
O2B C10B C1B 114(2) . . ?
O2B C10B C9B 109.8(16) . . ?
O2B C10B H10B 111.4 . . ?
C1B C10B C9B 97.5(11) . . ?
C1B C10B H10B 111.4 . . ?
C9B C10B H10B 111.4 . . ?
C1B C11B H11D 109.5 . . ?
C1B C11B H11E 109.5 . . ?
C1B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?

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
O1A C2A C3A C4A 53.8(4) . . . . ?
O1A C2A C3A C9A 147.3(3) . . . . ?
C1A C2A C3A C4A -71.3(3) . . . . ?
C1A C2A C3A C9A 22.1(3) . . . . ?
C2A C1A C8A C7A -56.4(3) . . . . ?
C2A C1A C10A O2A 176.1(2) . . . . ?
C2A C1A C10A C9A 57.0(3) . . . . ?
C2A C3A C4A C5A -175.1(3) . . . . ?
C2A C3A C4A C6A -46.9(5) . . . . ?
C2A C3A C4A C7A 75.4(3) . . . . ?
C2A C3A C9A C7A -91.0(3) . . . . ?
C2A C3A C9A C10A 14.8(4) . . . . ?
C3A C4A C7A C8A -77.3(4) . . . . ?
C3A C4A C7A C9A 25.3(3) . . . . ?
C3A C9A C10A O2A -164.0(3) . . . . ?
C3A C9A C10A C1A -45.0(4) . . . . ?
C4A C3A C9A C7A 25.1(3) . . . . ?
C4A C3A C9A C10A 130.9(3) . . . . ?
C4A C7A C8A C1A 77.2(4) . . . . ?
C4A C7A C9A C3A -25.2(3) . . . . ?
C4A C7A C9A C10A -130.9(3) . . . . ?
C5A C4A C7A C8A 174.1(4) . . . . ?
C5A C4A C7A C9A -83.3(4) . . . . ?
C6A C4A C7A C8A 47.9(5) . . . . ?
C6A C4A C7A C9A 150.5(4) . . . . ?
C7A C9A C10A O2A -74.4(4) . . . . ?
C7A C9A C10A C1A 44.6(3) . . . . ?
C8A C1A C2A O1A -73.9(3) . . . . ?
C8A C1A C2A C3A 53.2(3) . . . . ?
C8A C1A C10A O2A 64.9(3) . . . . ?
C8A C1A C10A C9A -54.2(3) . . . . ?
C8A C7A C9A C3A 87.7(3) . . . . ?
C8A C7A C9A C10A -18.0(4) . . . . ?
C9A C3A C4A C5A 84.3(4) . . . . ?
C9A C3A C4A C6A -147.5(4) . . . . ?
C9A C3A C4A C7A -25.2(3) . . . . ?
C9A C7A C8A C1A -16.8(4) . . . . ?
C10A C1A C2A O1A -177.5(2) . . . . ?
C10A C1A C2A C3A -50.4(3) . . . . ?
C10A C1A C8A C7A 45.1(3) . . . . ?
C11A C1A C2A O1A 58.2(4) . . . . ?
C11A C1A C2A C3A -174.7(3) . . . . ?
C11A C1A C8A C7A 170.7(3) . . . . ?
C11A C1A C10A O2A -59.6(4) . . . . ?
C11A C1A C10A C9A -178.7(3) . . . . ?
O1B C2B C3B C4B -49.8(16) . . . . ?
O1B C2B C3B C9B -141.1(13) . . . . ?
C1B C2B C3B C4B 70.2(16) . . . . ?
C1B C2B C3B C9B -21.2(16) . . . . ?
C2B C1B C8B C7B 88.2(13) . . . . ?
C2B C1B C10B O2B -172.8(18) . . . . ?
C2B C1B C10B C9B -56.9(11) . . . . ?
C2B C3B C4B C5B 51.1(13) . . . . ?
C2B C3B C4B C6B 179(3) . . . . ?
C2B C3B C4B C7B -73.1(10) . . . . ?
C2B C3B C9B C7B 88.8(11) . . . . ?
C2B C3B C9B C10B -13.4(19) . . . . ?
C3B C4B C7B C8B 79.6(6) . . . . ?
C3B C4B C7B C9B -27.2(6) . . . . ?
C3B C9B C10B O2B 163.6(13) . . . . ?
C3B C9B C10B C1B 44.2(18) . . . . ?
C4B C3B C9B C7B -26.5(6) . . . . ?
C4B C3B C9B C10B -128.6(12) . . . . ?
C4B C7B C8B C1B -105.3(14) . . . . ?
C4B C7B C9B C3B 26.4(6) . . . . ?
C4B C7B C9B C10B 131.8(10) . . . . ?
C5B C4B C7B C8B -47.2(9) . . . . ?
C5B C4B C7B C9B -154.1(8) . . . . ?
C6B C4B C7B C8B -171.6(8) . . . . ?
C6B C4B C7B C9B 81.5(9) . . . . ?
C7B C9B C10B O2B 74.9(15) . . . . ?
C7B C9B C10B C1B -44.5(17) . . . . ?
C8B C1B C2B O1B 51.9(17) . . . . ?
C8B C1B C2B C3B -71.3(17) . . . . ?
C8B C1B C10B O2B -78(2) . . . . ?
C8B C1B C10B C9B 38(2) . . . . ?
C8B C7B C9B C3B -63.9(7) . . . . ?
C8B C7B C9B C10B 41.4(11) . . . . ?
C9B C3B C4B C5B 151.0(8) . . . . ?
C9B C3B C4B C6B -81(2) . . . . ?
C9B C3B C4B C7B 26.8(6) . . . . ?
C9B C7B C8B C1B -17.7(15) . . . . ?
C10B C1B C2B O1B 173.4(17) . . . . ?
C10B C1B C2B C3B 50.1(8) . . . . ?
C10B C1B C8B C7B -12(2) . . . . ?
C11B C1B C2B O1B -67(2) . . . . ?
C11B C1B C2B C3B 170.1(18) . . . . ?
C11B C1B C8B C7B -150(3) . . . . ?
C11B C1B C10B O2B 61(2) . . . . ?
C11B C1B C10B C9B 177.3(17) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.242 254.4 35.8 ?
2 0.500 0.500 -0.876 254.4 35.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.931
_oxdiff_exptl_absorpt_empirical_full_min 0.592
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(4)
2 0.0(4)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IB007_Sarpong
_database_code_depnum_ccdc_archive 'CCDC 2234156'
loop_
_audit_author_name
_audit_author_address
'Nicholas Settineri'
;University of California, Berkeley
United States of America
;
_audit_update_record             
;
2023-01-03 deposited with the CCDC.	2023-03-08 downloaded from the CCDC.
;
_audit_creation_date             2022-12-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 Br O2'
_chemical_formula_sum            'C11 H13 Br O2'
_chemical_formula_weight         257.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O H'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   6.69110(10)
_cell_length_b                   19.8327(3)
_cell_length_c                   8.71150(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.3160(10)
_cell_angle_gamma                90
_cell_volume                     1140.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11563
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.3250
_cell_measurement_theta_min      5.5910
_shelx_estimated_absorpt_T_max   0.677
_shelx_estimated_absorpt_T_min   0.411
_exptl_absorpt_coefficient_mu    4.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12788
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.440
_diffrn_reflns_theta_min         4.459
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00-180.00   64
  2  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00 -90.00   64
  3  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00 -30.00   64
  4  ω    -28.00  24.00   0.50    0.50    --   50.71 -19.00-120.00  104
  5  ω    -28.00  24.00   0.50    0.50    --   50.71 -19.00  90.00  104
  6  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00 150.00   64
  7  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00  90.00   64
  8  ω     36.00  68.00   0.50    0.50    --  107.75 -61.00  60.00   64
  9  ω     35.00 109.00   0.50    0.50    --  107.75-111.00  60.00  148
 10  ω     35.00 109.00   0.50    0.50    --  107.75-111.00-120.00  148
 11  ω     35.00 109.00   0.50    0.50    --  107.75-111.00-180.00  148
 12  ω     32.00 135.00   0.50    0.50    --  107.75 -88.00  59.00  206
 13  ω     35.00 109.00   0.50    0.50    --  107.75-111.00  90.00  148
 14  ω    -25.00  78.00   0.50    0.50    --   50.71 -88.00  59.00  206
 15  ω     31.00 106.00   0.50    0.50    --  107.75 -94.00 150.00  150
 16  ω     96.00 148.00   0.50    0.50    --  107.75  15.00 120.00  104
 17  ω     81.00 124.00   0.50    0.50    --   50.71  77.00 150.00   86
 18  ω     97.00 128.00   0.50    0.50    --  107.75  61.00 120.00   62
 19  ω    136.00 173.00   0.50    0.50    --  107.75  61.00 120.00   74
 20  ω     94.00 175.00   0.50    0.50    --  107.75  45.00 150.00  162
 21  ω    115.00 141.00   0.50    0.50    --  107.75  30.00 150.00   52
 22  ω    102.00 138.00   0.50    0.50    --  107.75  15.00 -30.00   72
 23  ω    146.00 174.00   0.50    0.50    --  107.75  15.00 -30.00   56
 24  ω     85.00 175.00   0.50    0.50    --  107.75  77.00-150.00  180
 25  ω     94.00 175.00   0.50    0.50    --  107.75  45.00-120.00  162
 26  ω     81.00 124.00   0.50    0.50    --   50.71  77.00-150.00   86
 27  ω     76.00 124.00   0.50    0.50    --   50.71 125.00 -90.00   96
 28  ω     76.00 124.00   0.50    0.50    --   50.71 125.00 -60.00   96
 29  ω     83.00 175.00   0.50    0.50    --  107.75 111.00  60.00  184
 30  ω    119.00 175.00   0.50    0.50    --  107.75  88.00 176.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2085216000
_diffrn_orient_matrix_UB_12      -0.0322319000
_diffrn_orient_matrix_UB_13      -0.0562698000
_diffrn_orient_matrix_UB_21      -0.0624403000
_diffrn_orient_matrix_UB_22      0.0620718000
_diffrn_orient_matrix_UB_23      -0.1028479000
_diffrn_orient_matrix_UB_31      0.0837087000
_diffrn_orient_matrix_UB_32      -0.0339318000
_diffrn_orient_matrix_UB_33      -0.1355061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2305
_reflns_number_total             2325
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+1.1062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_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.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.74623(3) 0.60666(2) 0.88997(2) 0.02024(11) Uani 1 1 d . . . . .
O1 O 0.3697(2) 0.72387(7) 0.38708(17) 0.0208(3) Uani 1 1 d . . . . .
O2 O 1.0182(2) 0.66247(7) 0.64372(16) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.6793(3) 0.65057(9) 0.6997(2) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.4940(3) 0.66602(10) 0.6257(2) 0.0166(4) Uani 1 1 d . . . . .
H2 H 0.3706 0.6546 0.6599 0.020 Uiso 1 1 calc R U . . .
C3 C 0.5115(3) 0.70390(9) 0.4815(2) 0.0156(4) Uani 1 1 d . . . . .
C4 C 0.7350(3) 0.71487(9) 0.4722(2) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.8398(3) 0.67448(9) 0.6112(2) 0.0139(4) Uani 1 1 d . . . . .
C6 C 0.7894(3) 0.78998(10) 0.4963(2) 0.0189(4) Uani 1 1 d . . . . .
H6A H 0.7549 0.8051 0.5959 0.028 Uiso 1 1 calc R U . . .
H6B H 0.7130 0.8165 0.4116 0.028 Uiso 1 1 calc R U . . .
H6C H 0.9348 0.7961 0.4969 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7935(3) 0.68830(10) 0.3191(2) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.7269 0.7166 0.2319 0.021 Uiso 1 1 calc R U . . .
H7B H 0.9417 0.6929 0.3240 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7348(3) 0.61578(10) 0.2864(2) 0.0192(4) Uani 1 1 d . . . . .
H8 H 0.5937 0.6063 0.2694 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8572(3) 0.56314(11) 0.2783(2) 0.0219(4) Uani 1 1 d . . . . .
C10 C 1.0839(4) 0.56694(12) 0.3006(3) 0.0314(5) Uani 1 1 d . . . . .
H10A H 1.1303 0.5569 0.2020 0.047 Uiso 1 1 calc R U . . .
H10B H 1.1416 0.5341 0.3795 0.047 Uiso 1 1 calc R U . . .
H10C H 1.1278 0.6124 0.3350 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7703(4) 0.49390(12) 0.2387(3) 0.0335(5) Uani 1 1 d . . . . .
H11A H 0.6222 0.4959 0.2263 0.050 Uiso 1 1 calc R U . . .
H11B H 0.8215 0.4624 0.3226 0.050 Uiso 1 1 calc R U . . .
H11C H 0.8108 0.4784 0.1414 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.8620(19) . ?
O1 C3 1.217(2) . ?
O2 C5 1.205(2) . ?
C1 C2 1.337(3) . ?
C1 C5 1.497(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.484(3) . ?
C3 C4 1.526(3) . ?
C4 C5 1.525(3) . ?
C4 C6 1.540(3) . ?
C4 C7 1.542(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.506(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.336(3) . ?
C9 C10 1.499(3) . ?
C9 C11 1.509(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 Br1 127.37(15) . . ?
C2 C1 C5 111.46(17) . . ?
C5 C1 Br1 121.16(14) . . ?
C1 C2 H2 125.4 . . ?
C1 C2 C3 109.26(17) . . ?
C3 C2 H2 125.4 . . ?
O1 C3 C2 125.24(18) . . ?
O1 C3 C4 125.52(17) . . ?
C2 C3 C4 109.23(16) . . ?
C3 C4 C6 110.04(16) . . ?
C3 C4 C7 112.66(16) . . ?
C5 C4 C3 102.20(15) . . ?
C5 C4 C6 109.35(15) . . ?
C5 C4 C7 111.03(16) . . ?
C6 C4 C7 111.19(16) . . ?
O2 C5 C1 125.62(17) . . ?
O2 C5 C4 126.95(17) . . ?
C1 C5 C4 107.42(15) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 108.9 . . ?
C4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C4 113.27(16) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8 116.1 . . ?
C9 C8 C7 127.8(2) . . ?
C9 C8 H8 116.1 . . ?
C8 C9 C10 124.8(2) . . ?
C8 C9 C11 120.4(2) . . ?
C10 C9 C11 114.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
Br1 C1 C2 C3 177.19(14) . . . . ?
Br1 C1 C5 O2 7.7(3) . . . . ?
Br1 C1 C5 C4 -173.57(13) . . . . ?
O1 C3 C4 C5 -175.42(18) . . . . ?
O1 C3 C4 C6 68.5(2) . . . . ?
O1 C3 C4 C7 -56.2(3) . . . . ?
C1 C2 C3 O1 178.35(19) . . . . ?
C1 C2 C3 C4 -2.7(2) . . . . ?
C2 C1 C5 O2 -173.30(19) . . . . ?
C2 C1 C5 C4 5.4(2) . . . . ?
C2 C3 C4 C5 5.61(19) . . . . ?
C2 C3 C4 C6 -110.47(18) . . . . ?
C2 C3 C4 C7 124.83(17) . . . . ?
C3 C4 C5 O2 172.25(19) . . . . ?
C3 C4 C5 C1 -6.42(19) . . . . ?
C3 C4 C7 C8 -53.3(2) . . . . ?
C4 C7 C8 C9 -115.6(2) . . . . ?
C5 C1 C2 C3 -1.7(2) . . . . ?
C5 C4 C7 C8 60.6(2) . . . . ?
C6 C4 C5 O2 -71.2(2) . . . . ?
C6 C4 C5 C1 110.16(17) . . . . ?
C6 C4 C7 C8 -177.40(17) . . . . ?
C7 C4 C5 O2 51.9(3) . . . . ?
C7 C4 C5 C1 -126.79(16) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C7 C8 C9 C11 -177.9(2) . . . . ?

_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 3.865
_oxdiff_exptl_absorpt_empirical_full_min 0.668
