# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_zhangchangsheng_0621_auto
_database_code_depnum_ccdc_archive 'CCDC 2164218'
loop_
_audit_author_name
_audit_author_address
'Chang-sheng Zhang'
;Lanzhou University
China
;
_audit_update_record             
;
2022-04-04 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-04
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.03.08 svn.r54f81f84 for OlexSys, GUI svn.r6487)
;
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.288
_chemical_absolute_configuration ad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   5.9107(1)
_cell_length_b                   13.8035(3)
_cell_length_c                   15.3174(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1249.72(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5345
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      77.1430
_cell_measurement_theta_min      4.3250
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             505.648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.9970
_diffrn_reflns_Laue_measured_fraction_max 0.9647
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6468
_diffrn_reflns_point_group_measured_fraction_full 0.9956
_diffrn_reflns_point_group_measured_fraction_max 0.9353
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.46
_diffrn_reflns_theta_min         4.31
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9647
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  27.00   0.50    0.05    --   47.57 -29.00  24.00  102
  2  ω    -27.00  21.00   0.50    0.05    --   47.57 -19.00 -90.00   96
  3  ω    -18.00  13.00   0.50    0.05    --   47.57 -19.00-120.00   62
  4  ω     61.00  94.00   0.50    0.05    --   47.57  29.00-174.00   66
  5  ω    118.00 172.00   0.50    0.05    --  107.75  57.00 -90.00  108
  6  ω   -112.00 -87.00   0.50    0.05    -- -100.00 -29.00  24.00   50
  7  ω    -92.00 -62.00   0.50    0.05    --  -47.57-155.00 157.00   60
  8  ω   -141.00-115.00   0.50    0.05    -- -100.00 -29.00  24.00   52
  9  ω   -173.00 -88.00   0.50    0.05    -- -100.00 -96.00-150.00  170
 10  ω    -69.00 -42.00   0.50    0.05    -- -100.00  57.00-180.00   54
 11  ω   -102.00 -62.00   0.50    0.05    -- -100.00 125.00 -90.00   80
 12  ω    -52.00 -27.00   0.50    0.05    -- -100.00 125.00 -90.00   50
 13  ω   -109.00 -28.00   0.50    0.05    -- -100.00 119.00  39.00  162
 14  ω     41.00  89.00   0.50    0.05    --  107.75 -99.00  90.00   96
 15  ω     41.00  97.00   0.50    0.05    --  107.75-125.00 -90.00  112
 16  ω     37.00  62.00   0.50    0.05    --  107.75 -57.00 -90.00   50
 17  ω     76.00 101.00   0.50    0.05    --  107.75 -77.00-150.00   50
 18  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00-180.00   50
 19  ω     68.00 102.00   0.50    0.05    --  107.75 -77.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225478000
_diffrn_orient_matrix_UB_12      0.1106232000
_diffrn_orient_matrix_UB_13      -0.0094823000
_diffrn_orient_matrix_UB_21      0.2429600000
_diffrn_orient_matrix_UB_22      -0.0050348000
_diffrn_orient_matrix_UB_23      0.0362096000
_diffrn_orient_matrix_UB_31      0.0921175000
_diffrn_orient_matrix_UB_32      -0.0132365000
_diffrn_orient_matrix_UB_33      -0.0933578000
_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         0.893
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                2400
_reflns_number_total             2485
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.6592
_refine_diff_density_min         -0.2498
_refine_diff_density_rms         0.0521
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.24(10)
_refine_ls_d_res_high            0.7898
_refine_ls_d_res_low             10.2541
_refine_ls_goodness_of_fit_ref   1.0551
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.0551
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.5666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1242
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.3674(3) 0.61592(10) 0.44479(9) 0.0319(4) Uani 1.000000 .
O2 O 0.2393(3) 0.76530(11) 0.46257(12) 0.0429(4) Uani 1.000000 .
C1 C 0.4251(3) 0.44185(13) 0.45416(12) 0.0239(4) Uani 1.000000 .
C2 C 0.2328(4) 0.41966(15) 0.40471(13) 0.0286(4) Uani 1.000000 .
H2 H 0.1142(4) 0.46569(15) 0.39909(13) 0.0344(5) Uiso 1.000000 R
C3 C 0.2160(4) 0.33026(15) 0.36397(14) 0.0333(5) Uani 1.000000 .
H3 H 0.0864(4) 0.31554(15) 0.32977(14) 0.0399(6) Uiso 1.000000 R
C4 C 0.3862(4) 0.26245(16) 0.37273(14) 0.0354(5) Uani 1.000000 .
H4 H 0.3733(4) 0.20127(16) 0.34475(14) 0.0425(6) Uiso 1.000000 R
C5 C 0.5759(4) 0.28368(16) 0.42238(15) 0.0354(5) Uani 1.000000 .
H5 H 0.6925(4) 0.23691(16) 0.42898(15) 0.0425(6) Uiso 1.000000 R
C6 C 0.5947(4) 0.37348(15) 0.46239(13) 0.0303(4) Uani 1.000000 .
H6 H 0.7256(4) 0.38816(15) 0.49584(13) 0.0364(5) Uiso 1.000000 R
C7 C 0.4488(3) 0.53787(13) 0.49950(12) 0.0245(4) Uani 1.000000 .
H7 H 0.6128(3) 0.54919(13) 0.51190(12) 0.0294(5) Uiso 1.000000 R
C8 C 0.3157(3) 0.54763(14) 0.58622(12) 0.0237(4) Uani 1.000000 .
H8 H 0.1676(3) 0.51324(14) 0.58007(12) 0.0284(5) Uiso 1.000000 R
C9 C 0.2719(4) 0.65627(14) 0.58993(13) 0.0295(4) Uani 1.000000 .
H9a H 0.1202(4) 0.67009(14) 0.61429(13) 0.0354(5) Uiso 1.000000 R
H9b H 0.3874(4) 0.68934(14) 0.62604(13) 0.0354(5) Uiso 1.000000 R
C10 C 0.2873(4) 0.68830(15) 0.49534(16) 0.0336(5) Uani 1.000000 .
C11 C 0.4436(3) 0.50418(14) 0.66191(12) 0.0239(4) Uani 1.000000 .
C12 C 0.3627(4) 0.42177(14) 0.70368(12) 0.0283(4) Uani 1.000000 .
H12 H 0.2221(4) 0.39476(14) 0.68603(12) 0.0340(5) Uiso 1.000000 R
C13 C 0.4836(5) 0.37822(17) 0.77071(13) 0.0369(5) Uani 1.000000 .
H13 H 0.4256(5) 0.32197(17) 0.79859(13) 0.0443(6) Uiso 1.000000 R
C14 C 0.6891(4) 0.41695(18) 0.79690(14) 0.0410(6) Uani 1.000000 .
H14 H 0.7732(4) 0.38699(18) 0.84233(14) 0.0492(7) Uiso 1.000000 R
C15 C 0.7711(4) 0.49961(19) 0.75646(14) 0.0378(5) Uani 1.000000 .
H15 H 0.9110(4) 0.52675(19) 0.77481(14) 0.0454(6) Uiso 1.000000 R
C16 C 0.6502(4) 0.54299(16) 0.68930(13) 0.0306(4) Uani 1.000000 .
H16 H 0.7083(4) 0.59943(16) 0.66177(13) 0.0367(5) Uiso 1.000000 R


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
O1 C7 1.447(2) . ?
O1 C10 1.350(3) . ?
O2 C10 1.209(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.382(3) . ?
C1 C7 1.503(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.550(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.523(3) . ?
C8 C11 1.508(3) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 C10 1.518(3) . ?
C11 C12 1.390(3) . ?
C11 C16 1.398(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?

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
C10 O1 C7 109.60(15) . . ?
C6 C1 C2 119.25(18) . . ?
C7 C1 C2 121.24(17) . . ?
C7 C1 C6 119.50(17) . . ?
H2 C2 C1 120.12(11) . . ?
C3 C2 C1 119.76(19) . . ?
C3 C2 H2 120.12(13) . . ?
H3 C3 C2 119.75(13) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.75(12) . . ?
H4 C4 C3 120.02(12) . . ?
C5 C4 C3 119.96(19) . . ?
C5 C4 H4 120.02(13) . . ?
H5 C5 C4 120.12(13) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.12(13) . . ?
C5 C6 C1 120.8(2) . . ?
H6 C6 C1 119.62(12) . . ?
H6 C6 C5 119.62(13) . . ?
C1 C7 O1 110.97(15) . . ?
H7 C7 O1 108.41(10) . . ?
H7 C7 C1 108.41(11) . . ?
C8 C7 O1 105.25(15) . . ?
C8 C7 C1 115.18(16) . . ?
C8 C7 H7 108.41(10) . . ?
H8 C8 C7 108.80(10) . . ?
C9 C8 C7 101.76(15) . . ?
C9 C8 H8 108.80(11) . . ?
C11 C8 C7 111.70(15) . . ?
C11 C8 H8 108.80(10) . . ?
C11 C8 C9 116.61(16) . . ?
H9a C9 C8 110.97(11) . . ?
H9b C9 C8 110.97(11) . . ?
H9b C9 H9a 109.0 . . ?
C10 C9 C8 103.96(16) . . ?
C10 C9 H9a 110.97(12) . . ?
C10 C9 H9b 110.97(12) . . ?
O2 C10 O1 119.7(2) . . ?
C9 C10 O1 110.66(16) . . ?
C9 C10 O2 129.7(2) . . ?
C12 C11 C8 120.45(17) . . ?
C16 C11 C8 121.07(18) . . ?
C16 C11 C12 118.42(18) . . ?
H12 C12 C11 119.40(12) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.40(14) . . ?
H13 C13 C12 120.06(14) . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.06(14) . . ?
H14 C14 C13 120.17(14) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.17(14) . . ?
H15 C15 C14 119.80(14) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.80(15) . . ?
C15 C16 C11 120.4(2) . . ?
H16 C16 C11 119.78(12) . . ?
H16 C16 C15 119.78(15) . . ?

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
O1 C7 C1 C2 -40.6(2) . . . . ?
O1 C7 C1 C6 140.35(17) . . . . ?
O1 C7 C8 C9 -29.57(16) . . . . ?
O1 C7 C8 C11 -154.69(14) . . . . ?
O1 C10 C9 C8 -9.71(19) . . . . ?
O2 C10 C9 C8 170.2(3) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C6 C5 C4 0.7(2) . . . . ?
C1 C7 C8 C9 -152.13(18) . . . . ?
C1 C7 C8 C11 82.75(18) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C7 C8 C9 C10 23.31(16) . . . . ?
C7 C8 C11 C12 -112.82(16) . . . . ?
C7 C8 C11 C16 64.40(18) . . . . ?
C8 C11 C12 C13 176.93(18) . . . . ?
C8 C11 C16 C15 -177.04(18) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C11 C16 C15 C14 0.3(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 C16 -0.8(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 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.484
####################################################################### 
# 
# 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_zhangzhangsheng_0302
_database_code_depnum_ccdc_archive 'CCDC 2164219'
loop_
_audit_author_name
_audit_author_address
'Chang-sheng Zhang'
;Lanzhou University
China
;
_audit_update_record             
;
2022-04-04 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-12-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H12 O2)'
_chemical_formula_sum            'C28 H24 O4'
_chemical_formula_weight         424.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.67930(10)
_cell_length_b                   22.7043(3)
_cell_length_c                   11.04130(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2175.77(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9071
_cell_measurement_temperature    298.23(10)
_cell_measurement_theta_max      75.3670
_cell_measurement_theta_min      1.9490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11192
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.912
_diffrn_reflns_theta_min         4.453
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.23(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 175.00   0.50    0.05    --  109.26  47.00   0.00  166
  2  ω    136.00 170.00   0.50    0.05    --  109.26  30.00 -60.00   68
  3  ω    135.00 173.00   0.50    0.05    --  109.26  45.00 -90.00   76
  4  ω     98.00 125.00   0.50    0.05    --  109.26  30.00 -60.00   54
  5  ω     44.00  70.00   0.50    0.05    --  109.26 -77.00   0.00   52
  6  ω     38.00  67.00   0.50    0.05    --  109.26 -61.00 150.00   58
  7  ω    -19.00  14.00   0.50    0.05    --   43.05 -19.00  90.00   66
  8  ω    -11.00  15.00   0.50    0.05    --   43.05 -19.00-150.00   52
  9  ω     35.00  67.00   0.50    0.05    --  109.26 -61.00-180.00   64
 10  ω    -51.00 -24.00   0.50    0.05    -- -100.00  45.00  60.00   54
 11  ω    -74.00 -27.00   0.50    0.05    -- -100.00  61.00 120.00   94
 12  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 150.00   50
 13  ω    -53.00 -24.00   0.50    0.05    -- -100.00  45.00 120.00   58
 14  ω    -51.00 -24.00   0.50    0.05    -- -100.00  45.00  90.00   54
 15  ω    -73.00 -27.00   0.50    0.05    -- -100.00  79.00 135.00   92
 16  ω   -127.00-100.00   0.50    0.05    -- -100.00  79.00 135.00   54
 17  ω    -24.00  35.00   0.50    0.05    --  -43.05  19.00 120.00  118
 18  ω    -55.00  32.00   0.50    0.05    --  -43.05  47.00   0.00  174
 19  ω    -96.00 -37.00   0.50    0.05    -- -100.00 104.00-135.00  118
 20  ω     37.00  93.00   0.50    0.05    --  109.26 -94.00-120.00  112
 21  ω   -115.00 -90.00   0.50    0.05    --  -43.05-179.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288311000
_diffrn_orient_matrix_UB_12      0.0650141000
_diffrn_orient_matrix_UB_13      -0.0330433000
_diffrn_orient_matrix_UB_21      -0.0993254000
_diffrn_orient_matrix_UB_22      -0.0073627000
_diffrn_orient_matrix_UB_23      -0.1146734000
_diffrn_orient_matrix_UB_31      -0.1441476000
_diffrn_orient_matrix_UB_32      0.0180867000
_diffrn_orient_matrix_UB_33      0.0723015000
_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         0.716
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                4025
_reflns_number_total             4292
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1591 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.066
_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)+(0.0602P)²+0.1268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00A(H00G), C00K(H00K)
1.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00C), C00Q(H00Q,H00R), C00R(H00D,H00F), C00T(H00T,H00V)
1.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00H), C00E(H00E), C00G(H00I), C00I(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00S(H00S), C00U(H00U),
 C00V(H00W), C00W(H00X)
;
_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
O001 O 0.26966(17) 0.37599(7) 0.72018(14) 0.0600(4) Uani 1 1 d . . . . .
O002 O 0.77923(19) 0.37627(7) 0.83246(15) 0.0641(4) Uani 1 1 d . . . . .
O003 O 0.2223(2) 0.45866(8) 0.82081(19) 0.0812(5) Uani 1 1 d . . . . .
C004 C 1.0080(2) 0.19377(9) 0.81799(17) 0.0486(4) Uani 1 1 d . . . . .
C005 C 0.4067(2) 0.29792(9) 0.61761(18) 0.0495(4) Uani 1 1 d . . . . .
C006 C 0.2805(2) 0.43483(10) 0.7361(2) 0.0570(5) Uani 1 1 d . . . . .
O007 O 0.6472(3) 0.45958(10) 0.8324(3) 0.1231(10) Uani 1 1 d . . . . .
C008 C 0.9206(2) 0.28923(9) 0.89232(18) 0.0490(4) Uani 1 1 d . . . . .
C009 C 0.4255(2) 0.19662(9) 0.54772(18) 0.0493(4) Uani 1 1 d . . . . .
C00A C 0.9257(2) 0.35500(9) 0.8832(2) 0.0558(5) Uani 1 1 d . . . . .
H00G H 1.008859 0.365865 0.827422 0.067 Uiso 1 1 calc R U . . .
C00B C 0.5082(3) 0.28419(10) 0.71381(18) 0.0570(5) Uani 1 1 d . . . . .
H00B H 0.536834 0.313437 0.768331 0.068 Uiso 1 1 calc R U . . .
C00C C 1.0042(2) 0.25618(9) 0.81152(19) 0.0514(4) Uani 1 1 d . . . . .
H00H H 1.059760 0.275172 0.751004 0.062 Uiso 1 1 calc R U . . .
C00D C 0.3723(3) 0.46149(10) 0.6352(2) 0.0634(6) Uani 1 1 d . . . . .
H00A H 0.446814 0.489611 0.665980 0.076 Uiso 1 1 calc R U . . .
H00C H 0.305887 0.481015 0.577097 0.076 Uiso 1 1 calc R U . . .
C00E C 0.3689(2) 0.25493(9) 0.53647(18) 0.0518(5) Uani 1 1 d . . . . .
H00E H 0.304211 0.264149 0.472036 0.062 Uiso 1 1 calc R U . . .
C00F C 0.5240(2) 0.18318(9) 0.64637(18) 0.0519(5) Uani 1 1 d . . . . .
C00G C 0.8363(3) 0.25986(11) 0.9832(2) 0.0599(5) Uani 1 1 d . . . . .
H00I H 0.778501 0.281812 1.037961 0.072 Uiso 1 1 calc R U . . .
C00H C 0.9235(2) 0.16596(10) 0.91172(18) 0.0527(5) Uani 1 1 d . . . . .
C00I C 1.0964(3) 0.15899(11) 0.7384(2) 0.0660(6) Uani 1 1 d . . . . .
H00J H 1.153064 0.177074 0.677358 0.079 Uiso 1 1 calc R U . . .
C00J C 0.7529(3) 0.43134(11) 0.8712(3) 0.0737(7) Uani 1 1 d . . . . .
C00K C 0.3408(3) 0.35855(9) 0.6054(2) 0.0567(5) Uani 1 1 d . . . . .
H00K H 0.261300 0.357970 0.542367 0.068 Uiso 1 1 calc R U . . .
C00L C 0.8375(3) 0.20064(11) 0.9926(2) 0.0612(5) Uani 1 1 d . . . . .
H00L H 0.780594 0.182498 1.053414 0.073 Uiso 1 1 calc R U . . .
C00M C 0.5750(3) 0.12416(11) 0.6602(2) 0.0677(6) Uani 1 1 d . . . . .
H00M H 0.641180 0.114651 0.723480 0.081 Uiso 1 1 calc R U . . .
C00N C 1.1001(4) 0.09960(12) 0.7495(3) 0.0778(7) Uani 1 1 d . . . . .
H00N H 1.159967 0.077415 0.696639 0.093 Uiso 1 1 calc R U . . .
C00O C 0.5644(3) 0.22860(10) 0.72737(19) 0.0592(5) Uani 1 1 d . . . . .
H00O H 0.630825 0.220430 0.791311 0.071 Uiso 1 1 calc R U . . .
C00P C 0.3811(3) 0.15119(10) 0.4670(2) 0.0645(6) Uani 1 1 d . . . . .
H00P H 0.317700 0.159800 0.401397 0.077 Uiso 1 1 calc R U . . .
C00Q C 0.8691(3) 0.44845(11) 0.9643(3) 0.0725(7) Uani 1 1 d . . . . .
H00Q H 0.820076 0.466451 1.033989 0.087 Uiso 1 1 calc R U . . .
H00R H 0.944128 0.475702 0.931035 0.087 Uiso 1 1 calc R U . . .
C00R C 0.4521(3) 0.40844(10) 0.5788(2) 0.0721(7) Uani 1 1 d . . . . .
H00D H 0.465919 0.413719 0.492303 0.087 Uiso 1 1 calc R U . . .
H00F H 0.551575 0.401398 0.616066 0.087 Uiso 1 1 calc R U . . .
C00S C 0.5285(3) 0.08115(11) 0.5819(3) 0.0764(8) Uani 1 1 d . . . . .
H00S H 0.561710 0.042576 0.592832 0.092 Uiso 1 1 calc R U . . .
C00T C 0.9439(3) 0.39059(11) 0.9979(2) 0.0699(6) Uani 1 1 d . . . . .
H00T H 1.051658 0.395906 1.018477 0.084 Uiso 1 1 calc R U . . .
H00V H 0.891217 0.372080 1.065424 0.084 Uiso 1 1 calc R U . . .
C00U C 0.4307(3) 0.09506(11) 0.4850(3) 0.0766(7) Uani 1 1 d . . . . .
H00U H 0.399217 0.065460 0.432273 0.092 Uiso 1 1 calc R U . . .
C00V C 0.9289(3) 0.10323(11) 0.9197(2) 0.0717(7) Uani 1 1 d . . . . .
H00W H 0.873643 0.083822 0.979816 0.086 Uiso 1 1 calc R U . . .
C00W C 1.0154(4) 0.07164(11) 0.8389(3) 0.0806(8) Uani 1 1 d . . . . .
H00X H 1.017363 0.030767 0.844103 0.097 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
O001 C006 1.351(3) . ?
O001 C00K 1.465(3) . ?
O002 C00A 1.471(3) . ?
O002 C00J 1.341(3) . ?
O003 C006 1.193(3) . ?
C004 C00C 1.419(3) . ?
C004 C00H 1.417(3) . ?
C004 C00I 1.409(3) . ?
C005 C00B 1.415(3) . ?
C005 C00E 1.365(3) . ?
C005 C00K 1.497(3) . ?
C006 C00D 1.497(3) . ?
O007 C00J 1.199(3) . ?
C008 C00A 1.497(3) . ?
C008 C00C 1.373(3) . ?
C008 C00G 1.410(3) . ?
C009 C00E 1.418(3) . ?
C009 C00F 1.418(3) . ?
C009 C00P 1.417(3) . ?
C00A H00G 0.9800 . ?
C00A C00T 1.511(3) . ?
C00B H00B 0.9300 . ?
C00B C00O 1.362(3) . ?
C00C H00H 0.9300 . ?
C00D H00A 0.9700 . ?
C00D H00C 0.9700 . ?
C00D C00R 1.523(3) . ?
C00E H00E 0.9300 . ?
C00F C00M 1.420(3) . ?
C00F C00O 1.409(3) . ?
C00G H00I 0.9300 . ?
C00G C00L 1.348(3) . ?
C00H C00L 1.405(3) . ?
C00H C00V 1.428(3) . ?
C00I H00J 0.9300 . ?
C00I C00N 1.354(3) . ?
C00J C00Q 1.492(4) . ?
C00K H00K 0.9800 . ?
C00K C00R 1.517(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00S 1.365(4) . ?
C00N H00N 0.9300 . ?
C00N C00W 1.384(4) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00P C00U 1.360(4) . ?
C00Q H00Q 0.9700 . ?
C00Q H00R 0.9700 . ?
C00Q C00T 1.512(4) . ?
C00R H00D 0.9700 . ?
C00R H00F 0.9700 . ?
C00S H00S 0.9300 . ?
C00S C00U 1.402(4) . ?
C00T H00T 0.9700 . ?
C00T H00V 0.9700 . ?
C00U H00U 0.9300 . ?
C00V H00W 0.9300 . ?
C00V C00W 1.369(4) . ?
C00W H00X 0.9300 . ?

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
C006 O001 C00K 110.51(16) . . ?
C00J O002 C00A 109.40(17) . . ?
C00H C004 C00C 118.02(18) . . ?
C00I C004 C00C 122.74(19) . . ?
C00I C004 C00H 119.2(2) . . ?
C00B C005 C00K 120.56(18) . . ?
C00E C005 C00B 119.01(19) . . ?
C00E C005 C00K 120.43(18) . . ?
O001 C006 C00D 109.92(18) . . ?
O003 C006 O001 121.4(2) . . ?
O003 C006 C00D 128.7(2) . . ?
C00C C008 C00A 119.06(18) . . ?
C00C C008 C00G 118.58(19) . . ?
C00G C008 C00A 122.34(19) . . ?
C00F C009 C00E 118.51(18) . . ?
C00P C009 C00E 122.0(2) . . ?
C00P C009 C00F 119.4(2) . . ?
O002 C00A C008 109.14(16) . . ?
O002 C00A H00G 108.4 . . ?
O002 C00A C00T 103.52(18) . . ?
C008 C00A H00G 108.4 . . ?
C008 C00A C00T 118.7(2) . . ?
C00T C00A H00G 108.4 . . ?
C005 C00B H00B 119.7 . . ?
C00O C00B C005 120.66(19) . . ?
C00O C00B H00B 119.7 . . ?
C004 C00C H00H 119.2 . . ?
C008 C00C C004 121.68(18) . . ?
C008 C00C H00H 119.2 . . ?
C006 C00D H00A 111.1 . . ?
C006 C00D H00C 111.1 . . ?
C006 C00D C00R 103.08(18) . . ?
H00A C00D H00C 109.1 . . ?
C00R C00D H00A 111.1 . . ?
C00R C00D H00C 111.1 . . ?
C005 C00E C009 121.80(19) . . ?
C005 C00E H00E 119.1 . . ?
C009 C00E H00E 119.1 . . ?
C009 C00F C00M 118.3(2) . . ?
C00O C00F C009 118.71(19) . . ?
C00O C00F C00M 123.0(2) . . ?
C008 C00G H00I 119.3 . . ?
C00L C00G C008 121.5(2) . . ?
C00L C00G H00I 119.3 . . ?
C004 C00H C00V 118.2(2) . . ?
C00L C00H C004 119.29(19) . . ?
C00L C00H C00V 122.5(2) . . ?
C004 C00I H00J 119.5 . . ?
C00N C00I C004 121.0(2) . . ?
C00N C00I H00J 119.5 . . ?
O002 C00J C00Q 110.3(2) . . ?
O007 C00J O002 121.0(3) . . ?
O007 C00J C00Q 128.7(3) . . ?
O001 C00K C005 109.37(17) . . ?
O001 C00K H00K 108.7 . . ?
O001 C00K C00R 103.52(17) . . ?
C005 C00K H00K 108.7 . . ?
C005 C00K C00R 117.5(2) . . ?
C00R C00K H00K 108.7 . . ?
C00G C00L C00H 121.0(2) . . ?
C00G C00L H00L 119.5 . . ?
C00H C00L H00L 119.5 . . ?
C00F C00M H00M 119.5 . . ?
C00S C00M C00F 121.0(2) . . ?
C00S C00M H00M 119.5 . . ?
C00I C00N H00N 119.7 . . ?
C00I C00N C00W 120.6(3) . . ?
C00W C00N H00N 119.7 . . ?
C00B C00O C00F 121.27(19) . . ?
C00B C00O H00O 119.4 . . ?
C00F C00O H00O 119.4 . . ?
C009 C00P H00P 119.9 . . ?
C00U C00P C009 120.3(2) . . ?
C00U C00P H00P 119.9 . . ?
C00J C00Q H00Q 111.1 . . ?
C00J C00Q H00R 111.1 . . ?
C00J C00Q C00T 103.50(19) . . ?
H00Q C00Q H00R 109.0 . . ?
C00T C00Q H00Q 111.1 . . ?
C00T C00Q H00R 111.1 . . ?
C00D C00R H00D 111.2 . . ?
C00D C00R H00F 111.2 . . ?
C00K C00R C00D 102.8(2) . . ?
C00K C00R H00D 111.2 . . ?
C00K C00R H00F 111.2 . . ?
H00D C00R H00F 109.1 . . ?
C00M C00S H00S 120.0 . . ?
C00M C00S C00U 120.1(2) . . ?
C00U C00S H00S 120.0 . . ?
C00A C00T C00Q 102.3(2) . . ?
C00A C00T H00T 111.3 . . ?
C00A C00T H00V 111.3 . . ?
C00Q C00T H00T 111.3 . . ?
C00Q C00T H00V 111.3 . . ?
H00T C00T H00V 109.2 . . ?
C00P C00U C00S 121.0(2) . . ?
C00P C00U H00U 119.5 . . ?
C00S C00U H00U 119.5 . . ?
C00H C00V H00W 120.0 . . ?
C00W C00V C00H 120.0(2) . . ?
C00W C00V H00W 120.0 . . ?
C00N C00W H00X 119.5 . . ?
C00V C00W C00N 121.0(2) . . ?
C00V C00W H00X 119.5 . . ?

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
O001 C006 C00D C00R -15.9(3) . . . . ?
O001 C00K C00R C00D -31.1(2) . . . . ?
O002 C00A C00T C00Q -32.6(2) . . . . ?
O002 C00J C00Q C00T -13.7(3) . . . . ?
O003 C006 C00D C00R 164.0(3) . . . . ?
C004 C00H C00L C00G -1.0(3) . . . . ?
C004 C00H C00V C00W 0.7(4) . . . . ?
C004 C00I C00N C00W 0.7(4) . . . . ?
C005 C00B C00O C00F 0.2(3) . . . . ?
C005 C00K C00R C00D -151.7(2) . . . . ?
C006 O001 C00K C005 148.71(17) . . . . ?
C006 O001 C00K C00R 22.7(2) . . . . ?
C006 C00D C00R C00K 28.5(3) . . . . ?
O007 C00J C00Q C00T 165.7(4) . . . . ?
C008 C00A C00T C00Q -153.7(2) . . . . ?
C008 C00G C00L C00H 0.1(3) . . . . ?
C009 C00F C00M C00S -1.2(3) . . . . ?
C009 C00F C00O C00B 1.4(3) . . . . ?
C009 C00P C00U C00S -1.2(4) . . . . ?
C00A O002 C00J O007 173.0(3) . . . . ?
C00A O002 C00J C00Q -7.6(3) . . . . ?
C00A C008 C00C C004 177.96(19) . . . . ?
C00A C008 C00G C00L -177.6(2) . . . . ?
C00B C005 C00E C009 1.6(3) . . . . ?
C00B C005 C00K O001 -52.4(3) . . . . ?
C00B C005 C00K C00R 65.2(3) . . . . ?
C00C C004 C00H C00L 1.2(3) . . . . ?
C00C C004 C00H C00V -179.0(2) . . . . ?
C00C C004 C00I C00N 178.3(2) . . . . ?
C00C C008 C00A O002 106.1(2) . . . . ?
C00C C008 C00A C00T -135.7(2) . . . . ?
C00C C008 C00G C00L 0.6(3) . . . . ?
C00E C005 C00B C00O -1.7(3) . . . . ?
C00E C005 C00K O001 127.2(2) . . . . ?
C00E C005 C00K C00R -115.3(2) . . . . ?
C00E C009 C00F C00M 177.35(19) . . . . ?
C00E C009 C00F C00O -1.5(3) . . . . ?
C00E C009 C00P C00U -176.1(2) . . . . ?
C00F C009 C00E C005 0.0(3) . . . . ?
C00F C009 C00P C00U 0.9(3) . . . . ?
C00F C00M C00S C00U 1.0(4) . . . . ?
C00G C008 C00A O002 -75.6(2) . . . . ?
C00G C008 C00A C00T 42.5(3) . . . . ?
C00G C008 C00C C004 -0.3(3) . . . . ?
C00H C004 C00C C008 -0.6(3) . . . . ?
C00H C004 C00I C00N 0.8(4) . . . . ?
C00H C00V C00W C00N 0.8(4) . . . . ?
C00I C004 C00C C008 -178.1(2) . . . . ?
C00I C004 C00H C00L 178.8(2) . . . . ?
C00I C004 C00H C00V -1.4(3) . . . . ?
C00I C00N C00W C00V -1.5(4) . . . . ?
C00J O002 C00A C008 153.1(2) . . . . ?
C00J O002 C00A C00T 25.8(3) . . . . ?
C00J C00Q C00T C00A 28.2(3) . . . . ?
C00K O001 C006 O003 175.8(2) . . . . ?
C00K O001 C006 C00D -4.3(2) . . . . ?
C00K C005 C00B C00O 177.9(2) . . . . ?
C00K C005 C00E C009 -178.00(19) . . . . ?
C00L C00H C00V C00W -179.6(2) . . . . ?
C00M C00F C00O C00B -177.4(2) . . . . ?
C00M C00S C00U C00P 0.2(4) . . . . ?
C00O C00F C00M C00S 177.7(2) . . . . ?
C00P C009 C00E C005 177.1(2) . . . . ?
C00P C009 C00F C00M 0.2(3) . . . . ?
C00P C009 C00F C00O -178.6(2) . . . . ?
C00V C00H C00L C00G 179.3(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 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.549
####################################################################### 
# 
# 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_zhangchangsheng_0918-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2164220'
loop_
_audit_author_name
_audit_author_address
'Chang-sheng Zhang'
;Lanzhou University
China
;
_audit_update_record             
;
2022-04-04 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 Br O5'
_chemical_formula_sum            'C14 H17 Br O5'
_chemical_formula_weight         345.18
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8803(2)
_cell_length_b                   9.7157(2)
_cell_length_c                   10.6212(2)
_cell_angle_alpha                94.2410(10)
_cell_angle_beta                 94.434(2)
_cell_angle_gamma                111.794(2)
_cell_volume                     748.16(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6963
_cell_measurement_temperature    303.15(10)
_cell_measurement_theta_max      76.2170
_cell_measurement_theta_min      4.1930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8578
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.451
_diffrn_reflns_theta_min         4.201
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.15(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00 119.00   0.50    0.05    --   46.32  54.00 135.00  154
  2  ω     91.00 170.00   0.50    0.05    --  104.25  54.00 135.00  158
  3  ω    142.00 173.00   0.50    0.05    --  104.25  45.00  60.00   62
  4  ω    102.00 134.00   0.50    0.05    --  104.25  45.00  60.00   64
  5  ω    132.00 173.00   0.50    0.05    --  104.25  15.00-120.00   82
  6  ω     94.00 120.00   0.50    0.05    --  104.25  15.00-120.00   52
  7  ω     95.00 121.00   0.50    0.05    --  104.25  30.00-180.00   52
  8  ω    126.00 178.00   0.50    0.05    --  104.25  30.00-180.00  104
  9  ω     92.00 176.00   0.50    0.05    --  104.25  61.00-150.00  168
 10  ω    -14.00  28.00   0.50    0.05    --   46.32 -19.00-150.00   84
 11  ω    -27.00  29.00   0.50    0.05    --   46.32 -19.00   0.00  112
 12  ω    -25.00   5.00   0.50    0.05    --   46.32 -54.00  -8.00   60
 13  ω     -7.00  44.00   0.50    0.05    --   46.32 -37.00 -90.00  102
 14  ω     34.00  64.00   0.50    0.05    --  104.25 -54.00  -8.00   60
 15  ω     51.00  88.00   0.50    0.05    --  104.25 -77.00-120.00   74
 16  ω     34.00  72.00   0.50    0.05    --  104.25 -61.00 -30.00   76
 17  ω     43.00  73.00   0.50    0.05    --  104.25 -61.00 150.00   60
 18  ω     61.00  95.00   0.50    0.05    --  104.25 -94.00 150.00   68
 19  ω     74.00 112.00   0.50    0.05    --  104.25-125.00  90.00   76
 20  ω     41.00 112.00   0.50    0.05    --  104.25-125.00  60.00  142
 21  ω     36.00 104.00   0.50    0.05    --  104.25 -94.00  90.00  136
 22  ω     32.00  93.00   0.50    0.05    --  104.25-125.00   0.00  122
 23  ω     62.00  87.00   0.50    0.05    --  104.25-125.00 -60.00   50
 24  ω     82.00 112.00   0.50    0.05    --  104.25-125.00 -90.00   60
 25  ω     37.00  92.00   0.50    0.05    --  104.25 -94.00 -60.00  110
 26  ω     41.00  99.00   0.50    0.05    --  104.25 -94.00-180.00  116
 27  ω    -69.00 -33.00   0.50    0.05    -- -102.00  61.00 -60.00   72
 28  ω    -67.00 -31.00   0.50    0.05    -- -102.00  61.00 -90.00   72
 29  ω    -67.00 -35.00   0.50    0.05    -- -102.00  61.00  90.00   64
 30  ω    -59.00 -29.00   0.50    0.05    -- -102.00  54.00 135.00   60
 31  ω    -56.00  -1.00   0.50    0.05    --  -46.32  54.00 135.00  110
 32  ω   -120.00 -94.00   0.50    0.05    -- -102.00 136.00  78.38   52
 33  ω    -68.00 -36.00   0.50    0.05    --  -46.32 -54.00  -8.00   64
 34  ω   -114.00 -89.00   0.50    0.05    --  -46.32 -54.00  -8.00   50
 35  ω   -167.00-141.00   0.50    0.05    -- -102.00 -54.00  -8.00   52
 36  ω   -140.00-106.00   0.50    0.05    -- -102.00 -54.00  -8.00   68
 37  ω   -116.00 -81.00   0.50    0.05    --  -46.32-125.00 -60.00   70
 38  ω   -159.00 -75.00   0.50    0.05    -- -102.00-125.00   0.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1447049000
_diffrn_orient_matrix_UB_12      0.1402530000
_diffrn_orient_matrix_UB_13      -0.0421787000
_diffrn_orient_matrix_UB_21      -0.1519327000
_diffrn_orient_matrix_UB_22      0.0238946000
_diffrn_orient_matrix_UB_23      -0.0850385000
_diffrn_orient_matrix_UB_31      -0.0296753000
_diffrn_orient_matrix_UB_32      0.0963515000
_diffrn_orient_matrix_UB_33      0.1114347000
_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                2761
_reflns_number_total             2995
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.068
_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)+(0.0440P)²+0.1921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;
_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 0.22018(3) 0.79121(3) 0.34692(2) 0.06327(11) Uani 1 1 d . . . . .
O1 O 0.17205(19) 0.47172(17) 0.36890(14) 0.0548(3) Uani 1 1 d . . . . .
O2 O 0.3896(2) 0.32226(15) 0.29143(15) 0.0583(4) Uani 1 1 d . . . . .
O3 O 0.6630(2) 0.44963(15) 0.15096(16) 0.0570(4) Uani 1 1 d . . . . .
O4 O 0.6538(2) 0.95228(14) 0.07842(12) 0.0480(3) Uani 1 1 d . . . . .
O5 O 0.8579(3) 1.1505(2) 0.00897(18) 0.0748(5) Uani 1 1 d . . . . .
C1 C 0.4230(3) 0.46377(19) 0.25941(18) 0.0442(4) Uani 1 1 d . . . . .
C2 C 0.5680(3) 0.5338(2) 0.18896(18) 0.0428(4) Uani 1 1 d . . . . .
C3 C 0.6063(3) 0.67970(19) 0.16398(17) 0.0429(4) Uani 1 1 d . . . . .
H3 H 0.701913 0.725356 0.116302 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5045(2) 0.75884(19) 0.20885(17) 0.0407(4) Uani 1 1 d . . . . .
C5 C 0.3609(3) 0.6878(2) 0.27910(18) 0.0432(4) Uani 1 1 d . . . . .
C6 C 0.3190(3) 0.5404(2) 0.30400(17) 0.0433(4) Uani 1 1 d . . . . .
C7 C 0.2214(4) 0.4610(4) 0.4991(2) 0.0743(7) Uani 1 1 d . . . . .
H7A H 0.286999 0.395408 0.503866 0.111 Uiso 1 1 calc R U . . .
H7B H 0.112044 0.422254 0.540739 0.111 Uiso 1 1 calc R U . . .
H7C H 0.298135 0.558116 0.540280 0.111 Uiso 1 1 calc R U . . .
C8 C 0.2866(4) 0.2058(2) 0.1944(3) 0.0693(6) Uani 1 1 d . . . . .
H8A H 0.358421 0.208652 0.124918 0.104 Uiso 1 1 calc R U . . .
H8B H 0.175676 0.218702 0.164992 0.104 Uiso 1 1 calc R U . . .
H8C H 0.255938 0.111359 0.227624 0.104 Uiso 1 1 calc R U . . .
C9 C 0.8138(3) 0.5142(2) 0.0797(2) 0.0594(5) Uani 1 1 d . . . . .
H9A H 0.770873 0.542913 0.002764 0.089 Uiso 1 1 calc R U . . .
H9B H 0.867589 0.442615 0.059247 0.089 Uiso 1 1 calc R U . . .
H9C H 0.904375 0.600501 0.129241 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5532(3) 0.92001(19) 0.18875(18) 0.0431(4) Uani 1 1 d . . . . .
H10 H 0.439527 0.938330 0.173281 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6806(3) 1.0357(2) 0.29705(19) 0.0493(4) Uani 1 1 d . . . . .
H11 H 0.607482 1.060157 0.359075 0.059 Uiso 1 1 calc R U . . .
C12 C 0.7674(3) 1.1674(2) 0.2227(2) 0.0577(5) Uani 1 1 d . . . . .
H12A H 0.693713 1.228119 0.218374 0.069 Uiso 1 1 calc R U . . .
H12B H 0.890529 1.229211 0.261495 0.069 Uiso 1 1 calc R U . . .
C13 C 0.7720(3) 1.0973(2) 0.0934(2) 0.0536(5) Uani 1 1 d . . . . .
C14 C 0.8233(4) 0.9875(3) 0.3631(2) 0.0671(6) Uani 1 1 d . . . . .
H14A H 0.763978 0.907539 0.412170 0.101 Uiso 1 1 calc R U . . .
H14B H 0.910855 1.070254 0.418284 0.101 Uiso 1 1 calc R U . . .
H14C H 0.885668 0.954148 0.300743 0.101 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 C5 1.8981(19) . ?
O1 C6 1.371(2) . ?
O1 C7 1.430(3) . ?
O2 C1 1.375(2) . ?
O2 C8 1.421(3) . ?
O3 C2 1.358(2) . ?
O3 C9 1.426(3) . ?
O4 C10 1.454(2) . ?
O4 C13 1.359(2) . ?
O5 C13 1.196(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.386(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 C5 1.393(3) . ?
C4 C10 1.504(2) . ?
C5 C6 1.395(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.545(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.521(3) . ?
C11 C14 1.514(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.497(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C6 O1 C7 114.14(16) . . ?
C1 O2 C8 114.74(17) . . ?
C2 O3 C9 118.42(15) . . ?
C13 O4 C10 109.65(15) . . ?
O2 C1 C2 120.57(18) . . ?
O2 C1 C6 119.40(17) . . ?
C6 C1 C2 119.92(16) . . ?
O3 C2 C1 115.32(16) . . ?
O3 C2 C3 124.93(17) . . ?
C3 C2 C1 119.74(17) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.16(17) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.41(16) . . ?
C3 C4 C10 121.21(16) . . ?
C5 C4 C10 120.30(16) . . ?
C4 C5 Br1 120.57(14) . . ?
C4 C5 C6 121.26(17) . . ?
C6 C5 Br1 118.16(14) . . ?
O1 C6 C1 120.66(17) . . ?
O1 C6 C5 119.81(18) . . ?
C1 C6 C5 119.50(17) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 C4 109.46(14) . . ?
O4 C10 H10 108.9 . . ?
O4 C10 C11 104.32(15) . . ?
C4 C10 H10 108.9 . . ?
C4 C10 C11 116.12(15) . . ?
C11 C10 H10 108.9 . . ?
C10 C11 H11 110.2 . . ?
C12 C11 C10 100.09(16) . . ?
C12 C11 H11 110.2 . . ?
C14 C11 C10 113.77(17) . . ?
C14 C11 H11 110.2 . . ?
C14 C11 C12 111.99(19) . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 C11 104.19(16) . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
O4 C13 C12 109.45(18) . . ?
O5 C13 O4 120.6(2) . . ?
O5 C13 C12 130.0(2) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C5 C6 O1 4.1(2) . . . . ?
Br1 C5 C6 C1 -177.90(14) . . . . ?
O2 C1 C2 O3 3.2(3) . . . . ?
O2 C1 C2 C3 -176.21(17) . . . . ?
O2 C1 C6 O1 -6.5(3) . . . . ?
O2 C1 C6 C5 175.53(17) . . . . ?
O3 C2 C3 C4 -178.60(18) . . . . ?
O4 C10 C11 C12 34.04(19) . . . . ?
O4 C10 C11 C14 -85.6(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 O1 177.47(17) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C10 176.17(17) . . . . ?
C3 C4 C5 Br1 178.40(14) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C10 O4 24.4(2) . . . . ?
C3 C4 C10 C11 -93.3(2) . . . . ?
C4 C5 C6 O1 -177.28(16) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C10 C11 C12 154.58(17) . . . . ?
C4 C10 C11 C14 35.0(3) . . . . ?
C5 C4 C10 O4 -158.90(16) . . . . ?
C5 C4 C10 C11 83.4(2) . . . . ?
C6 C1 C2 O3 179.21(17) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 O1 C6 C1 79.2(3) . . . . ?
C7 O1 C6 C5 -102.8(2) . . . . ?
C8 O2 C1 C2 -82.1(2) . . . . ?
C8 O2 C1 C6 101.9(2) . . . . ?
C9 O3 C2 C1 -179.45(19) . . . . ?
C9 O3 C2 C3 -0.1(3) . . . . ?
C10 O4 C13 O5 -174.0(2) . . . . ?
C10 O4 C13 C12 4.8(2) . . . . ?
C10 C4 C5 Br1 1.7(2) . . . . ?
C10 C4 C5 C6 -176.94(17) . . . . ?
C10 C11 C12 C13 -30.9(2) . . . . ?
C11 C12 C13 O4 17.8(2) . . . . ?
C11 C12 C13 O5 -163.5(2) . . . . ?
C13 O4 C10 C4 -150.08(16) . . . . ?
C13 O4 C10 C11 -25.19(19) . . . . ?
C14 C11 C12 C13 90.0(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 3.745
_oxdiff_exptl_absorpt_empirical_full_min 0.575
