# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20191125_kimaru
_database_code_depnum_ccdc_archive 'CCDC 2057420'
loop_
_audit_author_name
_audit_author_address
'Natsuki Kimaru'
;Keio University
Japan
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Br O'
_chemical_formula_iupac          ?
_chemical_formula_weight         307.22

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   6.7413(5)
_cell_length_b                   11.0630(8)
_cell_length_c                   11.1739(8)
_cell_angle_alpha                65.911(2)
_cell_angle_beta                 76.843(3)
_cell_angle_gamma                81.307(3)
_cell_volume                     739.20(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3987
_cell_measurement_theta_min      3.3771
_cell_measurement_theta_max      25.0578
_cell_measurement_temperature    253.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.870
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.260
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316

_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.23
_exptl_absorpt_correction_T_max  0.53

_exptl_special_details           
;
;

_diffrn_ambient_temperature      253.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            6595
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2467
_reflns_number_gt                2156
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1500
_refine_ls_goodness_of_fit_ref   1.530
_refine_ls_restrained_S_all      1.530
_refine_ls_number_reflns         2467
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.650
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.87230(5) 1.01138(4) 0.21779(4) 0.0752(3) Uani d . . . 1 . .
O O1 0.2317(4) 0.3870(2) 0.43475(19) 0.0497(6) Uani d . . . 1 . .
H H1 0.2142 0.4474 0.4615 0.075 Uiso calc U . R 1 . .
C C1 0.1565(4) 0.4317(3) 0.3114(3) 0.0395(6) Uani d . . . 1 . .
C C2 0.2537(5) 0.5589(3) 0.2158(3) 0.0439(7) Uani d . . . 1 . .
H H2 0.4002 0.5465 0.184 0.053 Uiso calc U . R 1 . .
C C3 0.3545(5) 0.7700(3) 0.2252(3) 0.0464(7) Uani d . . . 1 . .
C C4 -0.0687(5) 0.4550(3) 0.3408(3) 0.0454(7) Uani d . . . 1 . .
C C5 0.2142(5) 0.3169(3) 0.2619(3) 0.0475(7) Uani d . . . 1 . .
C C6 0.6619(5) 0.9147(3) 0.2194(4) 0.0532(8) Uani d . . . 1 . .
C C7 0.1926(5) 0.6881(3) 0.2355(3) 0.0461(7) Uani d . . . 1 . .
H H7 0.0733 0.6851 0.3056 0.055 Uiso calc U . R 1 . .
C C8 0.3515(5) 0.8082(4) 0.3298(3) 0.0557(8) Uani d . . . 1 . .
H H8 0.2447 0.7849 0.4026 0.067 Uiso calc U . R 1 . .
C C9 0.1489(6) 0.6718(4) 0.1174(3) 0.0608(9) Uani d . . . 1 . .
H H9A 0.0081 0.6636 0.1165 0.073 Uiso calc U . R 1 . .
H H9B 0.2296 0.7193 0.0307 0.073 Uiso calc U . R 1 . .
C C10 0.6655(6) 0.8818(4) 0.1136(4) 0.0675(10) Uani d . . . 1 . .
H H10 0.7706 0.907 0.0398 0.081 Uiso calc U . R 1 . .
C C11 -0.2455(5) 0.4743(4) 0.3610(4) 0.0653(10) Uani d . . . 1 . .
H H11 -0.3867 0.4897 0.3772 0.078 Uiso calc U . R 1 . .
C C12 0.5038(6) 0.8802(4) 0.3278(3) 0.0606(9) Uani d . . . 1 . .
H H12 0.4998 0.905 0.3985 0.073 Uiso calc U . R 1 . .
C C13 0.1404(7) 0.3538(4) 0.1310(3) 0.0671(10) Uani d . . . 1 . .
H H13A 0.2029 0.4321 0.0648 0.101 Uiso calc U . R 1 . .
H H13B -0.0053 0.3703 0.1449 0.101 Uiso calc U . R 1 . .
H H13C 0.1771 0.282 0.1012 0.101 Uiso calc U . R 1 . .
C C14 0.5104(6) 0.8107(4) 0.1177(4) 0.0652(10) Uani d . . . 1 . .
H H14 0.5119 0.7896 0.045 0.078 Uiso calc U . R 1 . .
C C15 0.4452(6) 0.2872(4) 0.2396(4) 0.0661(10) Uani d . . . 1 . .
H H15A 0.4936 0.2682 0.3203 0.099 Uiso calc U . R 1 . .
H H15B 0.5095 0.3629 0.1695 0.099 Uiso calc U . R 1 . .
H H15C 0.4778 0.2119 0.215 0.099 Uiso calc U . R 1 . .
C C16 0.1133(7) 0.1904(4) 0.3667(4) 0.0651(10) Uani d . . . 1 . .
H H16A 0.1542 0.1186 0.3372 0.098 Uiso calc U . R 1 . .
H H16B -0.0325 0.2061 0.3779 0.098 Uiso calc U . R 1 . .
H H16C 0.1552 0.1679 0.4502 0.098 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C6 . 1.894(3) ?
O1 C1 . 1.445(3) ?
O1 H1 . 0.82 ?
C1 C4 . 1.484(4) ?
C1 C2 . 1.511(4) ?
C1 C5 . 1.548(4) ?
C2 C9 . 1.494(5) ?
C2 C7 . 1.517(4) ?
C2 H2 . 0.98 ?
C3 C14 . 1.370(5) ?
C3 C8 . 1.391(5) ?
C3 C7 . 1.477(5) ?
C4 C11 . 1.165(5) ?
C5 C13 . 1.528(4) ?
C5 C15 . 1.527(5) ?
C5 C16 . 1.542(5) ?
C6 C10 . 1.366(6) ?
C6 C12 . 1.381(5) ?
C7 C9 . 1.499(5) ?
C7 H7 . 0.98 ?
C8 C12 . 1.382(5) ?
C8 H8 . 0.93 ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C14 . 1.383(6) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 109.5 ?
O1 C1 C4 . . 108.2(2) ?
O1 C1 C2 . . 108.3(2) ?
C4 C1 C2 . . 110.5(3) ?
O1 C1 C5 . . 105.8(2) ?
C4 C1 C5 . . 110.4(2) ?
C2 C1 C5 . . 113.3(2) ?
C9 C2 C1 . . 124.4(3) ?
C9 C2 C7 . . 59.7(2) ?
C1 C2 C7 . . 121.5(2) ?
C9 C2 H2 . . 113.6 ?
C1 C2 H2 . . 113.6 ?
C7 C2 H2 . . 113.6 ?
C14 C3 C8 . . 117.4(3) ?
C14 C3 C7 . . 123.6(3) ?
C8 C3 C7 . . 119.0(3) ?
C11 C4 C1 . . 178.6(3) ?
C13 C5 C15 . . 109.0(3) ?
C13 C5 C16 . . 108.7(3) ?
C15 C5 C16 . . 108.6(3) ?
C13 C5 C1 . . 110.1(3) ?
C15 C5 C1 . . 110.5(3) ?
C16 C5 C1 . . 109.9(3) ?
C10 C6 C12 . . 120.7(3) ?
C10 C6 Br1 . . 120.2(3) ?
C12 C6 Br1 . . 119.0(3) ?
C3 C7 C9 . . 122.9(3) ?
C3 C7 C2 . . 118.8(3) ?
C9 C7 C2 . . 59.4(2) ?
C3 C7 H7 . . 114.8 ?
C9 C7 H7 . . 114.8 ?
C2 C7 H7 . . 114.8 ?
C12 C8 C3 . . 121.4(3) ?
C12 C8 H8 . . 119.3 ?
C3 C8 H8 . . 119.3 ?
C2 C9 C7 . . 60.9(2) ?
C2 C9 H9A . . 117.7 ?
C7 C9 H9A . . 117.7 ?
C2 C9 H9B . . 117.7 ?
C7 C9 H9B . . 117.7 ?
H9A C9 H9B . . 114.8 ?
C6 C10 C14 . . 119.0(3) ?
C6 C10 H10 . . 120.5 ?
C14 C10 H10 . . 120.5 ?
C4 C11 H11 . . 180.0 ?
C8 C12 C6 . . 119.1(3) ?
C8 C12 H12 . . 120.5 ?
C6 C12 H12 . . 120.5 ?
C5 C13 H13A . . 109.5 ?
C5 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C5 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C10 C14 C3 . . 122.3(3) ?
C10 C14 H14 . . 118.8 ?
C3 C14 H14 . . 118.8 ?
C5 C15 H15A . . 109.5 ?
C5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C5 C16 H16A . . 109.5 ?
C5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C9 . . . . -144.8(3) ?
C4 C1 C2 C9 . . . . -26.4(4) ?
C5 C1 C2 C9 . . . . 98.2(3) ?
O1 C1 C2 C7 . . . . -72.1(3) ?
C4 C1 C2 C7 . . . . 46.3(3) ?
C5 C1 C2 C7 . . . . 170.9(3) ?
O1 C1 C5 C13 . . . . 179.8(3) ?
C4 C1 C5 C13 . . . . 62.9(4) ?
C2 C1 C5 C13 . . . . -61.7(3) ?
O1 C1 C5 C15 . . . . -59.7(3) ?
C4 C1 C5 C15 . . . . -176.6(3) ?
C2 C1 C5 C15 . . . . 58.8(3) ?
O1 C1 C5 C16 . . . . 60.0(3) ?
C4 C1 C5 C16 . . . . -56.9(3) ?
C2 C1 C5 C16 . . . . 178.6(3) ?
C14 C3 C7 C9 . . . . -17.0(5) ?
C8 C3 C7 C9 . . . . 163.4(3) ?
C14 C3 C7 C2 . . . . 53.4(5) ?
C8 C3 C7 C2 . . . . -126.3(3) ?
C9 C2 C7 C3 . . . . -113.2(3) ?
C1 C2 C7 C3 . . . . 132.6(3) ?
C1 C2 C7 C9 . . . . -114.1(3) ?
C14 C3 C8 C12 . . . . -2.4(6) ?
C7 C3 C8 C12 . . . . 177.3(3) ?
C1 C2 C9 C7 . . . . 109.5(3) ?
C3 C7 C9 C2 . . . . 106.5(3) ?
C12 C6 C10 C14 . . . . -1.4(6) ?
Br1 C6 C10 C14 . . . . 179.7(3) ?
C3 C8 C12 C6 . . . . 0.1(6) ?
C10 C6 C12 C8 . . . . 1.9(6) ?
Br1 C6 C12 C8 . . . . -179.2(3) ?
C6 C10 C14 C3 . . . . -1.0(7) ?
C8 C3 C14 C10 . . . . 2.9(6) ?
C7 C3 C14 C10 . . . . -176.8(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_20210118retry
_database_code_depnum_ccdc_archive 'CCDC 2057422'
loop_
_audit_author_name
_audit_author_address
'Natsuki Kimaru'
;Keio University
Japan
;
_audit_update_record             
;
2021-01-20 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         214.29

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.0860(5)
_cell_length_b                   10.8034(3)
_cell_length_c                   12.6109(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.2260(10)
_cell_angle_gamma                90
_cell_volume                     2627.52(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.5261
_cell_measurement_theta_max      25.0715
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            24837
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             4612
_reflns_number_gt                3693
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1888
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_number_reflns         4612
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.7858P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.66731(8) 0.30041(12) 0.80401(11) 0.0539(4) Uani d . . . 1 . .
H H1 0.708347 0.296821 0.805572 0.081 Uiso calc U . R 1 . .
O O2 0.78587(8) 0.18244(14) 0.72446(11) 0.0568(4) Uani d . . . 1 . .
H H2 0.746393 0.166442 0.687001 0.085 Uiso calc U . R 1 . .
C C1 0.81976(10) 0.01303(17) 0.62946(15) 0.0444(4) Uani d . . . 1 . .
H H1A 0.828958 -0.046418 0.690542 0.053 Uiso calc U . R 1 . .
C C2 0.83001(10) -0.03812(18) 0.52382(16) 0.0486(5) Uani d . . . 1 . .
H H2A 0.844736 0.023152 0.477691 0.058 Uiso calc U . R 1 . .
C C3 0.63194(10) 0.38592(16) 0.71960(15) 0.0452(4) Uani d . . . 1 . .
C C4 0.66887(11) 0.50848(17) 0.74138(16) 0.0493(5) Uani d . . . 1 . .
H H4 0.667823 0.54604 0.81163 0.059 Uiso calc U . R 1 . .
C C5 0.63256(11) 0.33547(17) 0.61125(17) 0.0510(5) Uani d . . . 1 . .
C C6 0.82615(10) 0.22892(18) 0.56908(16) 0.0493(5) Uani d . . . 1 . .
C C7 0.83474(10) 0.14661(17) 0.66519(15) 0.0444(4) Uani d . . . 1 . .
C C8 0.75841(10) -0.0175(2) 0.53579(17) 0.0542(5) Uani d . . . 1 . .
H H8A 0.731624 0.050781 0.495249 0.065 Uiso calc U . R 1 . .
H H8B 0.731424 -0.089835 0.543016 0.065 Uiso calc U . R 1 . .
C C9 0.67063(11) 0.60191(18) 0.65411(18) 0.0532(5) Uani d . . . 1 . .
H H9 0.648741 0.574773 0.578204 0.064 Uiso calc U . R 1 . .
C C10 0.85689(10) -0.16466(18) 0.51726(17) 0.0515(5) Uani d . . . 1 . .
C C11 0.73481(12) 0.5316(2) 0.7127(2) 0.0655(6) Uani d . . . 1 . .
H H11A 0.751031 0.468068 0.671633 0.079 Uiso calc U . R 1 . .
H H11B 0.771154 0.576304 0.765816 0.079 Uiso calc U . R 1 . .
C C12 0.81807(13) 0.2927(2) 0.49091(19) 0.0643(6) Uani d . . . 1 . .
H H12 0.81168 0.343177 0.429112 0.077 Uiso calc U . R 1 . .
C C13 0.66157(11) 0.73504(19) 0.6748(2) 0.0613(6) Uani d . . . 1 . .
C C14 0.90722(11) 0.1618(2) 0.74653(18) 0.0599(6) Uani d . . . 1 . .
H H14 0.908267 0.111224 0.811493 0.072 Uiso calc U . R 1 . .
C C15 0.63611(14) 0.2971(2) 0.5263(2) 0.0702(7) Uani d . . . 1 . .
H H15 0.638933 0.266509 0.458756 0.084 Uiso calc U . R 1 . .
C C16 0.84032(13) -0.2637(2) 0.5744(2) 0.0655(6) Uani d . . . 1 . .
H H16 0.812126 -0.250752 0.620673 0.079 Uiso calc U . R 1 . .
C C17 0.55718(12) 0.3954(2) 0.7293(2) 0.0638(6) Uani d . . . 1 . .
H H17 0.55968 0.428669 0.802607 0.077 Uiso calc U . R 1 . .
C C18 0.89889(13) -0.1882(2) 0.4493(2) 0.0676(6) Uani d . . . 1 . .
H H18 0.911413 -0.123444 0.41024 0.081 Uiso calc U . R 1 . .
C C19 0.86472(14) -0.3815(2) 0.5644(2) 0.0765(7) Uani d . . . 1 . .
H H19 0.852807 -0.446638 0.603814 0.092 Uiso calc U . R 1 . .
C C20 0.96317(13) 0.1121(3) 0.6981(3) 0.0881(8) Uani d . . . 1 . .
H H20A 0.960162 0.153039 0.629391 0.132 Uiso calc U . R 1 . .
H H20B 0.956787 0.024715 0.685696 0.132 Uiso calc U . R 1 . .
H H20C 1.007925 0.127223 0.748774 0.132 Uiso calc U . R 1 . .
C C21 0.92164(16) 0.2943(3) 0.7861(2) 0.0876(8) Uani d . . . 1 . .
H H21A 0.963179 0.297023 0.846499 0.131 Uiso calc U . R 1 . .
H H21B 0.883413 0.324942 0.810228 0.131 Uiso calc U . R 1 . .
H H21C 0.927443 0.34485 0.72673 0.131 Uiso calc U . R 1 . .
C C22 0.61525(14) 0.8049(2) 0.5970(3) 0.0864(9) Uani d . . . 1 . .
H H22 0.590615 0.769447 0.530452 0.104 Uiso calc U . R 1 . .
C C23 0.92259(15) -0.3067(3) 0.4386(3) 0.0846(8) Uani d . . . 1 . .
H H23 0.949898 -0.320774 0.391202 0.101 Uiso calc U . R 1 . .
C C24 0.90628(14) -0.4029(2) 0.4970(3) 0.0810(8) Uani d . . . 1 . .
H H24 0.923208 -0.481956 0.490912 0.097 Uiso calc U . R 1 . .
C C25 0.69681(15) 0.7926(2) 0.7720(3) 0.0813(8) Uani d . . . 1 . .
H H25 0.728496 0.747459 0.826068 0.098 Uiso calc U . R 1 . .
C C26 0.52118(14) 0.2699(3) 0.7190(3) 0.0913(9) Uani d . . . 1 . .
H H26A 0.475454 0.280144 0.727417 0.137 Uiso calc U . R 1 . .
H H26B 0.547436 0.215351 0.775395 0.137 Uiso calc U . R 1 . .
H H26C 0.517986 0.235151 0.647671 0.137 Uiso calc U . R 1 . .
C C27 0.60518(19) 0.9305(3) 0.6184(4) 0.1156(14) Uani d . . . 1 . .
H H27 0.573587 0.977554 0.565875 0.139 Uiso calc U . R 1 . .
C C28 0.6412(2) 0.9836(3) 0.7152(5) 0.1195(16) Uani d . . . 1 . .
H H28 0.634646 1.066696 0.728497 0.143 Uiso calc U . R 1 . .
C C29 0.6859(2) 0.9161(3) 0.7906(4) 0.1074(12) Uani d . . . 1 . .
H H29 0.710217 0.952456 0.856899 0.129 Uiso calc U . R 1 . .
C C30 0.51162(17) 0.4789(3) 0.6457(3) 0.1111(12) Uani d . . . 1 . .
H H30A 0.50563 0.445338 0.573201 0.167 Uiso calc U . R 1 . .
H H30B 0.53263 0.559299 0.650158 0.167 Uiso calc U . R 1 . .
H H30C 0.467281 0.485977 0.660065 0.167 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 . 1.438(2) ?
O1 H1 . 0.82 ?
O2 C7 . 1.443(2) ?
O2 H2 . 0.82 ?
C1 C8 . 1.486(3) ?
C1 C2 . 1.508(3) ?
C1 C7 . 1.517(3) ?
C1 H1A . 0.98 ?
C2 C10 . 1.481(3) ?
C2 C8 . 1.504(3) ?
C2 H2A . 0.98 ?
C3 C5 . 1.474(3) ?
C3 C4 . 1.505(3) ?
C3 C17 . 1.544(3) ?
C4 C11 . 1.488(3) ?
C4 C9 . 1.501(3) ?
C4 H4 . 0.98 ?
C5 C15 . 1.169(3) ?
C6 C12 . 1.176(3) ?
C6 C7 . 1.474(3) ?
C7 C14 . 1.538(3) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C13 . 1.482(3) ?
C9 C11 . 1.501(3) ?
C9 H9 . 0.98 ?
C10 C16 . 1.382(3) ?
C10 C18 . 1.384(3) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 H12 . 0.93 ?
C13 C22 . 1.374(3) ?
C13 C25 . 1.380(4) ?
C14 C21 . 1.517(3) ?
C14 C20 . 1.519(4) ?
C14 H14 . 0.98 ?
C15 H15 . 0.93 ?
C16 C19 . 1.383(3) ?
C16 H16 . 0.93 ?
C17 C30 . 1.491(4) ?
C17 C26 . 1.525(4) ?
C17 H17 . 0.98 ?
C18 C23 . 1.385(3) ?
C18 H18 . 0.93 ?
C19 C24 . 1.368(4) ?
C19 H19 . 0.93 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 C27 . 1.409(5) ?
C22 H22 . 0.93 ?
C23 C24 . 1.366(4) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
C25 C29 . 1.382(4) ?
C25 H25 . 0.93 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C27 C28 . 1.359(6) ?
C27 H27 . 0.93 ?
C28 C29 . 1.328(6) ?
C28 H28 . 0.93 ?
C29 H29 . 0.93 ?
C30 H30A . 0.96 ?
C30 H30B . 0.96 ?
C30 H30C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 H1 . . 109.5 ?
C7 O2 H2 . . 109.5 ?
C8 C1 C2 . . 60.28(13) ?
C8 C1 C7 . . 119.91(16) ?
C2 C1 C7 . . 123.10(16) ?
C8 C1 H1A . . 114.3 ?
C2 C1 H1A . . 114.3 ?
C7 C1 H1A . . 114.3 ?
C10 C2 C8 . . 121.10(17) ?
C10 C2 C1 . . 121.97(17) ?
C8 C2 C1 . . 59.12(13) ?
C10 C2 H2A . . 114.5 ?
C8 C2 H2A . . 114.5 ?
C1 C2 H2A . . 114.5 ?
O1 C3 C5 . . 108.55(14) ?
O1 C3 C4 . . 108.29(16) ?
C5 C3 C4 . . 111.29(16) ?
O1 C3 C17 . . 105.91(15) ?
C5 C3 C17 . . 110.99(18) ?
C4 C3 C17 . . 111.58(15) ?
C11 C4 C9 . . 60.28(14) ?
C11 C4 C3 . . 122.02(17) ?
C9 C4 C3 . . 124.69(17) ?
C11 C4 H4 . . 113.3 ?
C9 C4 H4 . . 113.3 ?
C3 C4 H4 . . 113.3 ?
C15 C5 C3 . . 177.0(2) ?
C12 C6 C7 . . 178.4(2) ?
O2 C7 C6 . . 108.89(15) ?
O2 C7 C1 . . 107.57(15) ?
C6 C7 C1 . . 111.21(15) ?
O2 C7 C14 . . 106.27(15) ?
C6 C7 C14 . . 110.84(16) ?
C1 C7 C14 . . 111.84(16) ?
C1 C8 C2 . . 60.59(13) ?
C1 C8 H8A . . 117.7 ?
C2 C8 H8A . . 117.7 ?
C1 C8 H8B . . 117.7 ?
C2 C8 H8B . . 117.7 ?
H8A C8 H8B . . 114.8 ?
C13 C9 C11 . . 122.3(2) ?
C13 C9 C4 . . 119.61(18) ?
C11 C9 C4 . . 59.43(14) ?
C13 C9 H9 . . 114.8 ?
C11 C9 H9 . . 114.8 ?
C4 C9 H9 . . 114.8 ?
C16 C10 C18 . . 117.3(2) ?
C16 C10 C2 . . 122.74(18) ?
C18 C10 C2 . . 119.95(19) ?
C4 C11 C9 . . 60.29(13) ?
C4 C11 H11A . . 117.7 ?
C9 C11 H11A . . 117.7 ?
C4 C11 H11B . . 117.7 ?
C9 C11 H11B . . 117.7 ?
H11A C11 H11B . . 114.9 ?
C6 C12 H12 . . 180.0 ?
C22 C13 C25 . . 117.6(2) ?
C22 C13 C9 . . 120.0(2) ?
C25 C13 C9 . . 122.4(2) ?
C21 C14 C20 . . 111.8(2) ?
C21 C14 C7 . . 112.23(19) ?
C20 C14 C7 . . 111.30(19) ?
C21 C14 H14 . . 107.1 ?
C20 C14 H14 . . 107.1 ?
C7 C14 H14 . . 107.1 ?
C5 C15 H15 . . 180.0 ?
C10 C16 C19 . . 121.5(2) ?
C10 C16 H16 . . 119.3 ?
C19 C16 H16 . . 119.3 ?
C30 C17 C26 . . 107.2(3) ?
C30 C17 C3 . . 113.7(2) ?
C26 C17 C3 . . 112.50(18) ?
C30 C17 H17 . . 107.7 ?
C26 C17 H17 . . 107.7 ?
C3 C17 H17 . . 107.7 ?
C10 C18 C23 . . 121.1(2) ?
C10 C18 H18 . . 119.5 ?
C23 C18 H18 . . 119.5 ?
C24 C19 C16 . . 120.4(2) ?
C24 C19 H19 . . 119.8 ?
C16 C19 H19 . . 119.8 ?
C14 C20 H20A . . 109.5 ?
C14 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C14 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C14 C21 H21A . . 109.5 ?
C14 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C14 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C13 C22 C27 . . 119.8(3) ?
C13 C22 H22 . . 120.1 ?
C27 C22 H22 . . 120.1 ?
C24 C23 C18 . . 120.7(2) ?
C24 C23 H23 . . 119.7 ?
C18 C23 H23 . . 119.7 ?
C23 C24 C19 . . 119.1(2) ?
C23 C24 H24 . . 120.4 ?
C19 C24 H24 . . 120.4 ?
C13 C25 C29 . . 121.2(3) ?
C13 C25 H25 . . 119.4 ?
C29 C25 H25 . . 119.4 ?
C17 C26 H26A . . 109.5 ?
C17 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C17 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C28 C27 C22 . . 120.6(3) ?
C28 C27 H27 . . 119.7 ?
C22 C27 H27 . . 119.7 ?
C29 C28 C27 . . 119.7(3) ?
C29 C28 H28 . . 120.2 ?
C27 C28 H28 . . 120.2 ?
C28 C29 C25 . . 121.1(4) ?
C28 C29 H29 . . 119.5 ?
C25 C29 H29 . . 119.5 ?
C17 C30 H30A . . 109.5 ?
C17 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C17 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C1 C2 C10 . . . . -109.6(2) ?
C7 C1 C2 C10 . . . . 142.10(19) ?
C7 C1 C2 C8 . . . . -108.3(2) ?
O1 C3 C4 C11 . . . . 78.0(2) ?
C5 C3 C4 C11 . . . . -41.3(2) ?
C17 C3 C4 C11 . . . . -165.84(19) ?
O1 C3 C4 C9 . . . . 151.82(17) ?
C5 C3 C4 C9 . . . . 32.6(3) ?
C17 C3 C4 C9 . . . . -92.0(2) ?
C8 C1 C7 O2 . . . . 75.1(2) ?
C2 C1 C7 O2 . . . . 147.20(17) ?
C8 C1 C7 C6 . . . . -44.0(2) ?
C2 C1 C7 C6 . . . . 28.0(2) ?
C8 C1 C7 C14 . . . . -168.56(17) ?
C2 C1 C7 C14 . . . . -96.5(2) ?
C7 C1 C8 C2 . . . . 113.40(19) ?
C10 C2 C8 C1 . . . . 111.1(2) ?
C11 C4 C9 C13 . . . . -112.3(2) ?
C3 C4 C9 C13 . . . . 137.4(2) ?
C3 C4 C9 C11 . . . . -110.3(2) ?
C8 C2 C10 C16 . . . . -34.5(3) ?
C1 C2 C10 C16 . . . . 36.2(3) ?
C8 C2 C10 C18 . . . . 143.6(2) ?
C1 C2 C10 C18 . . . . -145.7(2) ?
C3 C4 C11 C9 . . . . 114.6(2) ?
C13 C9 C11 C4 . . . . 107.8(2) ?
C11 C9 C13 C22 . . . . 158.2(2) ?
C4 C9 C13 C22 . . . . -131.2(2) ?
C11 C9 C13 C25 . . . . -23.7(3) ?
C4 C9 C13 C25 . . . . 46.9(3) ?
O2 C7 C14 C21 . . . . -60.7(2) ?
C6 C7 C14 C21 . . . . 57.5(3) ?
C1 C7 C14 C21 . . . . -177.8(2) ?
O2 C7 C14 C20 . . . . 173.16(19) ?
C6 C7 C14 C20 . . . . -68.7(2) ?
C1 C7 C14 C20 . . . . 56.0(2) ?
C18 C10 C16 C19 . . . . 0.1(4) ?
C2 C10 C16 C19 . . . . 178.3(2) ?
O1 C3 C17 C30 . . . . -178.7(2) ?
C5 C3 C17 C30 . . . . -61.1(3) ?
C4 C3 C17 C30 . . . . 63.6(3) ?
O1 C3 C17 C26 . . . . -56.6(3) ?
C5 C3 C17 C26 . . . . 61.0(3) ?
C4 C3 C17 C26 . . . . -174.3(2) ?
C16 C10 C18 C23 . . . . 0.6(4) ?
C2 C10 C18 C23 . . . . -177.6(2) ?
C10 C16 C19 C24 . . . . 0.0(4) ?
C25 C13 C22 C27 . . . . -0.2(4) ?
C9 C13 C22 C27 . . . . 178.0(2) ?
C10 C18 C23 C24 . . . . -1.5(4) ?
C18 C23 C24 C19 . . . . 1.5(5) ?
C16 C19 C24 C23 . . . . -0.8(4) ?
C22 C13 C25 C29 . . . . 0.1(4) ?
C9 C13 C25 C29 . . . . -178.1(2) ?
C13 C22 C27 C28 . . . . 0.4(5) ?
C22 C27 C28 C29 . . . . -0.6(5) ?
C27 C28 C29 C25 . . . . 0.5(5) ?
C13 C25 C29 C28 . . . . -0.2(5) ?

