# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_BHB1-231
_database_code_depnum_ccdc_archive 'CCDC 1897077'
loop_
_audit_author_name
_audit_author_address
'Eduardo Escudero'
;Institute of Chemical Research of Catalonia
Spain
;
_audit_update_record             
;
2019-02-13 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16'
_chemical_formula_weight         268.34
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'

_symmetry_cell_setting           Orthorhombic
_space_group_IT_number           33
_symmetry_space_group_name_H-M   Pna2(1)
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.6579(7)
_cell_length_b                   19.8384(11)
_cell_length_c                   5.6765(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1425.44(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '0.3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            21744
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.908
_diffrn_reflns_theta_max         31.184
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4210
_reflns_number_gt                3835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+0.2419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   2.9(10)
_refine_ls_number_reflns         4210
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.34039(13) 0.14580(8) 0.3481(3) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.28818(14) 0.13891(11) 0.5643(3) 0.0357(4) Uani 1 1 d . . . . .
H2 H 0.2512 0.1762 0.6297 0.043 Uiso 1 1 calc R U . . .
C3 C 0.29030(16) 0.07749(12) 0.6837(4) 0.0428(5) Uani 1 1 d . . . . .
H3 H 0.2547 0.0732 0.8303 0.051 Uiso 1 1 calc R U . . .
C4 C 0.34371(18) 0.02286(11) 0.5905(5) 0.0471(5) Uani 1 1 d . . . . .
H4 H 0.3437 -0.0191 0.6714 0.056 Uiso 1 1 calc R U . . .
C5 C 0.39717(17) 0.02944(10) 0.3792(4) 0.0425(5) Uani 1 1 d . . . . .
H5 H 0.4350 -0.0078 0.3162 0.051 Uiso 1 1 calc R U . . .
C6 C 0.39570(13) 0.09054(9) 0.2587(4) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.4328 0.0947 0.1139 0.039 Uiso 1 1 calc R U . . .
C7 C 0.33800(12) 0.20971(8) 0.2113(3) 0.0268(3) Uani 1 1 d . . . . .
H7 H 0.3741 0.2084 0.0547 0.032 Uiso 1 1 calc R U . . .
C8 C 0.34212(14) 0.27724(9) 0.3406(3) 0.0300(3) Uani 1 1 d . . . . .
H8 H 0.3439 0.2746 0.5165 0.036 Uiso 1 1 calc R U . . .
C9 C 0.40050(13) 0.33403(8) 0.2347(3) 0.0296(3) Uani 1 1 d . . . . .
C10 C 0.49342(15) 0.35725(9) 0.3421(4) 0.0358(4) Uani 1 1 d . . . . .
H10 H 0.5152 0.3379 0.4873 0.043 Uiso 1 1 calc R U . . .
C11 C 0.55396(16) 0.40752(9) 0.2419(5) 0.0416(5) Uani 1 1 d . . . . .
H11 H 0.6168 0.4225 0.3169 0.050 Uiso 1 1 calc R U . . .
C12 C 0.52177(16) 0.43602(10) 0.0301(4) 0.0412(4) Uani 1 1 d . . . . .
H12 H 0.5636 0.4700 -0.0421 0.049 Uiso 1 1 calc R U . . .
C13 C 0.42883(15) 0.41503(9) -0.0762(4) 0.0364(4) Uani 1 1 d . . . . .
H13 H 0.4072 0.4355 -0.2195 0.044 Uiso 1 1 calc R U . . .
C14 C 0.36602(13) 0.36433(8) 0.0228(3) 0.0295(3) Uani 1 1 d . . . . .
C15 C 0.26356(13) 0.34425(8) -0.0839(3) 0.0282(3) Uani 1 1 d . . . . .
C16 C 0.22221(14) 0.37811(9) -0.2810(4) 0.0334(4) Uani 1 1 d . . . . .
H16 H 0.2616 0.4137 -0.3506 0.040 Uiso 1 1 calc R U . . .
C17 C 0.12502(15) 0.36059(9) -0.3759(4) 0.0366(4) Uani 1 1 d . . . . .
H17 H 0.0987 0.3840 -0.5096 0.044 Uiso 1 1 calc R U . . .
C18 C 0.06624(14) 0.30907(10) -0.2763(4) 0.0372(4) Uani 1 1 d . . . . .
H18 H -0.0003 0.2971 -0.3413 0.045 Uiso 1 1 calc R U . . .
C19 C 0.10503(14) 0.27509(10) -0.0812(4) 0.0356(4) Uani 1 1 d . . . . .
H19 H 0.0645 0.2399 -0.0122 0.043 Uiso 1 1 calc R U . . .
C20 C 0.20339(13) 0.29208(9) 0.0154(3) 0.0296(3) Uani 1 1 d . . . . .
C21 C 0.24072(13) 0.25474(9) 0.2260(3) 0.0303(3) Uani 1 1 d . . . . .
H21 H 0.1842 0.2391 0.3363 0.036 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
C1 C6 1.396(2) . ?
C1 C2 1.400(3) . ?
C1 C7 1.487(2) . ?
C2 C3 1.395(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.383(4) . ?
C5 C6 1.392(3) . ?
C7 C21 1.524(2) . ?
C7 C8 1.529(2) . ?
C8 C9 1.475(3) . ?
C8 C21 1.507(2) . ?
C9 C10 1.403(2) . ?
C9 C14 1.414(2) . ?
C10 C11 1.380(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.400(3) . ?
C14 C15 1.486(2) . ?
C15 C20 1.403(3) . ?
C15 C16 1.406(2) . ?
C16 C17 1.387(2) . ?
C17 C18 1.385(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.401(2) . ?
C20 C21 1.484(3) . ?

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 C1 C2 118.60(17) . . ?
C6 C1 C7 119.31(17) . . ?
C2 C1 C7 122.09(16) . . ?
C3 C2 C1 120.13(19) . . ?
C4 C3 C2 120.6(2) . . ?
C3 C4 C5 119.79(19) . . ?
C4 C5 C6 120.1(2) . . ?
C5 C6 C1 120.8(2) . . ?
C1 C7 C21 119.19(15) . . ?
C1 C7 C8 119.70(15) . . ?
C21 C7 C8 59.16(11) . . ?
C9 C8 C21 118.47(16) . . ?
C9 C8 C7 119.37(15) . . ?
C21 C8 C7 60.25(11) . . ?
C10 C9 C14 119.28(17) . . ?
C10 C9 C8 119.57(17) . . ?
C14 C9 C8 121.13(15) . . ?
C11 C10 C9 121.59(19) . . ?
C10 C11 C12 119.18(18) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 121.56(19) . . ?
C13 C14 C9 118.14(16) . . ?
C13 C14 C15 121.66(16) . . ?
C9 C14 C15 120.15(16) . . ?
C20 C15 C16 118.04(15) . . ?
C20 C15 C14 120.51(15) . . ?
C16 C15 C14 121.41(16) . . ?
C17 C16 C15 121.28(18) . . ?
C18 C17 C16 120.19(18) . . ?
C17 C18 C19 119.65(17) . . ?
C18 C19 C20 120.67(19) . . ?
C19 C20 C15 120.16(17) . . ?
C19 C20 C21 118.55(17) . . ?
C15 C20 C21 121.28(15) . . ?
C20 C21 C8 118.12(16) . . ?
C20 C21 C7 120.39(16) . . ?
C8 C21 C7 60.59(10) . . ?

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
C6 C1 C2 C3 -1.2(2) . . . . ?
C7 C1 C2 C3 178.35(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C7 C1 C6 C5 -178.26(16) . . . . ?
C6 C1 C7 C21 148.17(16) . . . . ?
C2 C1 C7 C21 -31.4(2) . . . . ?
C6 C1 C7 C8 -142.77(16) . . . . ?
C2 C1 C7 C8 37.7(2) . . . . ?
C1 C7 C8 C9 143.77(15) . . . . ?
C21 C7 C8 C9 -107.97(18) . . . . ?
C1 C7 C8 C21 -108.26(17) . . . . ?
C21 C8 C9 C10 178.08(16) . . . . ?
C7 C8 C9 C10 -111.95(19) . . . . ?
C21 C8 C9 C14 -3.7(2) . . . . ?
C7 C8 C9 C14 66.3(2) . . . . ?
C14 C9 C10 C11 -2.2(3) . . . . ?
C8 C9 C10 C11 176.11(17) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C12 C13 C14 C15 176.73(17) . . . . ?
C10 C9 C14 C13 2.3(2) . . . . ?
C8 C9 C14 C13 -175.90(16) . . . . ?
C10 C9 C14 C15 -175.19(15) . . . . ?
C8 C9 C14 C15 6.6(2) . . . . ?
C13 C14 C15 C20 178.36(17) . . . . ?
C9 C14 C15 C20 -4.2(2) . . . . ?
C13 C14 C15 C16 -3.9(3) . . . . ?
C9 C14 C15 C16 173.55(16) . . . . ?
C20 C15 C16 C17 -0.2(2) . . . . ?
C14 C15 C16 C17 -178.01(17) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C18 C19 C20 C21 179.26(17) . . . . ?
C16 C15 C20 C19 -0.2(2) . . . . ?
C14 C15 C20 C19 177.66(16) . . . . ?
C16 C15 C20 C21 -178.93(15) . . . . ?
C14 C15 C20 C21 -1.1(2) . . . . ?
C19 C20 C21 C8 -174.94(16) . . . . ?
C15 C20 C21 C8 3.8(2) . . . . ?
C19 C20 C21 C7 114.45(19) . . . . ?
C15 C20 C21 C7 -66.8(2) . . . . ?
C9 C8 C21 C20 -1.5(2) . . . . ?
C7 C8 C21 C20 -110.93(18) . . . . ?
C9 C8 C21 C7 109.43(17) . . . . ?
C1 C7 C21 C20 -143.63(17) . . . . ?
C8 C7 C21 C20 107.26(19) . . . . ?
C1 C7 C21 C8 109.12(17) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.050
_shelxl_version_number           2014-3
