# 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_PD_H2L_0m
_database_code_depnum_ccdc_archive 'CCDC 1865325'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2019-01-18 downloaded from the CCDC.
;
_audit_creation_date             2018-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_formula_moiety         'C21 H20 O2'
_chemical_formula_sum            'C21 H20 O2'
_chemical_formula_weight         304.39
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
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.299(4)
_cell_length_b                   11.213(7)
_cell_length_c                   12.297(8)
_cell_angle_alpha                92.294(8)
_cell_angle_beta                 92.253(9)
_cell_angle_gamma                96.879(8)
_cell_volume                     860.7(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.42
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0569 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.9188.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.1744
_exptl_crystal_description       block
_exptl_crystal_F_000             324.1541
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10039
_diffrn_reflns_theta_full        24.8927
_diffrn_reflns_theta_max         24.89
_diffrn_reflns_theta_min         1.66
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2437
_reflns_number_total             3003
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.1714
_refine_diff_density_min         -0.1887
_refine_diff_density_rms         0.0368
_refine_ls_d_res_high            0.8443
_refine_ls_d_res_low             12.2748
_refine_ls_goodness_of_fit_ref   1.0631
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.0631
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.1392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1119
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1a), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
  C15(H15), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
;
_atom_sites_solution_primary     direct
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 0.10683(15) 0.82215(8) 0.24618(8) 0.0428(3) Uani 1.000000 .
H1 H 0.230(3) 0.8352(15) 0.2785(14) 0.0642(4) Uiso 1.000000 R
O2 O -0.48534(16) 0.89415(10) 0.34542(10) 0.0639(3) Uani 1.000000 .
C1 C 0.7047(4) 0.13010(18) 0.08109(16) 0.0773(6) Uani 1.000000 .
H1a H 0.7663(4) 0.06030(18) 0.06598(16) 0.0928(7) Uiso 1.000000 R
C2 C 0.8058(3) 0.2386(2) 0.05487(16) 0.0744(6) Uani 1.000000 .
H2 H 0.9368(3) 0.2428(2) 0.02202(16) 0.0892(7) Uiso 1.000000 R
C3 C 0.7141(3) 0.34310(16) 0.07695(14) 0.0587(4) Uani 1.000000 .
H3 H 0.7848(3) 0.41683(16) 0.05897(14) 0.0705(5) Uiso 1.000000 R
C4 C 0.5183(2) 0.33891(13) 0.12549(11) 0.0461(4) Uani 1.000000 .
C5 C 0.4258(2) 0.45137(13) 0.14648(13) 0.0488(4) Uani 1.000000 .
H5 H 0.4927(2) 0.51918(13) 0.11503(13) 0.0586(5) Uiso 1.000000 R
C6 C 0.2576(2) 0.46789(13) 0.20512(12) 0.0493(4) Uani 1.000000 .
H6 H 0.1839(2) 0.40142(13) 0.23563(12) 0.0592(5) Uiso 1.000000 R
C7 C 0.1832(2) 0.58465(13) 0.22389(12) 0.0459(4) Uani 1.000000 .
H7 H 0.2508(2) 0.64826(13) 0.18693(12) 0.0550(4) Uiso 1.000000 R
C8 C 0.0281(2) 0.60971(12) 0.28864(11) 0.0401(3) Uani 1.000000 .
C9 C -0.0255(2) 0.73760(11) 0.30543(11) 0.0368(3) Uani 1.000000 .
C10 C -0.0144(2) 0.77960(11) 0.42573(11) 0.0383(3) Uani 1.000000 .
C11 C -0.1847(2) 0.84115(12) 0.45133(12) 0.0416(3) Uani 1.000000 .
C12 C -0.1993(3) 0.89534(14) 0.55447(13) 0.0542(4) Uani 1.000000 .
H12 H -0.3143(3) 0.93673(14) 0.57076(13) 0.0650(5) Uiso 1.000000 R
C13 C -0.0382(3) 0.88565(15) 0.63134(13) 0.0591(4) Uani 1.000000 .
H13 H -0.0432(3) 0.92160(15) 0.70052(13) 0.0709(5) Uiso 1.000000 R
C14 C 0.1310(3) 0.82294(14) 0.60660(12) 0.0576(4) Uani 1.000000 .
H14 H 0.2373(3) 0.81643(14) 0.65996(12) 0.0692(5) Uiso 1.000000 R
C15 C 0.1457(2) 0.76952(13) 0.50391(12) 0.0489(4) Uani 1.000000 .
H15 H 0.2606(2) 0.72788(13) 0.48798(12) 0.0587(5) Uiso 1.000000 R
C16 C -0.3310(2) 0.83853(12) 0.35503(12) 0.0439(4) Uani 1.000000 .
C17 C -0.2603(2) 0.75216(12) 0.26936(11) 0.0405(3) Uani 1.000000 .
H17 H -0.3457(2) 0.67418(12) 0.27704(11) 0.0487(4) Uiso 1.000000 R
C18 C -0.2949(3) 0.78649(16) 0.15277(13) 0.0565(4) Uani 1.000000 .
H18a H -0.4427(4) 0.7965(10) 0.1393(3) 0.0848(6) Uiso 1.000000 GR
H18b H -0.2073(14) 0.8606(5) 0.1409(3) 0.0848(6) Uiso 1.000000 GR
H18c H -0.2565(17) 0.7242(5) 0.10414(13) 0.0848(6) Uiso 1.000000 GR
C19 C -0.1009(3) 0.51566(13) 0.35085(13) 0.0542(4) Uani 1.000000 .
H19a H -0.2051(12) 0.4693(7) 0.3022(2) 0.0812(6) Uiso 1.000000 GR
H19b H -0.0074(4) 0.4636(6) 0.3825(8) 0.0812(6) Uiso 1.000000 GR
H19c H -0.1724(14) 0.55410(14) 0.4075(6) 0.0812(6) Uiso 1.000000 GR
C20 C 0.4192(3) 0.22731(14) 0.15115(14) 0.0584(4) Uani 1.000000 .
H20 H 0.2875(3) 0.22185(14) 0.18342(14) 0.0701(5) Uiso 1.000000 R
C21 C 0.5123(4) 0.12381(16) 0.12972(15) 0.0720(5) Uani 1.000000 .
H21 H 0.4439(4) 0.04975(16) 0.14839(15) 0.0864(6) 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 H1 0.852(18) . ?
O1 C9 1.4277(17) . ?
O2 C16 1.2208(17) . ?
C1 H1a 0.9300 . ?
C1 C2 1.361(3) . ?
C1 C21 1.368(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 C5 1.469(2) . ?
C4 C20 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.332(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.455(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.333(2) . ?
C8 C9 1.520(2) . ?
C8 C19 1.505(2) . ?
C9 C10 1.531(2) . ?
C9 C17 1.557(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.383(2) . ?
C11 C12 1.395(2) . ?
C11 C16 1.469(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.518(2) . ?
C17 H17 0.9800 . ?
C17 C18 1.514(2) . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
C19 H19a 0.9600 . ?
C19 H19b 0.9600 . ?
C19 H19c 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.382(2) . ?
C21 H21 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
C9 O1 H1 108.8(12) . . ?
C2 C1 H1a 120.04(11) . . ?
C21 C1 H1a 120.04(11) . . ?
C21 C1 C2 119.92(17) . . ?
H2 C2 C1 119.86(11) . . ?
C3 C2 C1 120.28(19) . . ?
C3 C2 H2 119.86(12) . . ?
H3 C3 C2 119.57(12) . . ?
C4 C3 C2 120.85(18) . . ?
C4 C3 H3 119.57(10) . . ?
C5 C4 C3 119.15(15) . . ?
C20 C4 C3 117.58(15) . . ?
C20 C4 C5 123.27(15) . . ?
H5 C5 C4 116.10(9) . . ?
C6 C5 C4 127.80(15) . . ?
C6 C5 H5 116.10(10) . . ?
H6 C6 C5 118.33(9) . . ?
C7 C6 C5 123.34(15) . . ?
C7 C6 H6 118.33(9) . . ?
H7 C7 C6 116.68(9) . . ?
C8 C7 C6 126.64(15) . . ?
C8 C7 H7 116.68(9) . . ?
C9 C8 C7 121.12(13) . . ?
C19 C8 C7 122.92(13) . . ?
C19 C8 C9 115.95(12) . . ?
C8 C9 O1 112.77(11) . . ?
C10 C9 O1 109.15(10) . . ?
C10 C9 C8 112.60(11) . . ?
C17 C9 O1 105.92(10) . . ?
C17 C9 C8 113.22(10) . . ?
C17 C9 C10 102.48(10) . . ?
C11 C10 C9 111.76(11) . . ?
C15 C10 C9 128.26(13) . . ?
C15 C10 C11 119.84(13) . . ?
C12 C11 C10 121.72(14) . . ?
C16 C11 C10 109.03(12) . . ?
C16 C11 C12 129.25(13) . . ?
H12 C12 C11 121.02(9) . . ?
C13 C12 C11 117.95(15) . . ?
C13 C12 H12 121.02(10) . . ?
H13 C13 C12 119.72(10) . . ?
C14 C13 C12 120.56(14) . . ?
C14 C13 H13 119.72(9) . . ?
H14 C14 C13 119.29(9) . . ?
C15 C14 C13 121.43(15) . . ?
C15 C14 H14 119.29(10) . . ?
C14 C15 C10 118.50(15) . . ?
H15 C15 C10 120.75(9) . . ?
H15 C15 C14 120.75(10) . . ?
C11 C16 O2 126.35(14) . . ?
C17 C16 O2 125.45(13) . . ?
C17 C16 C11 108.18(11) . . ?
C16 C17 C9 104.54(10) . . ?
H17 C17 C9 107.01(7) . . ?
H17 C17 C16 107.01(7) . . ?
C18 C17 C9 115.71(12) . . ?
C18 C17 C16 115.01(12) . . ?
C18 C17 H17 107.01(8) . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 C8 109.5 . . ?
H19b C19 C8 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C8 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H20 C20 C4 119.38(10) . . ?
C21 C20 C4 121.24(18) . . ?
C21 C20 H20 119.38(12) . . ?
C20 C21 C1 120.12(19) . . ?
H21 C21 C1 119.94(11) . . ?
H21 C21 C20 119.94(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.852(18) 1.970(19) 2.814(2) 170.0(16) 1_655

_olex2_submission_special_instructions 'No special instructions were received'
