# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

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

data_RH_mono_S
_database_code_depnum_ccdc_archive 'CCDC 2226943'
loop_
_audit_author_name
_audit_author_address
'Vaclav Eigner'
;Institute of Physics AS CR, v v i  Czech Republic
Czech Republic
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

_cell_length_a                   9.03801(13)
_cell_length_b                   6.43800(9)
_cell_length_c                   13.58790(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.0399(12)
_cell_angle_gamma                90
_cell_volume                     790.635(19)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C21 H14 N2 O'
_chemical_formula_moiety         'C21 H14 N2 O'
_chemical_compound_source        .
_chemical_formula_weight         310.35


_cell_measurement_reflns_used    7380
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      67.56
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.084
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_max          0.218

_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             323.999
_exptl_absorpt_coefficient_mu    0.644

_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.95
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      180
_diffrn_ambient_pressure         101
_diffrn_reflns_number            11296
_diffrn_reflns_av_unetI/netI     0.044
_reflns_number_total             2832
_diffrn_reflns_av_R_equivalents  0.030

_diffrn_reflns_theta_min         3.252
_diffrn_reflns_theta_max         67.577
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        67.577
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -7
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.11

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     9
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2832
_oxford_refine_ls_R_factor_ref   0.0294
_refine_ls_R_factor_all          0.0294
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_all         0.0782
_refine_ls_goodness_of_fit_ref   0.9855
_refine_ls_shift/su_max          0.0004041
_refine_ls_shift/su_mean         0.0000367

_oxford_reflns_number_all        2832
_oxford_refine_ls_R_factor_all   0.0294
_oxford_refine_ls_wR_factor_all  0.0782

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2722
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_gt          0.0733

_oxford_Hooft_y                  0.07(12) # for 1175 Friedel pairs 
_oxford_Bijvoet_difference       0.11(13) # for 1175 Friedel pairs 
_oxford_refined_Flack_x          0.2(3) # for 1273 Friedel pairs 
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1175 Friedel Pairs 
;

_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.12P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.48747(11) 0.49989(19) 0.49191(7) 0.0349 1.0000 Uani . . . . . .
C2 C 0.39409(14) 0.5002(3) 0.55845(9) 0.0287 1.0000 Uani D . . . . .
N3 N 0.34813(14) 0.6829(2) 0.59892(9) 0.0315 1.0000 Uani D . . . . .
C4 C 0.31656(15) 0.7038(2) 0.70078(10) 0.0297 1.0000 Uani D . . . . .
C5 C 0.21927(15) 0.5732(2) 0.74715(10) 0.0287 1.0000 Uani . . . . . .
C6 C 0.12412(15) 0.4300(2) 0.68941(10) 0.0278 1.0000 Uani . . . . . .
C7 C -0.03352(16) 0.4266(3) 0.70316(10) 0.0309 1.0000 Uani . . . . . .
C8 C -0.11862(17) 0.2673(3) 0.65862(11) 0.0354 1.0000 Uani . . . . . .
C9 C -0.04695(19) 0.1211(3) 0.59747(12) 0.0403 1.0000 Uani . . . . . .
C10 C 0.09968(18) 0.1393(3) 0.57580(11) 0.0356 1.0000 Uani . . . . . .
C11 C 0.18440(16) 0.2980(2) 0.62076(10) 0.0298 1.0000 Uani D . . . . .
N12 N 0.33479(14) 0.3186(2) 0.59143(9) 0.0307 1.0000 Uani D . . . . .
C13 C -0.27336(17) 0.2629(3) 0.67539(12) 0.0435 1.0000 Uani . . . . . .
C14 C -0.34118(17) 0.4109(3) 0.73060(12) 0.0458 1.0000 Uani . . . . . .
C15 C -0.25852(18) 0.5742(3) 0.77074(12) 0.0438 1.0000 Uani . . . . . .
C16 C -0.10827(16) 0.5825(3) 0.75755(11) 0.0362 1.0000 Uani . . . . . .
C17 C 0.21215(15) 0.5775(3) 0.85282(11) 0.0311 1.0000 Uani . . . . . .
C18 C 0.13420(17) 0.4258(3) 0.90784(11) 0.0385 1.0000 Uani . . . . . .
C19 C 0.1303(2) 0.4336(3) 1.00881(12) 0.0481 1.0000 Uani . . . . . .
C20 C 0.2041(2) 0.5914(3) 1.05986(13) 0.0517 1.0000 Uani . . . . . .
C21 C 0.28252(19) 0.7378(3) 1.00942(13) 0.0475 1.0000 Uani . . . . . .
C22 C 0.29025(17) 0.7342(3) 0.90549(12) 0.0374 1.0000 Uani . . . . . .
C23 C 0.37631(18) 0.8796(3) 0.85194(13) 0.0419 1.0000 Uani . . . . . .
C24 C 0.39213(17) 0.8623(3) 0.75317(12) 0.0370 1.0000 Uani . . . . . .
H91 H -0.1018 0.0115 0.5718 0.0493 1.0000 Uiso R . . . . .
H101 H 0.1498 0.0459 0.5327 0.0427 1.0000 Uiso R . . . . .
H131 H -0.3286 0.1536 0.6452 0.0522 1.0000 Uiso R . . . . .
H141 H -0.4488 0.4024 0.7412 0.0551 1.0000 Uiso R . . . . .
H151 H -0.3102 0.6798 0.8070 0.0524 1.0000 Uiso R . . . . .
H161 H -0.0529 0.6947 0.7852 0.0440 1.0000 Uiso R . . . . .
H181 H 0.0877 0.3132 0.8749 0.0467 1.0000 Uiso R . . . . .
H191 H 0.0758 0.3300 1.0436 0.0557 1.0000 Uiso R . . . . .
H201 H 0.1980 0.5994 1.1296 0.0615 1.0000 Uiso R . . . . .
H211 H 0.3342 0.8452 1.0454 0.0588 1.0000 Uiso R . . . . .
H231 H 0.4215 0.9886 0.8869 0.0512 1.0000 Uiso R . . . . .
H241 H 0.4538 0.9563 0.7146 0.0435 1.0000 Uiso R . . . . .
H31 H 0.3975(18) 0.789(2) 0.5732(11) 0.0388(18) 1.0000 Uiso D . . . . .
H121 H 0.3723(17) 0.210(2) 0.5584(12) 0.0376(18) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          12.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2372(16) yes
C2 . N3 . 1.363(2) yes
C2 . N12 . 1.362(2) yes
N3 . C4 . 1.4197(19) yes
N3 . H31 . 0.889(15) no
C4 . C5 . 1.370(2) yes
C4 . C24 . 1.419(2) yes
C5 . C6 . 1.4848(19) yes
C5 . C17 . 1.438(2) yes
C6 . C7 . 1.4372(19) yes
C6 . C11 . 1.375(2) yes
C7 . C8 . 1.417(2) yes
C7 . C16 . 1.418(2) yes
C8 . C9 . 1.413(2) yes
C8 . C13 . 1.417(2) yes
C9 . C10 . 1.363(2) yes
C9 . H91 . 0.930 no
C10 . C11 . 1.415(2) yes
C10 . H101 . 0.955 no
C11 . N12 . 1.4229(19) yes
N12 . H121 . 0.898(14) no
C13 . C14 . 1.359(3) yes
C13 . H131 . 0.956 no
C14 . C15 . 1.400(3) yes
C14 . H141 . 0.985 no
C15 . C16 . 1.371(2) yes
C15 . H151 . 0.961 no
C16 . H161 . 0.955 no
C17 . C18 . 1.418(2) yes
C17 . C22 . 1.424(2) yes
C18 . C19 . 1.373(2) yes
C18 . H181 . 0.950 no
C19 . C20 . 1.399(3) yes
C19 . H191 . 0.955 no
C20 . C21 . 1.364(3) yes
C20 . H201 . 0.951 no
C21 . C22 . 1.414(2) yes
C21 . H211 . 0.967 no
C22 . C23 . 1.418(2) yes
C23 . C24 . 1.354(2) yes
C23 . H231 . 0.941 no
C24 . H241 . 0.976 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 120.28(14) yes
O1 . C2 . N12 . 120.54(14) yes
N3 . C2 . N12 . 119.18(11) yes
C2 . N3 . C4 . 122.44(12) yes
C2 . N3 . H31 . 110.6(10) no
C4 . N3 . H31 . 114.3(10) no
N3 . C4 . C5 . 121.31(13) yes
N3 . C4 . C24 . 117.40(13) yes
C5 . C4 . C24 . 121.28(13) yes
C4 . C5 . C6 . 120.64(12) yes
C4 . C5 . C17 . 118.48(13) yes
C6 . C5 . C17 . 120.88(13) yes
C5 . C6 . C7 . 120.97(13) yes
C5 . C6 . C11 . 120.85(12) yes
C7 . C6 . C11 . 118.18(13) yes
C6 . C7 . C8 . 119.55(14) yes
C6 . C7 . C16 . 121.99(14) yes
C8 . C7 . C16 . 118.43(13) yes
C7 . C8 . C9 . 118.96(13) yes
C7 . C8 . C13 . 118.75(15) yes
C9 . C8 . C13 . 122.28(15) yes
C8 . C9 . C10 . 121.05(14) yes
C8 . C9 . H91 . 118.8 no
C10 . C9 . H91 . 120.2 no
C9 . C10 . C11 . 119.66(14) yes
C9 . C10 . H101 . 122.7 no
C11 . C10 . H101 . 117.6 no
C10 . C11 . C6 . 121.64(13) yes
C10 . C11 . N12 . 117.59(13) yes
C6 . C11 . N12 . 120.76(13) yes
C11 . N12 . C2 . 123.27(12) yes
C11 . N12 . H121 . 115.3(10) no
C2 . N12 . H121 . 110.9(9) no
C8 . C13 . C14 . 121.35(16) yes
C8 . C13 . H131 . 117.5 no
C14 . C13 . H131 . 121.2 no
C13 . C14 . C15 . 120.05(15) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 120.8 no
C14 . C15 . C16 . 120.43(17) yes
C14 . C15 . H151 . 118.1 no
C16 . C15 . H151 . 121.4 no
C7 . C16 . C15 . 120.86(16) yes
C7 . C16 . H161 . 119.4 no
C15 . C16 . H161 . 119.8 no
C5 . C17 . C18 . 122.42(14) yes
C5 . C17 . C22 . 119.53(14) yes
C18 . C17 . C22 . 118.00(13) yes
C17 . C18 . C19 . 120.97(15) yes
C17 . C18 . H181 . 119.8 no
C19 . C18 . H181 . 119.2 no
C18 . C19 . C20 . 120.63(17) yes
C18 . C19 . H191 . 118.8 no
C20 . C19 . H191 . 120.5 no
C19 . C20 . C21 . 120.01(16) yes
C19 . C20 . H201 . 120.4 no
C21 . C20 . H201 . 119.6 no
C20 . C21 . C22 . 121.11(16) yes
C20 . C21 . H211 . 119.4 no
C22 . C21 . H211 . 119.5 no
C17 . C22 . C21 . 119.24(15) yes
C17 . C22 . C23 . 118.79(14) yes
C21 . C22 . C23 . 121.95(15) yes
C22 . C23 . C24 . 120.84(14) yes
C22 . C23 . H231 . 118.1 no
C24 . C23 . H231 . 121.0 no
C4 . C24 . C23 . 120.33(14) yes
C4 . C24 . H241 . 116.8 no
C23 . C24 . H241 . 122.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O1 2_546 153 0.96 2.55 3.431(2) yes
N3 . H31 . O1 2_656 174.2(14) 0.889(15) 1.924(15) 2.810(2) yes
N12 . H121 . O1 2_646 161.6(15) 0.898(14) 1.976(15) 2.842(2) yes


####################################################################### 
# 
# 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_CyklDimer2
_database_code_depnum_ccdc_archive 'CCDC 2226944'
loop_
_audit_author_name
_audit_author_address
'Vaclav Eigner'
;Institute of Physics AS CR, v v i  Czech Republic
Czech Republic
;
_audit_update_record             
;
2022-12-16 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

_cell_length_a                   9.8861(6)
_cell_length_b                   15.6415(10)
_cell_length_c                   10.3461(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.9826(19)
_cell_angle_gamma                90
_cell_volume                     1538.01(17)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C42 H28 N4 O2'
_chemical_formula_moiety         'C42 H28 N4 O2'
_chemical_compound_source        .
_chemical_formula_weight         620.71


_cell_measurement_reflns_used    123
_cell_measurement_theta_min      11.54
_cell_measurement_theta_max      55.70
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.284
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_max          0.452

_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             647.997
_exptl_absorpt_coefficient_mu    0.662

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.83
_diffrn_measurement_device_type  'Bruker Kappa Apex3'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

_computing_data_collection       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      180
_diffrn_ambient_pressure         101
_diffrn_reflns_number            22298
_reflns_number_total             5623
_diffrn_reflns_av_R_equivalents  0.041


_diffrn_reflns_theta_min         4.445
_diffrn_reflns_theta_max         68.294
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        68.294
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -18
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.22
_oxford_diffrn_Wilson_scale      13.60

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.16


_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     17
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5621
_oxford_refine_ls_R_factor_ref   0.0311
_refine_ls_R_factor_all          0.0311
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_all         0.0854
_refine_ls_goodness_of_fit_ref   1.0004
_refine_ls_shift/su_max          0.0003686
_refine_ls_shift/su_mean         0.0000442

_oxford_reflns_number_all        5621
_oxford_refine_ls_R_factor_all   0.0311
_oxford_refine_ls_wR_factor_all  0.0854

_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5544
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_gt          0.0849

_oxford_Hooft_y                  0.02(7) # for 2131 Friedel pairs 
_oxford_Bijvoet_difference       0.00(7) # for 2131 Friedel pairs 
_oxford_refined_Flack_x          -0.03(18) # for 2689 Friedel pairs 
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 2131 Friedel Pairs 
;

_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.21P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.23155(14) 0.39519(10) 0.67629(14) 0.0248 1.0000 Uani . . . . . .
C2 C 0.21285(15) 0.45422(10) 0.57263(14) 0.0289 1.0000 Uani D . . . . .
C3 C 0.2721(2) 0.43964(12) 0.46408(17) 0.0408 1.0000 Uani . . . . . .
C4 C 0.35051(19) 0.36820(13) 0.46336(17) 0.0442 1.0000 Uani . . . . . .
C5 C 0.46586(18) 0.23590(11) 0.57171(18) 0.0403 1.0000 Uani . . . . . .
C6 C 0.49619(17) 0.18086(11) 0.67752(19) 0.0414 1.0000 Uani . . . . . .
C7 C 0.43552(17) 0.19362(11) 0.78477(18) 0.0380 1.0000 Uani . . . . . .
C8 C 0.34648(16) 0.26117(10) 0.78337(16) 0.0319 1.0000 Uani . . . . . .
C9 C 0.31597(14) 0.32115(10) 0.67692(15) 0.0270 1.0000 Uani . . . . . .
C10 C 0.37659(16) 0.30751(11) 0.56806(16) 0.0335 1.0000 Uani . . . . . .
C11 C 0.16734(14) 0.41077(9) 0.78961(14) 0.0233 1.0000 Uani . . . . . .
C12 C 0.25081(14) 0.43849(9) 0.91270(14) 0.0236 1.0000 Uani D . . . . .
C13 C 0.19291(15) 0.45488(10) 1.02121(14) 0.0273 1.0000 Uani . . . . . .
C14 C 0.05251(16) 0.44492(10) 1.00513(15) 0.0293 1.0000 Uani . . . . . .
C15 C -0.18600(16) 0.41422(11) 0.85891(18) 0.0357 1.0000 Uani . . . . . .
C16 C -0.27279(16) 0.39306(12) 0.73632(19) 0.0408 1.0000 Uani . . . . . .
C17 C -0.21627(17) 0.37406(11) 0.62919(17) 0.0386 1.0000 Uani . . . . . .
C18 C -0.07423(15) 0.37727(10) 0.64566(15) 0.0304 1.0000 Uani . . . . . .
C19 C 0.01951(14) 0.40079(9) 0.77101(14) 0.0245 1.0000 Uani . . . . . .
C20 C -0.03847(15) 0.41899(9) 0.88045(15) 0.0265 1.0000 Uani . . . . . .
C21 C 0.09605(14) 0.69089(9) 0.78977(14) 0.0245 1.0000 Uani . . . . . .
C22 C 0.00841(14) 0.66417(10) 0.66814(14) 0.0267 1.0000 Uani D . . . . .
C23 C -0.12668(15) 0.63074(11) 0.65880(16) 0.0324 1.0000 Uani . . . . . .
C24 C -0.17269(14) 0.62280(10) 0.77179(16) 0.0331 1.0000 Uani . . . . . .
C25 C -0.12671(15) 0.63604(10) 1.01962(17) 0.0338 1.0000 Uani . . . . . .
C26 C -0.03812(17) 0.65812(10) 1.14174(16) 0.0350 1.0000 Uani . . . . . .
C27 C 0.09586(17) 0.69210(11) 1.15110(16) 0.0330 1.0000 Uani . . . . . .
C28 C 0.13927(14) 0.70403(9) 1.03770(15) 0.0282 1.0000 Uani . . . . . .
C29 C 0.05072(14) 0.68203(9) 0.90922(14) 0.0244 1.0000 Uani . . . . . .
C30 C -0.08490(14) 0.64679(9) 0.89939(16) 0.0280 1.0000 Uani . . . . . .
C31 C 0.23573(14) 0.73016(9) 0.79813(13) 0.0242 1.0000 Uani . . . . . .
C32 C 0.35866(14) 0.68299(10) 0.83821(14) 0.0265 1.0000 Uani D . . . . .
C33 C 0.49054(15) 0.72180(10) 0.84788(15) 0.0294 1.0000 Uani . . . . . .
C34 C 0.49664(15) 0.80649(11) 0.81801(14) 0.0303 1.0000 Uani . . . . . .
C35 C 0.37876(18) 0.94585(11) 0.74612(16) 0.0359 1.0000 Uani . . . . . .
C36 C 0.25884(19) 0.99366(10) 0.70979(17) 0.0389 1.0000 Uani . . . . . .
C37 C 0.12786(18) 0.95571(11) 0.70205(15) 0.0356 1.0000 Uani . . . . . .
C38 C 0.11920(16) 0.87070(10) 0.72969(14) 0.0296 1.0000 Uani . . . . . .
C39 C 0.24159(15) 0.81892(10) 0.76695(13) 0.0257 1.0000 Uani . . . . . .
C40 C 0.37478(15) 0.85752(10) 0.77704(13) 0.0280 1.0000 Uani . . . . . .
N41 N 0.13169(14) 0.52759(9) 0.57620(13) 0.0304 1.0000 Uani D . . . . .
C42 C 0.14341(16) 0.60560(11) 0.52025(14) 0.0320 1.0000 Uani D . . . . .
N43 N 0.05632(14) 0.66775(9) 0.54896(13) 0.0324 1.0000 Uani D . . . . .
O44 O 0.21891(15) 0.62019(9) 0.44782(14) 0.0517 1.0000 Uani . . . . . .
N45 N 0.39615(12) 0.45644(8) 0.93065(12) 0.0272 1.0000 Uani D . . . . .
C46 C 0.44563(14) 0.53410(10) 0.90088(15) 0.0269 1.0000 Uani D . . . . .
O47 O 0.56788(11) 0.54389(8) 0.90256(15) 0.0480 1.0000 Uani . . . . . .
N48 N 0.34625(12) 0.59722(8) 0.87399(14) 0.0303 1.0000 Uani D . . . . .
H331 H 0.5723 0.6914 0.8760 0.0293 1.0000 Uiso R . . . . .
H341 H 0.5844 0.8300 0.8237 0.0297 1.0000 Uiso R . . . . .
H381 H 0.0315 0.8436 0.7255 0.0277 1.0000 Uiso R . . . . .
H371 H 0.0452 0.9914 0.6755 0.0369 1.0000 Uiso R . . . . .
H361 H 0.2615 1.0514 0.6865 0.0424 1.0000 Uiso R . . . . .
H351 H 0.4681 0.9720 0.7517 0.0380 1.0000 Uiso R . . . . .
H281 H 0.2295 0.7297 1.0450 0.0277 1.0000 Uiso R . . . . .
H271 H 0.1565 0.7098 1.2374 0.0336 1.0000 Uiso R . . . . .
H261 H -0.0665 0.6495 1.2200 0.0374 1.0000 Uiso R . . . . .
H251 H -0.2158 0.6092 1.0139 0.0346 1.0000 Uiso R . . . . .
H241 H -0.2624 0.5983 0.7648 0.0329 1.0000 Uiso R . . . . .
H231 H -0.1845 0.6098 0.5735 0.0330 1.0000 Uiso R . . . . .
H31 H 0.2549 0.4809 0.3920 0.0411 1.0000 Uiso R . . . . .
H41 H 0.3878 0.3553 0.3907 0.0441 1.0000 Uiso R . . . . .
H81 H 0.3062 0.2701 0.8535 0.0324 1.0000 Uiso R . . . . .
H71 H 0.4561 0.1545 0.8586 0.0380 1.0000 Uiso R . . . . .
H61 H 0.5590 0.1333 0.6835 0.0452 1.0000 Uiso R . . . . .
H51 H 0.5035 0.2287 0.4983 0.0403 1.0000 Uiso R . . . . .
H141 H 0.0147 0.4602 1.0753 0.0282 1.0000 Uiso R . . . . .
H131 H 0.2536 0.4767 1.1052 0.0271 1.0000 Uiso R . . . . .
H151 H -0.2238 0.4280 0.9317 0.0354 1.0000 Uiso R . . . . .
H161 H -0.3725 0.3895 0.7226 0.0435 1.0000 Uiso R . . . . .
H171 H -0.2754 0.3548 0.5449 0.0402 1.0000 Uiso R . . . . .
H181 H -0.0366 0.3597 0.5744 0.0336 1.0000 Uiso R . . . . .
H411 H 0.0717(19) 0.5236(10) 0.6230(18) 0.0400(18) 1.0000 Uiso D . . . . .
H481 H 0.2596(16) 0.5813(9) 0.8698(19) 0.0352(18) 1.0000 Uiso D . . . . .
H451 H 0.4542(15) 0.4147(10) 0.9435(18) 0.0352(18) 1.0000 Uiso D . . . . .
H431 H 0.0736(18) 0.7187(10) 0.5221(17) 0.0411(19) 1.0000 Uiso D . . . . .

_refine_ls_extinction_coef       250(10)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.2867(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.388(2) yes
C1 . C9 . 1.426(2) yes
C1 . C11 . 1.4989(17) yes
C2 . C3 . 1.4209(19) yes
C2 . N41 . 1.407(2) yes
C3 . C4 . 1.361(3) yes
C3 . H31 . 0.966 no
C4 . C10 . 1.410(3) yes
C4 . H41 . 0.945 no
C5 . C6 . 1.360(3) yes
C5 . C10 . 1.420(2) yes
C5 . H51 . 0.940 no
C6 . C7 . 1.413(2) yes
C6 . H61 . 0.960 no
C7 . C8 . 1.373(2) yes
C7 . H71 . 0.956 no
C8 . C9 . 1.415(2) yes
C8 . H81 . 0.930 no
C9 . C10 . 1.4300(19) yes
C11 . C12 . 1.383(2) yes
C11 . C19 . 1.4291(18) yes
C12 . C13 . 1.4169(18) yes
C12 . N45 . 1.4250(17) yes
C13 . C14 . 1.361(2) yes
C13 . H131 . 0.972 no
C14 . C20 . 1.414(2) yes
C14 . H141 . 0.935 no
C15 . C16 . 1.362(3) yes
C15 . C20 . 1.4155(19) yes
C15 . H151 . 0.952 no
C16 . C17 . 1.404(2) yes
C16 . H161 . 0.958 no
C17 . C18 . 1.368(2) yes
C17 . H171 . 0.956 no
C18 . C19 . 1.419(2) yes
C18 . H181 . 0.953 no
C19 . C20 . 1.4314(18) yes
C21 . C22 . 1.381(2) yes
C21 . C29 . 1.4326(18) yes
C21 . C31 . 1.4919(18) yes
C22 . C23 . 1.413(2) yes
C22 . N43 . 1.4385(18) yes
C23 . C24 . 1.372(2) yes
C23 . H231 . 0.968 no
C24 . C30 . 1.416(2) yes
C24 . H241 . 0.951 no
C25 . C26 . 1.369(2) yes
C25 . C30 . 1.425(2) yes
C25 . H251 . 0.962 no
C26 . C27 . 1.406(2) yes
C26 . H261 . 0.937 no
C27 . C28 . 1.369(2) yes
C27 . H271 . 0.968 no
C28 . C29 . 1.418(2) yes
C28 . H281 . 0.962 no
C29 . C30 . 1.4271(18) yes
C31 . C32 . 1.384(2) yes
C31 . C39 . 1.4300(19) yes
C32 . C33 . 1.4166(19) yes
C32 . N48 . 1.4059(19) yes
C33 . C34 . 1.365(2) yes
C33 . H331 . 0.913 no
C34 . C40 . 1.410(2) yes
C34 . H341 . 0.929 no
C35 . C36 . 1.364(3) yes
C35 . C40 . 1.421(2) yes
C35 . H351 . 0.961 no
C36 . C37 . 1.407(2) yes
C36 . H361 . 0.937 no
C37 . C38 . 1.368(2) yes
C37 . H371 . 0.965 no
C38 . C39 . 1.418(2) yes
C38 . H381 . 0.955 no
C39 . C40 . 1.4261(19) yes
N41 . C42 . 1.369(2) yes
N41 . H411 . 0.865(15) no
C42 . N43 . 1.384(2) yes
C42 . O44 . 1.2161(19) yes
N43 . H431 . 0.876(15) no
N45 . C46 . 1.3758(19) yes
N45 . H451 . 0.856(14) no
C46 . O47 . 1.2136(17) yes
C46 . N48 . 1.3664(19) yes
N48 . H481 . 0.882(14) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C9 . 119.78(12) yes
C2 . C1 . C11 . 120.07(12) yes
C9 . C1 . C11 . 120.12(12) yes
C1 . C2 . C3 . 120.51(14) yes
C1 . C2 . N41 . 118.55(12) yes
C3 . C2 . N41 . 120.93(13) yes
C2 . C3 . C4 . 119.70(15) yes
C2 . C3 . H31 . 118.7 no
C4 . C3 . H31 . 121.6 no
C3 . C4 . C10 . 122.18(13) yes
C3 . C4 . H41 . 121.8 no
C10 . C4 . H41 . 116.0 no
C6 . C5 . C10 . 121.23(14) yes
C6 . C5 . H51 . 121.7 no
C10 . C5 . H51 . 117.1 no
C5 . C6 . C7 . 119.70(15) yes
C5 . C6 . H61 . 122.5 no
C7 . C6 . H61 . 117.8 no
C6 . C7 . C8 . 120.66(15) yes
C6 . C7 . H71 . 119.6 no
C8 . C7 . H71 . 119.7 no
C7 . C8 . C9 . 121.15(14) yes
C7 . C8 . H81 . 121.3 no
C9 . C8 . H81 . 117.5 no
C1 . C9 . C8 . 122.76(12) yes
C1 . C9 . C10 . 119.28(13) yes
C8 . C9 . C10 . 117.93(13) yes
C9 . C10 . C5 . 119.27(15) yes
C9 . C10 . C4 . 118.50(14) yes
C5 . C10 . C4 . 122.17(14) yes
C1 . C11 . C12 . 119.83(11) yes
C1 . C11 . C19 . 120.97(12) yes
C12 . C11 . C19 . 119.15(11) yes
C11 . C12 . C13 . 121.17(12) yes
C11 . C12 . N45 . 120.42(11) yes
C13 . C12 . N45 . 118.29(12) yes
C12 . C13 . C14 . 120.23(13) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 120.5 no
C13 . C14 . C20 . 121.04(12) yes
C13 . C14 . H141 . 119.2 no
C20 . C14 . H141 . 119.5 no
C16 . C15 . C20 . 121.13(14) yes
C16 . C15 . H151 . 120.5 no
C20 . C15 . H151 . 118.3 no
C15 . C16 . C17 . 120.07(14) yes
C15 . C16 . H161 . 120.7 no
C17 . C16 . H161 . 119.2 no
C16 . C17 . C18 . 120.80(15) yes
C16 . C17 . H171 . 120.7 no
C18 . C17 . H171 . 118.3 no
C17 . C18 . C19 . 120.85(14) yes
C17 . C18 . H181 . 119.9 no
C19 . C18 . H181 . 119.1 no
C11 . C19 . C18 . 122.52(12) yes
C11 . C19 . C20 . 119.28(12) yes
C18 . C19 . C20 . 118.13(12) yes
C19 . C20 . C15 . 118.99(13) yes
C19 . C20 . C14 . 119.09(12) yes
C15 . C20 . C14 . 121.86(13) yes
C22 . C21 . C29 . 119.33(12) yes
C22 . C21 . C31 . 121.04(12) yes
C29 . C21 . C31 . 119.62(12) yes
C21 . C22 . C23 . 121.22(13) yes
C21 . C22 . N43 . 119.80(12) yes
C23 . C22 . N43 . 118.95(12) yes
C22 . C23 . C24 . 120.29(13) yes
C22 . C23 . H231 . 119.9 no
C24 . C23 . H231 . 119.7 no
C23 . C24 . C30 . 120.56(13) yes
C23 . C24 . H241 . 119.6 no
C30 . C24 . H241 . 119.8 no
C26 . C25 . C30 . 120.70(13) yes
C26 . C25 . H251 . 120.6 no
C30 . C25 . H251 . 118.6 no
C25 . C26 . C27 . 120.68(13) yes
C25 . C26 . H261 . 119.6 no
C27 . C26 . H261 . 119.7 no
C26 . C27 . C28 . 120.30(14) yes
C26 . C27 . H271 . 120.3 no
C28 . C27 . H271 . 119.4 no
C27 . C28 . C29 . 120.81(12) yes
C27 . C28 . H281 . 119.5 no
C29 . C28 . H281 . 119.6 no
C21 . C29 . C28 . 121.75(12) yes
C21 . C29 . C30 . 119.13(12) yes
C28 . C29 . C30 . 119.07(12) yes
C29 . C30 . C25 . 118.43(13) yes
C29 . C30 . C24 . 119.43(13) yes
C25 . C30 . C24 . 122.13(13) yes
C21 . C31 . C32 . 121.34(12) yes
C21 . C31 . C39 . 118.75(12) yes
C32 . C31 . C39 . 119.89(12) yes
C31 . C32 . C33 . 120.52(13) yes
C31 . C32 . N48 . 117.03(12) yes
C33 . C32 . N48 . 122.39(13) yes
C32 . C33 . C34 . 119.80(14) yes
C32 . C33 . H331 . 121.1 no
C34 . C33 . H331 . 119.1 no
C33 . C34 . C40 . 122.02(13) yes
C33 . C34 . H341 . 118.0 no
C40 . C34 . H341 . 120.0 no
C36 . C35 . C40 . 121.28(15) yes
C36 . C35 . H351 . 119.9 no
C40 . C35 . H351 . 118.9 no
C35 . C36 . C37 . 120.06(14) yes
C35 . C36 . H361 . 121.0 no
C37 . C36 . H361 . 118.9 no
C36 . C37 . C38 . 120.54(15) yes
C36 . C37 . H371 . 117.8 no
C38 . C37 . H371 . 121.7 no
C37 . C38 . C39 . 120.95(14) yes
C37 . C38 . H381 . 122.0 no
C39 . C38 . H381 . 117.0 no
C31 . C39 . C38 . 122.09(13) yes
C31 . C39 . C40 . 119.24(13) yes
C38 . C39 . C40 . 118.65(13) yes
C39 . C40 . C35 . 118.52(14) yes
C39 . C40 . C34 . 118.53(13) yes
C35 . C40 . C34 . 122.95(14) yes
C2 . N41 . C42 . 126.93(12) yes
C2 . N41 . H411 . 116.1(10) no
C42 . N41 . H411 . 116.9(10) no
N41 . C42 . N43 . 113.91(12) yes
N41 . C42 . O44 . 124.44(15) yes
N43 . C42 . O44 . 121.60(14) yes
C22 . N43 . C42 . 121.85(12) yes
C22 . N43 . H431 . 116.5(10) no
C42 . N43 . H431 . 112.6(10) no
C12 . N45 . C46 . 123.55(12) yes
C12 . N45 . H451 . 118.6(9) no
C46 . N45 . H451 . 116.4(9) no
N45 . C46 . O47 . 121.49(14) yes
N45 . C46 . N48 . 113.80(11) yes
O47 . C46 . N48 . 124.69(14) yes
C32 . N48 . C46 . 129.28(12) yes
C32 . N48 . H481 . 114.3(10) no
C46 . N48 . H481 . 116.1(10) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C33 . H331 . O47 . 121 0.91 2.33 2.900(2) yes
C27 . H271 . O44 1_556 125 0.97 2.52 3.180(2) yes
C25 . H251 . O47 1_455 155 0.96 2.36 3.263(2) yes
N41 . H411 . C19 . 131.4(12) 0.865(15) 2.596(15) 3.234(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
7 1 2 x .
7 -1 2 x .
