# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 1868340'
_audit_update_record             
;
2018-09-18 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C44 H34 N4 O'
_chemical_formula_moiety         'C44 H34 N4 O'
_chemical_formula_weight         634.78
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_as_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'
'-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                   19.1394(8)
_cell_length_b                   8.9002(3)
_cell_length_c                   19.2392(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.390(4)
_cell_angle_gamma                90.0000
_cell_volume                     3127.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8522
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.61
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            paleyellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336.00
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_T_max  0.984

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            15421
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_theta_max         30.630
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_full        30.630
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measured_fraction_theta_full 0.816
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3947
_reflns_number_gt                3530
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1453
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3947
_refine_ls_number_parameters     231
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0838P)²+3.7009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.012
_refine_diff_density_max         1.69
_refine_diff_density_min         -0.46
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0000 0.3950(2) 0.2500 0.0398(4) Uiso 1 2 d S . .
N1 N 0.07421(6) 0.13556(13) 0.48935(6) 0.0151(2) Uani 1 1 d . . .
N2 N 0.01874(7) 0.17804(14) 0.36946(6) 0.0186(3) Uani 1 1 d . . .
C1 C 0.11162(7) 0.04815(15) 0.45135(7) 0.0157(3) Uani 1 1 d . . .
C2 C 0.16811(8) -0.05676(16) 0.47281(8) 0.0182(3) Uani 1 1 d . . .
H2 H 0.1907 -0.0801 0.5227 0.022 Uiso 1 1 calc R . .
C3 C 0.18971(8) -0.12519(16) 0.41800(8) 0.0202(3) Uani 1 1 d . . .
H3 H 0.2276 -0.1982 0.4306 0.024 Uiso 1 1 calc R . .
C4 C 0.15730(8) -0.08991(17) 0.34442(8) 0.0221(3) Uani 1 1 d . . .
H4 H 0.1749 -0.1367 0.3086 0.027 Uiso 1 1 calc R . .
C5 C 0.10020(8) 0.01156(17) 0.32291(8) 0.0215(3) Uani 1 1 d . . .
H5 H 0.0779 0.0344 0.2729 0.026 Uiso 1 1 calc R . .
C6 C 0.07637(7) 0.07931(16) 0.37738(7) 0.0175(3) Uani 1 1 d . . .
C7 C 0.01865(7) 0.20727(15) 0.43688(7) 0.0160(3) Uani 1 1 d . . .
C8 C -0.03224(7) 0.29822(15) 0.45960(7) 0.0159(3) Uani 1 1 d . . .
C9 C -0.08975(8) 0.37093(16) 0.40766(8) 0.0190(3) Uani 1 1 d . . .
H9 H -0.0952 0.3598 0.3572 0.023 Uiso 1 1 calc R . .
C10 C -0.13823(8) 0.45829(16) 0.43016(8) 0.0215(3) Uani 1 1 d . . .
H10 H -0.1771 0.5080 0.3952 0.026 Uiso 1 1 calc R . .
C11 C -0.13018(8) 0.47384(17) 0.50454(8) 0.0216(3) Uani 1 1 d . . .
H11 H -0.1637 0.5346 0.5197 0.026 Uiso 1 1 calc R . .
C12 C -0.07435(8) 0.40225(16) 0.55601(8) 0.0196(3) Uani 1 1 d . . .
H12 H -0.0700 0.4136 0.6062 0.024 Uiso 1 1 calc R . .
C13 C -0.02347(7) 0.31202(15) 0.53472(7) 0.0161(3) Uani 1 1 d . . .
C14 C 0.03818(7) 0.24050(15) 0.58733(7) 0.0161(3) Uani 1 1 d . . .
C15 C 0.08677(7) 0.15769(15) 0.56443(7) 0.0154(3) Uani 1 1 d . . .
C16 C 0.15800(8) 0.10049(15) 0.61252(7) 0.0166(3) Uani 1 1 d . . .
C17 C 0.16170(8) -0.01996(16) 0.65949(7) 0.0206(3) Uani 1 1 d . . .
H17 H 0.1180 -0.0672 0.6619 0.025 Uiso 1 1 calc R . .
C18 C 0.22935(9) -0.07157(19) 0.70297(8) 0.0271(3) Uani 1 1 d . . .
H18 H 0.2317 -0.1541 0.7349 0.033 Uiso 1 1 calc R . .
C19 C 0.29336(9) -0.00273(19) 0.69972(9) 0.0288(4) Uani 1 1 d . . .
H19 H 0.3394 -0.0383 0.7293 0.035 Uiso 1 1 calc R . .
C20 C 0.29008(8) 0.11802(18) 0.65326(9) 0.0250(3) Uani 1 1 d . . .
H20 H 0.3339 0.1656 0.6513 0.030 Uiso 1 1 calc R . .
C21 C 0.22286(8) 0.16927(16) 0.60971(8) 0.0204(3) Uani 1 1 d . . .
H21 H 0.2208 0.2516 0.5777 0.024 Uiso 1 1 calc R . .
C22 C 0.04899(8) 0.26718(18) 0.66711(7) 0.0214(3) Uani 1 1 d . . .
H221 H 0.0092(12) 0.216(3) 0.6834(12) 0.038(6) Uiso 1 1 d . . .
H222 H 0.0985(12) 0.229(3) 0.6984(12) 0.036(5) Uiso 1 1 d . . .
H223 H 0.0455(11) 0.376(2) 0.6782(11) 0.029(5) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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
N1 C7 1.3841(16) . ?
N1 C1 1.4019(17) . ?
N1 C15 1.4056(16) . ?
N2 C7 1.3234(18) . ?
N2 C6 1.3827(18) . ?
C1 C2 1.3944(19) . ?
C1 C6 1.4083(19) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3983(19) . ?
C5 H5 0.9500 . ?
C7 C8 1.4316(19) . ?
C8 C9 1.4042(18) . ?
C8 C13 1.4096(18) . ?
C9 C10 1.376(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4140(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.4519(19) . ?
C14 C15 1.3591(19) . ?
C14 C22 1.5050(18) . ?
C15 C16 1.4899(18) . ?
C16 C17 1.3902(19) . ?
C16 C21 1.399(2) . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H221 1.01(2) . ?
C22 H222 1.02(2) . ?
C22 H223 1.00(2) . ?

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
C7 N1 C1 106.04(11) . . ?
C7 N1 C15 122.90(11) . . ?
C1 N1 C15 131.04(11) . . ?
C7 N2 C6 104.57(11) . . ?
C2 C1 N1 133.54(12) . . ?
C2 C1 C6 121.73(13) . . ?
N1 C1 C6 104.64(11) . . ?
C3 C2 C1 116.80(13) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.91(13) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.36(13) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.59(13) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
N2 C6 C5 128.28(13) . . ?
N2 C6 C1 111.22(12) . . ?
C5 C6 C1 120.49(13) . . ?
N2 C7 N1 113.48(12) . . ?
N2 C7 C8 127.64(12) . . ?
N1 C7 C8 118.85(12) . . ?
C9 C8 C13 121.15(12) . . ?
C9 C8 C7 120.23(12) . . ?
C13 C8 C7 118.62(12) . . ?
C10 C9 C8 119.70(13) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.93(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.95(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.53(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 117.73(12) . . ?
C8 C13 C14 119.96(12) . . ?
C12 C13 C14 122.25(13) . . ?
C15 C14 C13 120.27(12) . . ?
C15 C14 C22 121.15(12) . . ?
C13 C14 C22 118.50(12) . . ?
C14 C15 N1 119.06(12) . . ?
C14 C15 C16 124.88(12) . . ?
N1 C15 C16 115.72(11) . . ?
C17 C16 C21 119.28(13) . . ?
C17 C16 C15 121.77(13) . . ?
C21 C16 C15 118.95(12) . . ?
C16 C17 C18 120.15(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.15(15) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.03(14) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 119.97(15) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.43(14) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C14 C22 H221 111.0(12) . . ?
C14 C22 H222 111.7(12) . . ?
H221 C22 H222 108.6(17) . . ?
C14 C22 H223 112.0(11) . . ?
H221 C22 H223 105.3(18) . . ?
H222 C22 H223 108.0(17) . . ?

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
C7 N1 C1 C2 -174.18(15) . . . . ?
C15 N1 C1 C2 7.5(2) . . . . ?
C7 N1 C1 C6 2.12(14) . . . . ?
C15 N1 C1 C6 -176.18(13) . . . . ?
N1 C1 C2 C3 177.98(14) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C7 N2 C6 C5 179.27(14) . . . . ?
C7 N2 C6 C1 0.18(16) . . . . ?
C4 C5 C6 N2 -176.78(14) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C2 C1 C6 N2 175.37(13) . . . . ?
N1 C1 C6 N2 -1.48(15) . . . . ?
C2 C1 C6 C5 -3.8(2) . . . . ?
N1 C1 C6 C5 179.35(13) . . . . ?
C6 N2 C7 N1 1.28(16) . . . . ?
C6 N2 C7 C8 -176.87(13) . . . . ?
C1 N1 C7 N2 -2.23(16) . . . . ?
C15 N1 C7 N2 176.24(12) . . . . ?
C1 N1 C7 C8 176.10(12) . . . . ?
C15 N1 C7 C8 -5.43(19) . . . . ?
N2 C7 C8 C9 -1.1(2) . . . . ?
N1 C7 C8 C9 -179.20(12) . . . . ?
N2 C7 C8 C13 178.47(13) . . . . ?
N1 C7 C8 C13 0.41(19) . . . . ?
C13 C8 C9 C10 0.5(2) . . . . ?
C7 C8 C9 C10 -179.87(13) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C7 C8 C13 C12 -179.94(12) . . . . ?
C9 C8 C13 C14 -177.54(12) . . . . ?
C7 C8 C13 C14 2.85(19) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C11 C12 C13 C14 176.99(13) . . . . ?
C8 C13 C14 C15 -1.3(2) . . . . ?
C12 C13 C14 C15 -178.39(13) . . . . ?
C8 C13 C14 C22 175.46(12) . . . . ?
C12 C13 C14 C22 -1.6(2) . . . . ?
C13 C14 C15 N1 -3.48(19) . . . . ?
C22 C14 C15 N1 179.84(12) . . . . ?
C13 C14 C15 C16 169.48(12) . . . . ?
C22 C14 C15 C16 -7.2(2) . . . . ?
C7 N1 C15 C14 7.03(19) . . . . ?
C1 N1 C15 C14 -174.92(13) . . . . ?
C7 N1 C15 C16 -166.56(12) . . . . ?
C1 N1 C15 C16 11.5(2) . . . . ?
C14 C15 C16 C17 74.47(19) . . . . ?
N1 C15 C16 C17 -112.36(15) . . . . ?
C14 C15 C16 C21 -106.11(16) . . . . ?
N1 C15 C16 C21 67.06(17) . . . . ?
C21 C16 C17 C18 -0.2(2) . . . . ?
C15 C16 C17 C18 179.18(13) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C19 C20 C21 C16 0.4(2) . . . . ?
C17 C16 C21 C20 0.0(2) . . . . ?
C15 C16 C21 C20 -179.45(13) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        4j
