# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelxt_a
_database_code_depnum_ccdc_archive 'CCDC 2060961'
loop_
_audit_author_name
_audit_author_address
'Kazuki Ishizaki'
;Waseda University
Japan
;
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H33 N O'
_chemical_formula_sum            'C27 H33 N O'
_chemical_formula_weight         387.54
_chemical_absolute_configuration syn
_chemical_melting_point          397
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'
N N 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3282(8)
_cell_length_b                   9.8266(12)
_cell_length_c                   39.383(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2449.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13137
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.07
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR(Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            29817
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'Â\/Yw scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2741
_reflns_number_total             4483
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.2160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_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. Uiso/Uaniso restraints and constraints
C00H \\sim C0AA \\sim C00U \\sim C1AA: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C00H \\sim C00S \\sim C00T \\sim C00R: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 C00H, C0AA, C00U, C1AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00H, C00S, C00T, C00R
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=Sof(C00U)=Sof(H1AA)=Sof(HD)=Sof(HE)=
 Sof(C1AA)=Sof(H1AB)=Sof(H1AC)=Sof(H1AD)=1-FVAR(1)
 Sof(C00R)=Sof(H00W)=Sof(H00X)=Sof(H00Y)=Sof(C00S)=Sof(H00Z)=Sof(H)=Sof(HA)=
 Sof(C00T)=Sof(H00)=Sof(HB)=Sof(HC)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00I(H00I)
5.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L)
5.c Idealised Me refined as rotating group:
 C00N(H00B,H00H,H00M), C00O(H00N,H00O,H00P), C00P(H00Q,H00R,H00S), C00Q(H00T,
 H00U,H00V), C00R(H00W,H00X,H00Y), C00S(H00Z,H,HA), C00T(H00,HB,HC), C0AA(H0AA,
 H0AB,H0AC), C00U(H1AA,HD,HE), C1AA(H1AB,H1AC,H1AD)
5.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.3420(5) 0.7830(3) 0.36019(6) 0.0903(8) Uani 1 1 d . . . . .
H001 H 0.409398 0.802726 0.377278 0.135 Uiso 1 1 calc GR . . . .
N002 N 0.5981(6) 0.7509(3) 0.41102(8) 0.0819(9) Uani 1 1 d . . . . .
C003 C 0.3567(7) 0.6469(4) 0.35444(9) 0.0731(11) Uani 1 1 d . . . . .
C004 C 0.4263(6) 1.0806(4) 0.50633(10) 0.0788(11) Uani 1 1 d . . . . .
C005 C 0.2411(7) 0.5892(4) 0.32783(9) 0.0809(11) Uani 1 1 d . . . . .
C006 C 0.5822(7) 0.9936(4) 0.51885(10) 0.0785(10) Uani 1 1 d . . . . .
C007 C 0.4850(7) 0.5672(4) 0.37495(9) 0.0736(10) Uani 1 1 d . . . . .
C008 C 0.3933(8) 0.3664(4) 0.34284(9) 0.0803(11) Uani 1 1 d . . . . .
C009 C 0.2654(8) 0.4496(4) 0.32326(10) 0.0881(13) Uani 1 1 d . . . . .
H009 H 0.189853 0.409049 0.305710 0.106 Uiso 1 1 calc R . . . .
C00A C 0.5021(7) 0.4275(4) 0.36880(10) 0.0804(11) Uani 1 1 d . . . . .
H00A H 0.589040 0.374979 0.382601 0.097 Uiso 1 1 calc R . . . .
C00B C 0.6174(7) 0.8907(4) 0.46298(9) 0.0760(10) Uani 1 1 d . . . . .
C00C C 0.3374(8) 1.1782(5) 0.52904(13) 0.0999(14) Uani 1 1 d . . . . .
H00C H 0.230149 1.235305 0.521443 0.120 Uiso 1 1 calc R . . . .
C00D C 0.6723(7) 0.8976(4) 0.49611(10) 0.0885(12) Uani 1 1 d . . . . .
H00D H 0.773015 0.837024 0.504331 0.106 Uiso 1 1 calc R . . . .
C00E C 0.4587(7) 0.9777(5) 0.45125(11) 0.0911(13) Uani 1 1 d . . . . .
H00E H 0.415876 0.972747 0.428690 0.109 Uiso 1 1 calc R . . . .
C00F C 0.4060(9) 1.1890(5) 0.56112(13) 0.1047(15) Uani 1 1 d . . . . .
H00F H 0.350674 1.256133 0.575204 0.126 Uiso 1 1 calc R . . . .
C00G C 0.6042(7) 0.6255(4) 0.40319(9) 0.0813(11) Uani 1 1 d . . . . .
H00G H 0.688833 0.567943 0.416088 0.098 Uiso 1 1 calc R . . . .
C00H C 0.4056(9) 0.2123(4) 0.33593(11) 0.0967(13) Uani 1 1 d . U . . .
C00I C 0.7346(7) 0.7960(5) 0.43890(10) 0.0902(13) Uani 1 1 d . . . . .
H00I H 0.785294 0.716516 0.451509 0.108 Uiso 1 1 calc R . . . .
C00J C 0.3655(8) 1.0701(5) 0.47255(12) 0.0995(13) Uani 1 1 d . . . . .
H00J H 0.259752 1.126812 0.464258 0.119 Uiso 1 1 calc R . . . .
C00K C 0.5580(10) 1.1014(6) 0.57341(13) 0.1192(17) Uani 1 1 d . . . . .
H00K H 0.601587 1.107459 0.595909 0.143 Uiso 1 1 calc R . . . .
C00L C 0.6437(9) 1.0063(5) 0.55264(11) 0.1105(16) Uani 1 1 d . . . . .
H00L H 0.746348 0.947935 0.561202 0.133 Uiso 1 1 calc R . . . .
C00M C 0.1011(10) 0.6740(5) 0.30441(11) 0.1059(16) Uani 1 1 d . . . . .
C00N C 0.2439(12) 0.7745(6) 0.28504(11) 0.144(2) Uani 1 1 d . . . . .
H00B H 0.311151 0.834708 0.300898 0.216 Uiso 1 1 calc GR . . . .
H00H H 0.159849 0.826494 0.269446 0.216 Uiso 1 1 calc GR . . . .
H00M H 0.349632 0.724799 0.272716 0.216 Uiso 1 1 calc GR . . . .
C00O C -0.0660(10) 0.7533(7) 0.32454(14) 0.139(2) Uani 1 1 d . . . . .
H00N H -0.156471 0.690611 0.336273 0.209 Uiso 1 1 calc GR . . . .
H00O H -0.148731 0.807542 0.309222 0.209 Uiso 1 1 calc GR . . . .
H00P H 0.002729 0.811543 0.340706 0.209 Uiso 1 1 calc GR . . . .
C00P C 0.9231(8) 0.8704(6) 0.42314(15) 0.141(2) Uani 1 1 d . . . . .
H00Q H 1.002302 0.808155 0.409304 0.212 Uiso 1 1 calc GR . . . .
H00R H 1.012149 0.905247 0.440849 0.212 Uiso 1 1 calc GR . . . .
H00S H 0.873133 0.944286 0.409375 0.212 Uiso 1 1 calc GR . . . .
C00Q C -0.0114(15) 0.5862(6) 0.27776(17) 0.187(4) Uani 1 1 d . . . . .
H00T H 0.091131 0.533963 0.265411 0.280 Uiso 1 1 calc GR . . . .
H00U H -0.087301 0.643937 0.262326 0.280 Uiso 1 1 calc GR . . . .
H00V H -0.108628 0.525830 0.288865 0.280 Uiso 1 1 calc GR . . . .
C00R C 0.484(3) 0.1877(8) 0.2998(2) 0.151(5) Uani 0.749(16) 1 d . U P A 1
H00W H 0.397309 0.237983 0.284115 0.226 Uiso 0.749(16) 1 calc GR . P A 1
H00X H 0.474623 0.092359 0.294600 0.226 Uiso 0.749(16) 1 calc GR . P A 1
H00Y H 0.627638 0.217157 0.297818 0.226 Uiso 0.749(16) 1 calc GR . P A 1
C00S C 0.559(2) 0.1377(8) 0.3596(3) 0.135(4) Uani 0.749(16) 1 d . U P A 1
H00Z H 0.694971 0.180781 0.358701 0.202 Uiso 0.749(16) 1 calc GR . P A 1
H H 0.571717 0.044568 0.352607 0.202 Uiso 0.749(16) 1 calc GR . P A 1
HA H 0.506060 0.141160 0.382479 0.202 Uiso 0.749(16) 1 calc GR . P A 1
C00T C 0.1919(16) 0.1478(9) 0.3395(4) 0.164(6) Uani 0.749(16) 1 d . U P A 1
H00 H 0.128246 0.176950 0.360423 0.247 Uiso 0.749(16) 1 calc GR . P A 1
HB H 0.206744 0.050570 0.339661 0.247 Uiso 0.749(16) 1 calc GR . P A 1
HC H 0.104105 0.174564 0.320811 0.247 Uiso 0.749(16) 1 calc GR . P A 1
C0AA C 0.294(7) 0.1454(17) 0.3674(7) 0.140(12) Uani 0.251(16) 1 d . U P A 2
H0AA H 0.372922 0.165411 0.387588 0.209 Uiso 0.251(16) 1 calc GR . P A 2
H0AB H 0.287179 0.048571 0.364247 0.209 Uiso 0.251(16) 1 calc GR . P A 2
H0AC H 0.153407 0.181145 0.369562 0.209 Uiso 0.251(16) 1 calc GR . P A 2
C00U C 0.275(5) 0.1754(17) 0.3031(6) 0.100(9) Uani 0.251(16) 1 d . U P A 2
H1AA H 0.132035 0.205816 0.305798 0.151 Uiso 0.251(16) 1 calc GR . P A 2
HD H 0.276964 0.078659 0.299834 0.151 Uiso 0.251(16) 1 calc GR . P A 2
HE H 0.337354 0.219373 0.283784 0.151 Uiso 0.251(16) 1 calc GR . P A 2
C1AA C 0.628(5) 0.183(3) 0.3325(11) 0.153(14) Uani 0.251(16) 1 d . U P A 2
H1AB H 0.689920 0.243200 0.316119 0.229 Uiso 0.251(16) 1 calc GR . P A 2
H1AC H 0.645994 0.090280 0.324998 0.229 Uiso 0.251(16) 1 calc GR . P A 2
H1AD H 0.696978 0.194479 0.354006 0.229 Uiso 0.251(16) 1 calc GR . P A 2


_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
O001 C003 1.359(4) . ?
N002 C00G 1.270(5) . ?
N002 C00I 1.466(5) . ?
C003 C005 1.399(5) . ?
C003 C007 1.388(5) . ?
C004 C006 1.395(5) . ?
C004 C00C 1.427(6) . ?
C004 C00J 1.389(6) . ?
C005 C009 1.392(6) . ?
C005 C00M 1.526(6) . ?
C006 C00D 1.421(5) . ?
C006 C00L 1.392(5) . ?
C007 C00A 1.397(5) . ?
C007 C00G 1.461(5) . ?
C008 C009 1.385(6) . ?
C008 C00A 1.371(5) . ?
C008 C00H 1.540(5) . ?
C00B C00D 1.352(5) . ?
C00B C00E 1.397(5) . ?
C00B C00I 1.521(6) . ?
C00C C00F 1.340(6) . ?
C00E C00J 1.370(6) . ?
C00F C00K 1.379(7) . ?
C00H C00R 1.527(9) . ?
C00H C00S 1.534(10) . ?
C00H C00T 1.500(10) . ?
C00H C0AA 1.57(2) . ?
C00H C00U 1.57(2) . ?
C00H C1AA 1.45(3) . ?
C00I C00P 1.530(7) . ?
C00K C00L 1.355(6) . ?
C00M C00N 1.540(8) . ?
C00M C00O 1.535(7) . ?
C00M C00Q 1.534(7) . ?

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
C00G N002 C00I 117.2(4) . . ?
O001 C003 C005 119.2(4) . . ?
O001 C003 C007 119.9(3) . . ?
C007 C003 C005 120.9(3) . . ?
C006 C004 C00C 118.0(4) . . ?
C00J C004 C006 119.3(4) . . ?
C00J C004 C00C 122.7(4) . . ?
C003 C005 C00M 122.4(4) . . ?
C009 C005 C003 116.0(4) . . ?
C009 C005 C00M 121.6(4) . . ?
C004 C006 C00D 117.9(3) . . ?
C00L C006 C004 118.7(4) . . ?
C00L C006 C00D 123.4(4) . . ?
C003 C007 C00A 119.9(3) . . ?
C003 C007 C00G 121.6(4) . . ?
C00A C007 C00G 118.5(4) . . ?
C009 C008 C00H 120.7(4) . . ?
C00A C008 C009 116.8(4) . . ?
C00A C008 C00H 122.5(4) . . ?
C008 C009 C005 125.0(4) . . ?
C008 C00A C007 121.4(4) . . ?
C00D C00B C00E 118.2(4) . . ?
C00D C00B C00I 120.5(4) . . ?
C00E C00B C00I 121.2(3) . . ?
C00F C00C C004 121.1(5) . . ?
C00B C00D C006 122.6(4) . . ?
C00J C00E C00B 120.8(4) . . ?
C00C C00F C00K 120.5(5) . . ?
N002 C00G C007 123.3(4) . . ?
C008 C00H C0AA 104.5(8) . . ?
C008 C00H C00U 110.2(8) . . ?
C00R C00H C008 109.7(4) . . ?
C00R C00H C00S 106.7(7) . . ?
C00S C00H C008 113.2(5) . . ?
C00T C00H C008 110.7(5) . . ?
C00T C00H C00R 108.2(7) . . ?
C00T C00H C00S 108.1(7) . . ?
C0AA C00H C00U 108.4(17) . . ?
C1AA C00H C008 105.3(11) . . ?
C1AA C00H C0AA 115(2) . . ?
C1AA C00H C00U 112.8(17) . . ?
N002 C00I C00B 111.4(3) . . ?
N002 C00I C00P 107.5(4) . . ?
C00B C00I C00P 110.0(4) . . ?
C00E C00J C004 121.1(4) . . ?
C00L C00K C00F 119.9(5) . . ?
C00K C00L C006 121.8(5) . . ?
C005 C00M C00N 108.0(5) . . ?
C005 C00M C00O 111.4(4) . . ?
C005 C00M C00Q 112.1(4) . . ?
C00O C00M C00N 109.5(4) . . ?
C00Q C00M C00N 107.1(5) . . ?
C00Q C00M C00O 108.6(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

