# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_1256
_database_code_depnum_ccdc_archive 'CCDC 2051532'
loop_
_audit_author_name
_audit_author_address
'Haiyun Peng'
;CCDC
China
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-06-27 downloaded from the CCDC.
;
_audit_creation_date             2020-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H23 N O3'
_chemical_formula_sum            'C27 H23 N O3'
_chemical_formula_weight         409.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O3 N4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1471(4)
_cell_length_b                   9.2244(3)
_cell_length_c                   14.1426(6)
_cell_angle_alpha                92.216(3)
_cell_angle_beta                 107.400(4)
_cell_angle_gamma                108.470(3)
_cell_volume                     1068.25(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4744
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8060
_cell_measurement_theta_min      5.6810
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6202
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.585
_diffrn_reflns_theta_max         66.585
_diffrn_reflns_theta_min         3.311
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 104.00   1.00    1.00    --   34.48  38.00 -60.00   81
  2  ω     68.00  97.00   1.00    1.00    --   34.48  77.00   0.00   29
  3  ω     39.00  78.00   1.00    1.00    --   34.48  57.00   0.00   39
  4  ω     20.00  95.00   1.00    1.00    --   34.48  57.00  60.00   75
  5  ω    129.00 155.00   1.00    3.00    --  105.88 111.00 150.00   26
  6  ω     58.00 148.00   1.00    3.00    --  105.88 178.00  90.00   90
  7  ω     81.00 173.00   1.00    3.00    --  105.88  77.00 -60.00   92
  8  ω    127.00 173.00   1.00    3.00    --  105.88   0.00 -90.00   46
  9  ω    104.00 166.00   1.00    3.00    --  105.88  61.00 -90.00   62
 10  ω     98.00 173.00   1.00    3.00    --  105.88  61.00-150.00   75
 11  ω     91.00 151.00   1.00    3.00    --  105.88  61.00-180.00   60
 12  ω     75.00 133.00   1.00    3.00    --  105.88 -77.00-180.00   58
 13  ω     88.00 114.00   1.00    3.00    --  105.88-111.00-120.00   26
 14  ω     48.00  88.00   1.00    1.00    --   34.48-125.00-180.00   40
 15  ω     42.00 110.00   1.00    3.00    --  105.88 -45.00   0.00   68
 16  ω     71.00  98.00   1.00    3.00    --  105.88-111.00 120.00   27
 17  ω     41.00 118.00   1.00    3.00    --  105.88 -45.00 150.00   77
 18  ω     37.00 103.00   1.00    3.00    --  105.88 -94.00 150.00   66
 19  ω     55.00 107.00   1.00    3.00    --  105.88 -94.00  30.00   52
 20  ω     38.00  87.00   1.00    1.00    --   34.48-125.00 -30.00   49
 21  ω     19.00 102.00   1.00    1.00    --   34.48  57.00 150.00   83
 22  ω     23.00  69.00   1.00    1.00    --   34.48  57.00-120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134708000
_diffrn_orient_matrix_UB_12      0.0321706000
_diffrn_orient_matrix_UB_13      -0.1037151000
_diffrn_orient_matrix_UB_21      -0.1644244000
_diffrn_orient_matrix_UB_22      0.0273516000
_diffrn_orient_matrix_UB_23      -0.0291344000
_diffrn_orient_matrix_UB_31      0.0901432000
_diffrn_orient_matrix_UB_32      0.1729431000
_diffrn_orient_matrix_UB_33      0.0414126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3441
_reflns_number_total             3749
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.2952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1159
_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
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C16(H16), C20(H20), C5(H5), C4(H4), C19(H19), C1(H1), C17(H17),
 C18(H18), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C25(H25A,H25B,H25C), C13(H13A,H13B,H13C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.04271(12) 0.65217(13) 0.83061(8) 0.0415(3) Uani 1 1 d . . . . .
O2 O 0.20452(12) 0.73098(13) 0.55505(8) 0.0429(3) Uani 1 1 d . . . . .
C21 C 0.35029(17) 0.81681(17) 0.62727(10) 0.0356(3) Uani 1 1 d . . . . .
C14 C 0.33468(17) 0.89910(17) 0.71546(11) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.25429(16) 1.01546(15) 0.67715(10) 0.0433(3) Uani 1 1 d . . . . .
C6 C 0.25865(17) 0.55160(16) 0.83762(10) 0.0358(3) Uani 1 1 d . . . . .
C7 C 0.18518(16) 0.66880(17) 0.80837(10) 0.0348(3) Uani 1 1 d . . . . .
C22 C 0.47441(18) 0.80535(18) 0.59951(11) 0.0395(3) Uani 1 1 d . . . . .
H22 H 0.584964 0.853620 0.634655 0.047 Uiso 1 1 calc R . . . .
C8 C 0.21730(16) 0.79503(17) 0.76140(10) 0.0344(3) Uani 1 1 d . . . . .
C15 C 0.50371(17) 0.99029(16) 0.78998(11) 0.0354(3) Uani 1 1 d . . . . .
C9 C 0.09053(17) 0.85661(18) 0.75325(11) 0.0394(3) Uani 1 1 d . . . . .
O3 O 0.4149(2) 0.55417(18) 0.37148(10) 0.0729(4) Uani 1 1 d . . . . .
C16 C 0.6049(2) 1.11662(19) 0.76185(13) 0.0475(4) Uani 1 1 d . . . . .
H16 H 0.570748 1.140836 0.697535 0.057 Uiso 1 1 calc R . . . .
C20 C 0.55781(19) 0.95599(18) 0.88590(11) 0.0418(3) Uani 1 1 d . . . . .
H20 H 0.492406 0.871755 0.905865 0.050 Uiso 1 1 calc R . . . .
C12 C 0.12370(19) 0.98988(19) 0.70020(12) 0.0439(4) Uani 1 1 d . . . . .
C10 C -0.01385(18) 0.7681(2) 0.79590(11) 0.0435(4) Uani 1 1 d . . . . .
C5 C 0.3686(2) 0.52838(19) 0.79389(12) 0.0453(4) Uani 1 1 d . . . . .
H5 H 0.396023 0.588894 0.746495 0.054 Uiso 1 1 calc R . . . .
C24 C 0.2409(2) 0.66341(19) 0.48181(11) 0.0441(4) Uani 1 1 d . . . . .
C23 C 0.4050(2) 0.70456(18) 0.50525(11) 0.0424(4) Uani 1 1 d . . . . .
C4 C 0.2195(2) 0.4591(2) 0.90812(13) 0.0491(4) Uani 1 1 d . . . . .
H4 H 0.145954 0.472465 0.938010 0.059 Uiso 1 1 calc R . . . .
C11 C -0.1670(2) 0.7669(3) 0.81186(15) 0.0645(5) Uani 1 1 d . . . . .
H11A H -0.258077 0.688769 0.763568 0.097 Uiso 1 1 calc GR . . . .
H11B H -0.178599 0.866071 0.804188 0.097 Uiso 1 1 calc GR . . . .
H11C H -0.163536 0.745246 0.878183 0.097 Uiso 1 1 calc GR . . . .
C26 C 0.4910(2) 0.6507(2) 0.44642(13) 0.0515(4) Uani 1 1 d . . . . .
C19 C 0.7091(2) 1.0466(2) 0.95245(13) 0.0525(4) Uani 1 1 d . . . . .
H19 H 0.744284 1.022671 1.016759 0.063 Uiso 1 1 calc R . . . .
C1 C 0.4372(2) 0.4160(2) 0.82042(14) 0.0521(4) Uani 1 1 d . . . . .
H1 H 0.510405 0.401383 0.790643 0.063 Uiso 1 1 calc R . . . .
C17 C 0.7549(2) 1.2058(2) 0.82830(14) 0.0559(4) Uani 1 1 d . . . . .
H17 H 0.821151 1.289729 0.808599 0.067 Uiso 1 1 calc R . . . .
C18 C 0.8073(2) 1.1713(2) 0.92403(14) 0.0567(5) Uani 1 1 d . . . . .
H18 H 0.908293 1.232077 0.968966 0.068 Uiso 1 1 calc R . . . .
C2 C 0.3981(2) 0.3255(2) 0.89051(14) 0.0543(4) Uani 1 1 d . . . . .
H2 H 0.444728 0.250157 0.908314 0.065 Uiso 1 1 calc R . . . .
C3 C 0.2895(3) 0.3475(2) 0.93391(15) 0.0592(5) Uani 1 1 d . . . . .
H3 H 0.262803 0.286544 0.981275 0.071 Uiso 1 1 calc R . . . .
C25 C 0.0993(2) 0.5643(2) 0.39667(14) 0.0620(5) Uani 1 1 d . . . . .
H25A H 0.070698 0.459137 0.409202 0.093 Uiso 1 1 calc GR . . . .
H25B H 0.127178 0.571036 0.336322 0.093 Uiso 1 1 calc GR . . . .
H25C H 0.008288 0.598614 0.389333 0.093 Uiso 1 1 calc GR . . . .
C13 C 0.0209(2) 1.0899(2) 0.67453(17) 0.0647(5) Uani 1 1 d . . . . .
H13A H 0.072506 1.174167 0.644456 0.097 Uiso 1 1 calc GR . . . .
H13B H 0.008769 1.129724 0.734379 0.097 Uiso 1 1 calc GR . . . .
H13C H -0.084642 1.029879 0.628279 0.097 Uiso 1 1 calc GR . . . .
C27 C 0.6725(3) 0.7161(3) 0.48099(17) 0.0668(5) Uani 1 1 d . . . . .
H27A H 0.713243 0.657221 0.444540 0.100 Uiso 1 1 calc GR . . . .
H27B H 0.714619 0.711807 0.551262 0.100 Uiso 1 1 calc GR . . . .
H27C H 0.706694 0.821663 0.469460 0.100 Uiso 1 1 calc GR . . . .


_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
O1 C7 1.3939(16) . ?
O1 C10 1.3752(19) . ?
O2 C21 1.3791(17) . ?
O2 C24 1.3638(19) . ?
C21 C14 1.501(2) . ?
C21 C22 1.339(2) . ?
C14 N1 1.5144(18) . ?
C14 C8 1.520(2) . ?
C14 C15 1.530(2) . ?
N1 C12 1.284(2) . ?
C6 C7 1.456(2) . ?
C6 C5 1.392(2) . ?
C6 C4 1.391(2) . ?
C7 C8 1.358(2) . ?
C22 C23 1.438(2) . ?
C8 C9 1.422(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.384(2) . ?
C9 C12 1.462(2) . ?
C9 C10 1.353(2) . ?
O3 C26 1.222(2) . ?
C16 C17 1.377(2) . ?
C20 C19 1.388(2) . ?
C12 C13 1.496(2) . ?
C10 C11 1.481(2) . ?
C5 C1 1.383(2) . ?
C24 C23 1.356(2) . ?
C24 C25 1.481(2) . ?
C23 C26 1.472(2) . ?
C4 C3 1.382(2) . ?
C26 C27 1.488(3) . ?
C19 C18 1.375(3) . ?
C1 C2 1.376(2) . ?
C17 C18 1.380(3) . ?
C2 C3 1.374(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
C10 O1 C7 108.66(11) . . ?
C24 O2 C21 107.33(12) . . ?
O2 C21 C14 115.08(12) . . ?
C22 C21 O2 109.45(13) . . ?
C22 C21 C14 135.47(14) . . ?
C21 C14 N1 107.53(11) . . ?
C21 C14 C8 113.38(12) . . ?
C21 C14 C15 110.26(11) . . ?
N1 C14 C8 103.30(11) . . ?
N1 C14 C15 107.03(11) . . ?
C8 C14 C15 114.67(11) . . ?
C12 N1 C14 109.82(13) . . ?
C5 C6 C7 120.18(13) . . ?
C4 C6 C7 121.29(13) . . ?
C4 C6 C5 118.52(14) . . ?
O1 C7 C6 115.69(12) . . ?
C8 C7 O1 107.85(12) . . ?
C8 C7 C6 136.45(13) . . ?
C21 C22 C23 107.29(13) . . ?
C7 C8 C14 145.67(13) . . ?
C7 C8 C9 107.22(13) . . ?
C9 C8 C14 107.09(12) . . ?
C16 C15 C14 118.92(13) . . ?
C20 C15 C14 122.48(13) . . ?
C20 C15 C16 118.55(14) . . ?
C8 C9 C12 106.84(13) . . ?
C10 C9 C8 108.32(14) . . ?
C10 C9 C12 144.83(14) . . ?
C17 C16 C15 120.69(16) . . ?
C15 C20 C19 120.39(15) . . ?
N1 C12 C9 112.85(13) . . ?
N1 C12 C13 121.83(16) . . ?
C9 C12 C13 125.32(15) . . ?
O1 C10 C11 116.08(15) . . ?
C9 C10 O1 107.94(12) . . ?
C9 C10 C11 135.98(16) . . ?
C1 C5 C6 120.48(15) . . ?
O2 C24 C25 115.80(15) . . ?
C23 C24 O2 109.95(13) . . ?
C23 C24 C25 134.25(16) . . ?
C22 C23 C26 128.02(15) . . ?
C24 C23 C22 105.97(14) . . ?
C24 C23 C26 125.98(16) . . ?
C3 C4 C6 120.24(15) . . ?
O3 C26 C23 120.61(18) . . ?
O3 C26 C27 121.15(17) . . ?
C23 C26 C27 118.24(16) . . ?
C18 C19 C20 120.51(16) . . ?
C2 C1 C5 120.55(16) . . ?
C16 C17 C18 120.34(16) . . ?
C19 C18 C17 119.52(16) . . ?
C3 C2 C1 119.33(16) . . ?
C2 C3 C4 120.88(16) . . ?

_olex2_date_sample_data_collection 2020-11-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.888
_oxdiff_exptl_absorpt_empirical_full_min 0.533
