# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_cu_drp149_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2143164'
loop_
_audit_author_name
_audit_author_address
'Daisy Pooler'
;Rijksuniversiteit Groningen
Netherlands
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3794(3)
_cell_length_b                   17.1088(7)
_cell_length_c                   13.8545(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.5930(10)
_cell_angle_gamma                90
_cell_volume                     1707.09(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.45
_cell_measurement_theta_min      4.17
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0924 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.9112.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34704
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.442
_diffrn_reflns_theta_min         4.167
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3116
_reflns_number_total             3342
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.261
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.070
_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)+(0.0416P)²+0.6936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C19(H19), C18(H18), C7(H7), C4(H4), C13(H13), C6(H6), C17(H17),
 C5(H5), C16(H16)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
O1 O 0.99733(11) 0.89864(5) 0.54471(6) 0.0219(2) Uani 1 1 d . . . . .
N1 N 0.76708(13) 0.96792(6) 0.44125(7) 0.0194(2) Uani 1 1 d . . . . .
H1 H 0.834245 1.008226 0.430653 0.023 Uiso 1 1 calc R . . . .
N2 N 0.20071(16) 0.44794(6) 0.57900(8) 0.0301(3) Uani 1 1 d . . . . .
C1 C 0.67943(15) 0.84690(6) 0.48847(8) 0.0181(2) Uani 1 1 d . . . . .
C2 C 0.83491(15) 0.90511(6) 0.49795(8) 0.0187(2) Uani 1 1 d . . . . .
C8 C 0.51690(15) 0.88638(6) 0.42777(8) 0.0178(2) Uani 1 1 d . . . . .
C15 C 0.34813(15) 0.60866(6) 0.45705(8) 0.0184(2) Uani 1 1 d . . . . .
C3 C 0.57657(15) 0.96004(6) 0.40200(8) 0.0183(2) Uani 1 1 d . . . . .
C21 C 0.57415(15) 0.70952(6) 0.52708(8) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.70235(15) 0.77652(7) 0.53521(8) 0.0181(2) Uani 1 1 d . . . . .
C20 C 0.44978(15) 0.67711(6) 0.44289(8) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.37738(16) 0.57478(7) 0.55342(9) 0.0200(2) Uani 1 1 d . . . . .
C19 C 0.43437(16) 0.70524(6) 0.34531(8) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.504636 0.749570 0.334198 0.023 Uiso 1 1 calc R . . . .
C18 C 0.31959(16) 0.66945(7) 0.26673(8) 0.0217(3) Uani 1 1 d . . . . .
H18 H 0.311302 0.689006 0.201740 0.026 Uiso 1 1 calc R . . . .
C12 C 0.60817(16) 0.67090(7) 0.61712(8) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.32736(16) 0.86956(7) 0.40325(8) 0.0204(2) Uani 1 1 d . . . . .
H7 H 0.281851 0.821634 0.423256 0.025 Uiso 1 1 calc R . . . .
C4 C 0.45739(16) 1.01457(7) 0.34843(8) 0.0207(2) Uani 1 1 d . . . . .
H4 H 0.501551 1.063673 0.331239 0.025 Uiso 1 1 calc R . . . .
C13 C 0.50676(16) 0.60431(7) 0.63199(8) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.526929 0.580008 0.695091 0.026 Uiso 1 1 calc R . . . .
C6 C 0.20573(16) 0.92393(7) 0.34907(9) 0.0223(3) Uani 1 1 d . . . . .
H6 H 0.076818 0.912381 0.331297 0.027 Uiso 1 1 calc R . . . .
C17 C 0.21358(16) 0.60372(7) 0.28167(9) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.132142 0.580054 0.226875 0.027 Uiso 1 1 calc R . . . .
C5 C 0.26999(16) 0.99484(7) 0.32056(8) 0.0218(3) Uani 1 1 d . . . . .
H5 H 0.185155 1.030251 0.281637 0.026 Uiso 1 1 calc R . . . .
C23 C 0.27758(16) 0.50447(7) 0.56749(9) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.22732(16) 0.57395(7) 0.37433(9) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.155453 0.529618 0.383583 0.026 Uiso 1 1 calc R . . . .
C10 C 0.86534(15) 0.75633(7) 0.61995(8) 0.0200(3) Uani 1 1 d . . . . .
H10 H 0.921093 0.804852 0.654357 0.024 Uiso 1 1 calc R . . . .
C11 C 0.76865(17) 0.70755(7) 0.68835(9) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.853264 0.667221 0.724476 0.029 Uiso 1 1 calc R . . . .
H11B H 0.724920 0.741298 0.736676 0.029 Uiso 1 1 calc R . . . .
C22 C 1.01315(17) 0.70828(7) 0.58387(10) 0.0273(3) Uani 1 1 d . . . . .
H22A H 0.954838 0.662460 0.547381 0.041 Uiso 1 1 calc GR . . . .
H22B H 1.108316 0.691152 0.640849 0.041 Uiso 1 1 calc GR . . . .
H22C H 1.070735 0.740523 0.540340 0.041 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 C2 1.2369(14) . ?
N1 C2 1.3605(15) . ?
N1 C3 1.3989(14) . ?
N2 C23 1.1497(16) . ?
C1 C2 1.5032(15) . ?
C1 C8 1.4704(15) . ?
C1 C9 1.3603(16) . ?
C8 C3 1.4066(16) . ?
C8 C7 1.3954(16) . ?
C15 C20 1.4270(16) . ?
C15 C14 1.4282(16) . ?
C15 C16 1.4197(16) . ?
C3 C4 1.3821(16) . ?
C21 C9 1.4749(15) . ?
C21 C20 1.4295(15) . ?
C21 C12 1.3853(16) . ?
C9 C10 1.5259(15) . ?
C20 C19 1.4161(16) . ?
C14 C13 1.3779(17) . ?
C14 C23 1.4457(16) . ?
C19 C18 1.3696(16) . ?
C18 C17 1.4105(17) . ?
C12 C13 1.4027(16) . ?
C12 C11 1.5032(16) . ?
C7 C6 1.3931(17) . ?
C4 C5 1.3937(17) . ?
C6 C5 1.3909(17) . ?
C17 C16 1.3643(17) . ?
C10 C11 1.5488(16) . ?
C10 C22 1.5341(16) . ?

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
C2 N1 C3 111.12(9) . . ?
C8 C1 C2 104.93(9) . . ?
C9 C1 C2 122.11(10) . . ?
C9 C1 C8 132.85(10) . . ?
O1 C2 N1 124.45(10) . . ?
O1 C2 C1 128.35(10) . . ?
N1 C2 C1 107.16(9) . . ?
C3 C8 C1 107.17(9) . . ?
C7 C8 C1 133.93(11) . . ?
C7 C8 C3 118.40(10) . . ?
C20 C15 C14 119.00(10) . . ?
C16 C15 C20 119.26(10) . . ?
C16 C15 C14 121.68(10) . . ?
N1 C3 C8 109.35(10) . . ?
C4 C3 N1 127.71(10) . . ?
C4 C3 C8 122.91(10) . . ?
C20 C21 C9 130.60(10) . . ?
C12 C21 C9 108.34(10) . . ?
C12 C21 C20 120.52(10) . . ?
C1 C9 C21 129.84(10) . . ?
C1 C9 C10 124.19(10) . . ?
C21 C9 C10 105.53(9) . . ?
C15 C20 C21 117.99(10) . . ?
C19 C20 C15 118.36(10) . . ?
C19 C20 C21 123.42(10) . . ?
C15 C14 C23 119.09(10) . . ?
C13 C14 C15 121.81(10) . . ?
C13 C14 C23 118.96(10) . . ?
C18 C19 C20 120.92(11) . . ?
C19 C18 C17 120.43(11) . . ?
C21 C12 C13 121.46(10) . . ?
C21 C12 C11 110.76(10) . . ?
C13 C12 C11 127.70(10) . . ?
C6 C7 C8 119.17(11) . . ?
C3 C4 C5 117.52(11) . . ?
C14 C13 C12 118.80(10) . . ?
C5 C6 C7 121.06(11) . . ?
C16 C17 C18 120.39(11) . . ?
C6 C5 C4 120.78(11) . . ?
N2 C23 C14 178.96(13) . . ?
C17 C16 C15 120.54(11) . . ?
C9 C10 C11 101.64(9) . . ?
C9 C10 C22 111.58(9) . . ?
C22 C10 C11 111.45(10) . . ?
C12 C11 C10 103.01(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_drp229_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2143240'
loop_
_audit_author_name
_audit_author_address
'Daisy Pooler'
;Rijksuniversiteit Groningen
Netherlands
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-08-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N2 O'
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1398(4)
_cell_length_b                   8.6168(3)
_cell_length_c                   21.2050(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.3040(10)
_cell_angle_gamma                90
_cell_volume                     2018.94(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.02
_cell_measurement_theta_min      5.55
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5968
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1211 before and 0.0728 after correction.
The Ratio of minimum to maximum transmission is 0.7919.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34820
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.043
_diffrn_reflns_theta_min         5.548
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3670
_reflns_number_total             3922
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.088
_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)+(0.0699P)²+1.5564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1472
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C19(H19), C20(H20), C12(H12), C22(H22), C6(H6), C7(H7), C11(H11),
 C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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
O1 O 0.93385(10) -0.06244(13) 0.57615(5) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.89827(12) 0.14785(15) 0.51013(6) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.917688 0.104816 0.475176 0.023 Uiso 1 1 calc R U . . .
C18 C 0.83204(13) 0.33029(18) 0.57623(7) 0.0166(3) Uani 1 1 d . . . . .
C15 C 0.82300(13) 0.14597(17) 0.67101(7) 0.0167(3) Uani 1 1 d . . . . .
C16 C 0.84591(13) 0.18227(17) 0.61115(7) 0.0164(3) Uani 1 1 d . . . . .
C17 C 0.89736(14) 0.07153(18) 0.56664(7) 0.0172(3) Uani 1 1 d . . . . .
C23 C 0.86452(13) 0.30218(18) 0.51510(7) 0.0168(3) Uani 1 1 d . . . . .
C14 C 0.76993(14) 0.25889(17) 0.71178(7) 0.0181(3) Uani 1 1 d . . . . .
C21 C 0.83324(14) 0.56636(19) 0.48642(7) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.83801(15) 0.7890(2) 0.40588(8) 0.0350(4) Uani 1 1 d . . . . .
C19 C 0.80369(14) 0.48163(18) 0.59217(7) 0.0192(3) Uani 1 1 d . . . . .
H19 H 0.783854 0.504340 0.633451 0.023 Uiso 1 1 calc R U . . .
C13 C 0.65702(15) 0.33650(18) 0.69411(8) 0.0207(3) Uani 1 1 d . . . . .
C20 C 0.80461(14) 0.59937(18) 0.54727(8) 0.0210(3) Uani 1 1 d . . . . .
H20 H 0.785661 0.702730 0.558071 0.025 Uiso 1 1 calc R U . . .
C24 C 0.83548(15) 0.6914(2) 0.44108(8) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.89820(16) 0.01405(19) 0.77502(7) 0.0217(3) Uani 1 1 d . . . . .
H3A H 0.829082 -0.008651 0.798649 0.026 Uiso 1 1 calc R U . . .
H3B H 0.964028 -0.059853 0.789479 0.026 Uiso 1 1 calc R U . . .
C1 C 0.85852(15) -0.00841(17) 0.70287(7) 0.0183(3) Uani 1 1 d . . . . .
H1 H 0.928438 -0.051864 0.683354 0.022 Uiso 1 1 calc R U . . .
C4 C 0.94224(16) 0.17990(19) 0.78961(7) 0.0218(3) Uani 1 1 d . . . . .
H4A H 0.970573 0.191427 0.835545 0.026 Uiso 1 1 calc R U . . .
H4B H 1.010164 0.205057 0.765463 0.026 Uiso 1 1 calc R U . . .
C5 C 0.83674(15) 0.28654(18) 0.77027(7) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.57769(15) 0.2980(2) 0.63883(8) 0.0255(4) Uani 1 1 d . . . . .
H12 H 0.598742 0.217021 0.611873 0.031 Uiso 1 1 calc R U . . .
C22 C 0.86408(14) 0.41616(19) 0.46933(7) 0.0196(3) Uani 1 1 d . . . . .
H22 H 0.883852 0.393572 0.428028 0.023 Uiso 1 1 calc R U . . .
C8 C 0.62282(16) 0.4561(2) 0.73476(8) 0.0258(4) Uani 1 1 d . . . . .
C6 C 0.80214(17) 0.4063(2) 0.80967(8) 0.0273(4) Uani 1 1 d . . . . .
H6 H 0.850245 0.428286 0.848923 0.033 Uiso 1 1 calc R U . . .
C2 C 0.75233(16) -0.12272(19) 0.69095(8) 0.0251(4) Uani 1 1 d . . . . .
H2A H 0.681386 -0.078879 0.707468 0.038 Uiso 1 1 calc R U . . .
H2B H 0.774610 -0.220990 0.712606 0.038 Uiso 1 1 calc R U . . .
H2C H 0.733231 -0.141267 0.645180 0.038 Uiso 1 1 calc R U . . .
C7 C 0.69904(18) 0.4911(2) 0.79142(9) 0.0300(4) Uani 1 1 d . . . . .
H7 H 0.678716 0.574610 0.817323 0.036 Uiso 1 1 calc R U . . .
C11 C 0.47088(17) 0.3762(3) 0.62380(10) 0.0353(4) Uani 1 1 d . . . . .
H11 H 0.418221 0.348518 0.586698 0.042 Uiso 1 1 calc R U . . .
C9 C 0.51238(18) 0.5364(2) 0.71693(10) 0.0351(4) Uani 1 1 d . . . . .
H9 H 0.489731 0.618391 0.742950 0.042 Uiso 1 1 calc R U . . .
C10 C 0.43843(18) 0.4975(3) 0.66303(11) 0.0402(5) Uani 1 1 d . . . . .
H10 H 0.364796 0.552299 0.651824 0.048 Uiso 1 1 calc R U . . .


_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 C17 1.232(2) . ?
N2 H2 0.8800 . ?
N2 C17 1.368(2) . ?
N2 C23 1.390(2) . ?
C18 C16 1.473(2) . ?
C18 C23 1.410(2) . ?
C18 C19 1.393(2) . ?
C15 C16 1.362(2) . ?
C15 C14 1.474(2) . ?
C15 C1 1.521(2) . ?
C16 C17 1.506(2) . ?
C23 C22 1.380(2) . ?
C14 C13 1.432(2) . ?
C14 C5 1.384(2) . ?
C21 C20 1.397(2) . ?
C21 C24 1.447(2) . ?
C21 C22 1.399(2) . ?
N1 C24 1.127(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(2) . ?
C13 C12 1.415(2) . ?
C13 C8 1.426(2) . ?
C20 H20 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C1 1.550(2) . ?
C3 C4 1.530(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.507(2) . ?
C5 C6 1.412(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.369(3) . ?
C22 H22 0.9500 . ?
C8 C7 1.413(3) . ?
C8 C9 1.420(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C7 H7 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.412(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.363(3) . ?
C10 H10 0.9500 . ?

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
C17 N2 H2 124.4 . . ?
C17 N2 C23 111.18(12) . . ?
C23 N2 H2 124.4 . . ?
C23 C18 C16 106.89(13) . . ?
C19 C18 C16 134.49(14) . . ?
C19 C18 C23 118.44(14) . . ?
C16 C15 C14 122.10(14) . . ?
C16 C15 C1 123.06(13) . . ?
C14 C15 C1 114.69(13) . . ?
C18 C16 C17 104.92(12) . . ?
C15 C16 C18 130.32(14) . . ?
C15 C16 C17 124.73(14) . . ?
O1 C17 N2 123.70(13) . . ?
O1 C17 C16 129.43(14) . . ?
N2 C17 C16 106.87(13) . . ?
N2 C23 C18 109.74(13) . . ?
C22 C23 N2 127.18(14) . . ?
C22 C23 C18 123.07(14) . . ?
C13 C14 C15 124.00(14) . . ?
C5 C14 C15 115.42(14) . . ?
C5 C14 C13 120.58(14) . . ?
C20 C21 C24 119.16(15) . . ?
C20 C21 C22 121.34(14) . . ?
C22 C21 C24 119.45(15) . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.63(14) . . ?
C20 C19 H19 120.2 . . ?
C12 C13 C14 122.87(15) . . ?
C8 C13 C14 118.20(15) . . ?
C8 C13 C12 118.92(16) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.37(15) . . ?
C19 C20 H20 119.8 . . ?
N1 C24 C21 179.5(2) . . ?
H3A C3 H3B 108.0 . . ?
C1 C3 H3A 109.4 . . ?
C1 C3 H3B 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C4 C3 C1 111.11(12) . . ?
C15 C1 C3 110.77(12) . . ?
C15 C1 H1 108.4 . . ?
C15 C1 C2 109.66(13) . . ?
C3 C1 H1 108.4 . . ?
C2 C1 C3 111.08(13) . . ?
C2 C1 H1 108.4 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 C3 107.19(14) . . ?
C5 C4 H4A 110.3 . . ?
C5 C4 H4B 110.3 . . ?
C14 C5 C4 116.81(14) . . ?
C14 C5 C6 120.02(16) . . ?
C6 C5 C4 123.14(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.68(17) . . ?
C11 C12 H12 119.7 . . ?
C23 C22 C21 117.08(14) . . ?
C23 C22 H22 121.5 . . ?
C21 C22 H22 121.5 . . ?
C13 C8 C9 118.70(17) . . ?
C7 C8 C13 119.38(16) . . ?
C7 C8 C9 121.92(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.20(16) . . ?
C7 C6 H6 119.9 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.07(15) . . ?
C6 C7 H7 119.5 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.49(19) . . ?
C10 C11 H11 119.8 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.94(18) . . ?
C10 C9 H9 119.5 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.23(18) . . ?
C9 C10 H10 119.9 . . ?

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
N2 C23 C22 C21 -176.25(15) . . . . ?
C18 C16 C17 O1 173.41(15) . . . . ?
C18 C16 C17 N2 -6.19(16) . . . . ?
C18 C23 C22 C21 2.0(2) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C15 C16 C17 O1 -4.8(3) . . . . ?
C15 C16 C17 N2 175.58(14) . . . . ?
C15 C14 C13 C12 8.1(2) . . . . ?
C15 C14 C13 C8 -172.86(14) . . . . ?
C15 C14 C5 C4 -10.2(2) . . . . ?
C15 C14 C5 C6 172.10(14) . . . . ?
C16 C18 C23 N2 -0.47(17) . . . . ?
C16 C18 C23 C22 -179.03(14) . . . . ?
C16 C18 C19 C20 176.38(16) . . . . ?
C16 C15 C14 C13 56.7(2) . . . . ?
C16 C15 C14 C5 -123.68(16) . . . . ?
C16 C15 C1 C3 143.99(15) . . . . ?
C16 C15 C1 C2 -93.06(17) . . . . ?
C17 N2 C23 C18 -3.75(18) . . . . ?
C17 N2 C23 C22 174.74(15) . . . . ?
C23 N2 C17 O1 -173.43(14) . . . . ?
C23 N2 C17 C16 6.20(17) . . . . ?
C23 C18 C16 C15 -177.91(16) . . . . ?
C23 C18 C16 C17 4.00(16) . . . . ?
C23 C18 C19 C20 1.9(2) . . . . ?
C14 C15 C16 C18 3.6(3) . . . . ?
C14 C15 C16 C17 -178.60(14) . . . . ?
C14 C15 C1 C3 -31.52(18) . . . . ?
C14 C15 C1 C2 91.43(15) . . . . ?
C14 C13 C12 C11 -179.69(16) . . . . ?
C14 C13 C8 C7 -1.6(2) . . . . ?
C14 C13 C8 C9 178.52(15) . . . . ?
C14 C5 C6 C7 2.9(3) . . . . ?
C19 C18 C16 C15 7.1(3) . . . . ?
C19 C18 C16 C17 -170.95(17) . . . . ?
C19 C18 C23 N2 175.44(14) . . . . ?
C19 C18 C23 C22 -3.1(2) . . . . ?
C13 C14 C5 C4 169.43(14) . . . . ?
C13 C14 C5 C6 -8.2(2) . . . . ?
C13 C12 C11 C10 0.5(3) . . . . ?
C13 C8 C7 C6 -3.6(3) . . . . ?
C13 C8 C9 C10 1.9(3) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C24 C21 C20 C19 -178.97(14) . . . . ?
C24 C21 C22 C23 177.82(14) . . . . ?
C3 C4 C5 C14 -45.50(18) . . . . ?
C3 C4 C5 C6 132.08(16) . . . . ?
C1 C15 C16 C18 -171.55(15) . . . . ?
C1 C15 C16 C17 6.2(2) . . . . ?
C1 C15 C14 C13 -127.77(15) . . . . ?
C1 C15 C14 C5 51.88(18) . . . . ?
C1 C3 C4 C5 62.35(17) . . . . ?
C4 C3 C1 C15 -24.11(18) . . . . ?
C4 C3 C1 C2 -146.24(14) . . . . ?
C4 C5 C6 C7 -174.57(16) . . . . ?
C5 C14 C13 C12 -171.49(15) . . . . ?
C5 C14 C13 C8 7.5(2) . . . . ?
C5 C6 C7 C8 3.0(3) . . . . ?
C12 C13 C8 C7 177.41(16) . . . . ?
C12 C13 C8 C9 -2.4(2) . . . . ?
C12 C11 C10 C9 -1.1(3) . . . . ?
C22 C21 C20 C19 -1.4(2) . . . . ?
C8 C13 C12 C11 1.3(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C7 C8 C9 C10 -177.98(19) . . . . ?
C9 C8 C7 C6 176.28(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 -0.864 0.500 194.3 20.3 ?
2 0.500 -0.270 1.000 194.3 20.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_drp173_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2143239'
loop_
_audit_author_name
_audit_author_address
'Daisy Pooler'
;Rijksuniversiteit Groningen
Netherlands
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-08-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N2 O'
_chemical_formula_sum            'C30 H22 N2 O'
_chemical_formula_weight         426.49
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   20.5250(6)
_cell_length_b                   7.5707(2)
_cell_length_c                   28.6634(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.0020(10)
_cell_angle_gamma                90
_cell_volume                     4429.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0723 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.9279.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.129
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            42392
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.126
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3896
_reflns_number_total             4167
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.046
_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)+(0.0336P)²+4.1786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H2)
2.b Secondary CH2 refined with riding coordinates:
 C2(H4A,H4B), C1(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H19), C10(H12), C18(H20), C24(H26), C27(H29), C20(H22), C23(H25), C9(H11),
  C19(H21), C26(H28), C7(H9), C8(H10), C5(H7), C4(H6)
2.d Idealised Me refined as rotating group:
 C28(H1A,H1B,H1C)
;
_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
O1 O 0.46957(4) 0.23790(11) 0.41966(3) 0.02451(19) Uani 1 1 d . . . . .
N2 N 0.35928(4) 0.22997(13) 0.43019(3) 0.0198(2) Uani 1 1 d . . . . .
N1 N 0.36400(6) 1.02040(15) 0.54135(4) 0.0347(3) Uani 1 1 d . . . . .
C18 C 0.32414(5) 0.00195(14) 0.38094(4) 0.0179(2) Uani 1 1 d . . . . .
C19 C 0.27891(5) -0.12266(15) 0.36203(4) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.291506 -0.210318 0.341020 0.023 Uiso 1 1 calc R U . . .
C13 C 0.36926(5) -0.14176(15) 0.27593(4) 0.0189(2) Uani 1 1 d . . . . .
C12 C 0.34415(5) 0.03230(15) 0.26881(4) 0.0204(2) Uani 1 1 d . . . . .
H12 H 0.357412 0.122005 0.290965 0.024 Uiso 1 1 calc R U . . .
C23 C 0.30446(5) 0.12786(15) 0.41266(4) 0.0186(2) Uani 1 1 d . . . . .
C14 C 0.41355(5) -0.19163(15) 0.31571(4) 0.0192(2) Uani 1 1 d . . . . .
C17 C 0.41580(5) 0.16950(15) 0.41157(4) 0.0194(2) Uani 1 1 d . . . . .
C16 C 0.39492(5) 0.02213(15) 0.37884(4) 0.0184(2) Uani 1 1 d . . . . .
C15 C 0.43660(5) -0.06809(14) 0.35378(4) 0.0187(2) Uani 1 1 d . . . . .
C24 C 0.35837(5) 0.39078(15) 0.45556(4) 0.0197(2) Uani 1 1 d . . . . .
C27 C 0.36295(6) 0.71551(15) 0.50044(4) 0.0212(2) Uani 1 1 d . . . . .
C20 C 0.21498(5) -0.11740(15) 0.37425(4) 0.0210(2) Uani 1 1 d . . . . .
H20 H 0.183808 -0.201570 0.361354 0.025 Uiso 1 1 calc R U . . .
C26 C 0.31151(6) 0.67684(15) 0.46639(4) 0.0216(2) Uani 1 1 d . . . . .
H26 H 0.277866 0.761310 0.458719 0.026 Uiso 1 1 calc R U . . .
C29 C 0.40894(5) 0.42736(16) 0.49083(4) 0.0210(2) Uani 1 1 d . . . . .
H29 H 0.441267 0.340432 0.499672 0.025 Uiso 1 1 calc R U . . .
C22 C 0.24114(5) 0.13435(15) 0.42538(4) 0.0208(2) Uani 1 1 d . . . . .
H22 H 0.228647 0.219927 0.446996 0.025 Uiso 1 1 calc R U . . .
C25 C 0.30944(6) 0.51534(15) 0.44374(4) 0.0212(2) Uani 1 1 d . . . . .
H25 H 0.274717 0.489369 0.420168 0.025 Uiso 1 1 calc R U . . .
C11 C 0.30116(6) 0.07261(16) 0.23051(4) 0.0230(2) Uani 1 1 d . . . . .
H11 H 0.284878 0.189664 0.226425 0.028 Uiso 1 1 calc R U . . .
C8 C 0.35003(6) -0.27170(16) 0.24136(4) 0.0219(2) Uani 1 1 d . . . . .
C21 C 0.19651(5) 0.01016(16) 0.40518(4) 0.0217(2) Uani 1 1 d . . . . .
H21 H 0.152538 0.012859 0.412720 0.026 Uiso 1 1 calc R U . . .
C28 C 0.41182(5) 0.59014(16) 0.51281(4) 0.0218(2) Uani 1 1 d . . . . .
H28 H 0.446754 0.616712 0.536172 0.026 Uiso 1 1 calc R U . . .
C00O C 0.36446(6) 0.88564(16) 0.52351(4) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.51061(5) -0.05934(15) 0.36433(4) 0.0226(2) Uani 1 1 d . . . . .
H2 H 0.521239 -0.014682 0.397074 0.027 Uiso 1 1 calc R U . . .
C9 C 0.30509(6) -0.22557(17) 0.20224(4) 0.0252(3) Uani 1 1 d . . . . .
H9 H 0.291702 -0.312542 0.179336 0.030 Uiso 1 1 calc R U . . .
C10 C 0.28083(6) -0.05815(17) 0.19705(4) 0.0259(3) Uani 1 1 d . . . . .
H10 H 0.250266 -0.029649 0.170929 0.031 Uiso 1 1 calc R U . . .
C5 C 0.43996(6) -0.36027(16) 0.31904(4) 0.0241(3) Uani 1 1 d . . . . .
C7 C 0.37618(6) -0.44494(16) 0.24691(4) 0.0274(3) Uani 1 1 d . . . . .
H7 H 0.362778 -0.532928 0.224290 0.033 Uiso 1 1 calc R U . . .
C6 C 0.42037(6) -0.48715(16) 0.28433(5) 0.0287(3) Uani 1 1 d . . . . .
H6 H 0.438060 -0.603111 0.286968 0.034 Uiso 1 1 calc R U . . .
C4 C 0.49115(6) -0.39414(17) 0.35974(5) 0.0318(3) Uani 1 1 d . . . . .
H4A H 0.512791 -0.509211 0.355739 0.038 Uiso 1 1 calc R U . . .
H4B H 0.470593 -0.397076 0.389477 0.038 Uiso 1 1 calc R U . . .
C3 C 0.54113(6) -0.24519(17) 0.36089(5) 0.0336(3) Uani 1 1 d . . . . .
H3A H 0.563859 -0.251135 0.332126 0.040 Uiso 1 1 calc R U . . .
H3B H 0.574347 -0.262966 0.388104 0.040 Uiso 1 1 calc R U . . .
C1 C 0.53977(6) 0.06848(19) 0.33061(5) 0.0360(3) Uani 1 1 d . . . . .
H1A H 0.527204 0.030958 0.298198 0.054 Uiso 1 1 calc R U . . .
H1B H 0.587631 0.068332 0.336898 0.054 Uiso 1 1 calc R U . . .
H1C H 0.523121 0.187879 0.335187 0.054 Uiso 1 1 calc R U . . .


_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 C17 1.2191(14) . ?
N2 C23 1.4133(14) . ?
N2 C17 1.4034(14) . ?
N2 C24 1.4193(14) . ?
N1 C00O 1.1417(17) . ?
C18 C19 1.3930(16) . ?
C18 C23 1.4056(15) . ?
C18 C16 1.4682(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3936(16) . ?
C13 C12 1.4219(16) . ?
C13 C14 1.4325(15) . ?
C13 C8 1.4225(16) . ?
C12 H12 0.9500 . ?
C12 C11 1.3690(16) . ?
C23 C22 1.3870(16) . ?
C14 C15 1.4769(15) . ?
C14 C5 1.3864(16) . ?
C17 C16 1.4916(15) . ?
C16 C15 1.3575(16) . ?
C15 C2 1.5190(15) . ?
C24 C29 1.3987(16) . ?
C24 C25 1.3934(16) . ?
C27 C26 1.3919(16) . ?
C27 C28 1.3994(16) . ?
C27 C00O 1.4467(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3902(17) . ?
C26 H26 0.9500 . ?
C26 C25 1.3829(16) . ?
C29 H29 0.9500 . ?
C29 C28 1.3826(16) . ?
C22 H22 0.9500 . ?
C22 C21 1.3956(17) . ?
C25 H25 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.4107(17) . ?
C8 C9 1.4191(17) . ?
C8 C7 1.4198(17) . ?
C21 H21 0.9500 . ?
C28 H28 0.9500 . ?
C2 H2 1.0000 . ?
C2 C3 1.5475(16) . ?
C2 C1 1.5328(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3642(18) . ?
C10 H10 0.9500 . ?
C5 C6 1.4108(17) . ?
C5 C4 1.5081(17) . ?
C7 H7 0.9500 . ?
C7 C6 1.3681(18) . ?
C6 H6 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5225(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C23 N2 C24 126.77(9) . . ?
C17 N2 C23 110.21(9) . . ?
C17 N2 C24 122.02(9) . . ?
C19 C18 C23 119.08(10) . . ?
C19 C18 C16 132.58(10) . . ?
C23 C18 C16 107.96(9) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.32(10) . . ?
C20 C19 H19 120.3 . . ?
C12 C13 C14 123.29(10) . . ?
C12 C13 C8 118.09(10) . . ?
C8 C13 C14 118.61(10) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 121.01(11) . . ?
C11 C12 H12 119.5 . . ?
C18 C23 N2 109.20(9) . . ?
C22 C23 N2 128.33(10) . . ?
C22 C23 C18 122.32(10) . . ?
C13 C14 C15 123.28(10) . . ?
C5 C14 C13 120.57(10) . . ?
C5 C14 C15 116.07(10) . . ?
O1 C17 N2 123.85(10) . . ?
O1 C17 C16 129.22(10) . . ?
N2 C17 C16 106.77(9) . . ?
C18 C16 C17 105.82(9) . . ?
C15 C16 C18 130.56(10) . . ?
C15 C16 C17 123.62(10) . . ?
C14 C15 C2 114.27(9) . . ?
C16 C15 C14 122.60(10) . . ?
C16 C15 C2 123.03(10) . . ?
C29 C24 N2 119.45(10) . . ?
C25 C24 N2 120.25(10) . . ?
C25 C24 C29 120.21(10) . . ?
C26 C27 C28 120.40(11) . . ?
C26 C27 C00O 119.09(10) . . ?
C28 C27 C00O 120.50(10) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.45(11) . . ?
C21 C20 H20 119.8 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 119.93(11) . . ?
C25 C26 H26 120.0 . . ?
C24 C29 H29 120.0 . . ?
C28 C29 C24 119.94(10) . . ?
C28 C29 H29 120.0 . . ?
C23 C22 H22 121.3 . . ?
C23 C22 C21 117.36(10) . . ?
C21 C22 H22 121.3 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.88(10) . . ?
C26 C25 H25 120.1 . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.58(11) . . ?
C10 C11 H11 119.7 . . ?
C9 C8 C13 119.36(11) . . ?
C9 C8 C7 121.52(11) . . ?
C7 C8 C13 119.13(11) . . ?
C20 C21 C22 121.45(10) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.59(10) . . ?
C29 C28 H28 120.2 . . ?
N1 C00O C27 178.26(13) . . ?
C15 C2 H2 108.5 . . ?
C15 C2 C3 110.53(10) . . ?
C15 C2 C1 110.51(10) . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 110.28(10) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.97(11) . . ?
C10 C9 H9 119.5 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 119.95(11) . . ?
C9 C10 H10 120.0 . . ?
C14 C5 C6 119.86(11) . . ?
C14 C5 C4 116.46(10) . . ?
C6 C5 C4 123.63(11) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.03(11) . . ?
C6 C7 H7 119.5 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.70(11) . . ?
C7 C6 H6 119.7 . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C5 C4 C3 107.71(11) . . ?
H4A C4 H4B 108.5 . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 C2 113.49(10) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
O1 C17 C16 C18 -176.38(11) . . . . ?
O1 C17 C16 C15 3.89(19) . . . . ?
N2 C23 C22 C21 -175.51(10) . . . . ?
N2 C17 C16 C18 -1.01(11) . . . . ?
N2 C17 C16 C15 179.27(10) . . . . ?
N2 C24 C29 C28 174.08(10) . . . . ?
N2 C24 C25 C26 -175.40(10) . . . . ?
C18 C19 C20 C21 -0.34(16) . . . . ?
C18 C23 C22 C21 -0.30(16) . . . . ?
C18 C16 C15 C14 11.23(18) . . . . ?
C18 C16 C15 C2 -164.96(11) . . . . ?
C19 C18 C23 N2 175.05(9) . . . . ?
C19 C18 C23 C22 -0.97(16) . . . . ?
C19 C18 C16 C17 -172.81(11) . . . . ?
C19 C18 C16 C15 6.9(2) . . . . ?
C19 C20 C21 C22 -0.98(17) . . . . ?
C13 C12 C11 C10 -0.13(17) . . . . ?
C13 C14 C15 C16 56.41(16) . . . . ?
C13 C14 C15 C2 -127.09(11) . . . . ?
C13 C14 C5 C6 -3.53(17) . . . . ?
C13 C14 C5 C4 174.07(10) . . . . ?
C13 C8 C9 C10 0.86(17) . . . . ?
C13 C8 C7 C6 -1.35(18) . . . . ?
C12 C13 C14 C15 1.21(17) . . . . ?
C12 C13 C14 C5 -175.41(11) . . . . ?
C12 C13 C8 C9 -2.26(16) . . . . ?
C12 C13 C8 C7 177.91(10) . . . . ?
C12 C11 C10 C9 -1.34(17) . . . . ?
C23 N2 C17 O1 177.47(10) . . . . ?
C23 N2 C17 C16 1.78(12) . . . . ?
C23 N2 C24 C29 145.34(11) . . . . ?
C23 N2 C24 C25 -38.10(16) . . . . ?
C23 C18 C19 C20 1.28(16) . . . . ?
C23 C18 C16 C17 -0.11(12) . . . . ?
C23 C18 C16 C15 179.59(11) . . . . ?
C23 C22 C21 C20 1.28(16) . . . . ?
C14 C13 C12 C11 -179.04(10) . . . . ?
C14 C13 C8 C9 178.65(10) . . . . ?
C14 C13 C8 C7 -1.18(16) . . . . ?
C14 C15 C2 C3 -38.68(14) . . . . ?
C14 C15 C2 C1 83.67(12) . . . . ?
C14 C5 C6 C7 0.95(19) . . . . ?
C14 C5 C4 C3 -49.09(15) . . . . ?
C17 N2 C23 C18 -1.90(12) . . . . ?
C17 N2 C23 C22 173.81(11) . . . . ?
C17 N2 C24 C29 -47.18(15) . . . . ?
C17 N2 C24 C25 129.38(11) . . . . ?
C17 C16 C15 C14 -169.11(10) . . . . ?
C17 C16 C15 C2 14.69(17) . . . . ?
C16 C18 C19 C20 173.33(11) . . . . ?
C16 C18 C23 N2 1.20(12) . . . . ?
C16 C18 C23 C22 -174.82(10) . . . . ?
C16 C15 C2 C3 137.80(12) . . . . ?
C16 C15 C2 C1 -99.84(13) . . . . ?
C15 C14 C5 C6 179.60(11) . . . . ?
C15 C14 C5 C4 -2.79(15) . . . . ?
C15 C2 C3 C4 -13.86(15) . . . . ?
C24 N2 C23 C18 166.80(10) . . . . ?
C24 N2 C23 C22 -17.49(18) . . . . ?
C24 N2 C17 O1 8.14(17) . . . . ?
C24 N2 C17 C16 -167.55(9) . . . . ?
C24 C29 C28 C27 1.76(17) . . . . ?
C27 C26 C25 C24 0.92(17) . . . . ?
C26 C27 C28 C29 0.29(17) . . . . ?
C29 C24 C25 C26 1.13(17) . . . . ?
C25 C24 C29 C28 -2.48(17) . . . . ?
C8 C13 C12 C11 1.91(16) . . . . ?
C8 C13 C14 C15 -179.75(10) . . . . ?
C8 C13 C14 C5 3.62(16) . . . . ?
C8 C9 C10 C11 0.95(18) . . . . ?
C8 C7 C6 C5 1.51(19) . . . . ?
C28 C27 C26 C25 -1.65(17) . . . . ?
C00O C27 C26 C25 179.59(11) . . . . ?
C00O C27 C28 C29 179.04(11) . . . . ?
C9 C8 C7 C6 178.82(11) . . . . ?
C5 C14 C15 C16 -126.82(12) . . . . ?
C5 C14 C15 C2 49.68(14) . . . . ?
C5 C4 C3 C2 56.64(15) . . . . ?
C7 C8 C9 C10 -179.31(11) . . . . ?
C6 C5 C4 C3 128.41(13) . . . . ?
C4 C5 C6 C7 -176.47(12) . . . . ?
C1 C2 C3 C4 -136.34(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
