# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_BreitPZ_R_122_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1950247'
loop_
_audit_author_name
_audit_author_address
'Daniel Kratzert'
;University of Freiburg
Germany
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2021-04-22 downloaded from the CCDC.
;
_diffrn_source_type              'Incoatec I\ms'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 HPAD
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_monochromator  'mirror optics'
_exptl_special_details           ?
_exptl_crystal_recrystallization_method 'from chloroform by evaporation'
_audit_creation_method           'FinalCif by Daniel Kratzert, Freiburg 2019'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N2 O'
_chemical_formula_sum            'C24 H30 N2 O'
_chemical_formula_weight         362.50

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'

_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'
_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.
;

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                   9.1380(11)
_cell_length_b                   13.8136(18)
_cell_length_c                   15.8299(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1998.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0
_cell_measurement_reflns_used    6325
_cell_measurement_theta_min      2.575
_cell_measurement_theta_max      25.422
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7082
_exptl_absorpt_correction_T_max  0.7427
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            53072
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.957
_diffrn_reflns_theta_max         26.803
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4271
_reflns_number_gt                3531
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000
_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.
;
_computing_data_collection       'Bruker BIS V6.2.11/2019-03-14'
_computing_cell_refinement       'SAINT V8.38A'
_computing_data_reduction        'SAINT V8.38A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.3422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4271
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5124(2) 0.85334(12) 0.41435(11) 0.0204(4) Uani 1 1 d . . . . .
N1 N 0.3887(2) 0.62361(15) 0.34405(12) 0.0162(5) Uani 1 1 d . . . . .
C1 C 0.4460(3) 0.71970(18) 0.31825(15) 0.0152(5) Uani 1 1 d . . . . .
N2 N 0.3975(2) 0.71742(15) 0.46348(12) 0.0162(5) Uani 1 1 d . . . . .
C2 C 0.3331(3) 0.77670(18) 0.26566(15) 0.0166(5) Uani 1 1 d . . . . .
C3 C 0.2042(3) 0.8138(2) 0.31513(16) 0.0220(6) Uani 1 1 d . . . . .
H3A H 0.119768 0.820921 0.277448 0.033 Uiso 1 1 calc R U . . .
H3B H 0.228520 0.876858 0.339870 0.033 Uiso 1 1 calc R U . . .
H3C H 0.180320 0.767966 0.360292 0.033 Uiso 1 1 calc R U . . .
C004 C 0.4600(3) 0.77257(18) 0.40347(16) 0.0166(6) Uani 1 1 d . . . . .
C4 C 0.3457(3) 0.78406(18) 0.18152(15) 0.0169(5) Uani 1 1 d . . . . .
H4 H 0.431934 0.757006 0.157766 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2426(3) 0.82885(18) 0.12077(15) 0.0157(5) Uani 1 1 d . . . . .
C9 C 0.1402(3) 0.82717(19) -0.02071(16) 0.0231(6) Uani 1 1 d . . . . .
H9 H 0.132705 0.797399 -0.074633 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0583(3) 0.9090(2) -0.00294(17) 0.0257(6) Uani 1 1 d . . . . .
H8 H -0.004262 0.936103 -0.044605 0.031 Uiso 1 1 calc R U . . .
C7 C 0.0688(3) 0.9508(2) 0.07631(17) 0.0241(6) Uani 1 1 d . . . . .
H7 H 0.012957 1.006941 0.088968 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1598(3) 0.91162(18) 0.13734(16) 0.0190(6) Uani 1 1 d . . . . .
H6 H 0.165938 0.941515 0.191271 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2332(3) 0.78838(19) 0.03975(15) 0.0200(6) Uani 1 1 d . . . . .
H10 H 0.291413 0.733596 0.026026 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5959(3) 0.71192(19) 0.27506(14) 0.0166(5) Uani 1 1 d . . . . .
C12 C 0.6731(3) 0.79632(19) 0.25633(14) 0.0177(5) Uani 1 1 d . . . . .
H12 H 0.631321 0.857496 0.269352 0.021 Uiso 1 1 calc R U . . .
C13 C 0.8105(3) 0.7920(2) 0.21886(16) 0.0215(6) Uani 1 1 d . . . . .
H13 H 0.862702 0.850018 0.207405 0.026 Uiso 1 1 calc R U . . .
C14 C 0.8717(3) 0.7030(2) 0.19809(15) 0.0238(6) Uani 1 1 d . . . . .
H14 H 0.965287 0.699770 0.172081 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7947(3) 0.6193(2) 0.21575(17) 0.0248(6) Uani 1 1 d . . . . .
H15 H 0.835875 0.558299 0.201539 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6578(3) 0.62321(19) 0.25407(15) 0.0208(6) Uani 1 1 d . . . . .
H16 H 0.606385 0.564995 0.265928 0.025 Uiso 1 1 calc R U . . .
C17 C 0.2818(3) 0.5794(2) 0.28746(17) 0.0249(6) Uani 1 1 d . . . . .
H17A H 0.257962 0.514201 0.307606 0.037 Uiso 1 1 calc R U . . .
H17B H 0.322752 0.575434 0.230364 0.037 Uiso 1 1 calc R U . . .
H17C H 0.192708 0.618937 0.286434 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3490(3) 0.62224(17) 0.43447(14) 0.0159(5) Uani 1 1 d . . . . .
H18 H 0.240195 0.617566 0.440090 0.019 Uiso 1 1 calc R U . . .
C19 C 0.3658(3) 0.75702(19) 0.54704(15) 0.0204(6) Uani 1 1 d . . . . .
H19A H 0.270980 0.732574 0.566643 0.031 Uiso 1 1 calc R U . . .
H19B H 0.362495 0.827836 0.543856 0.031 Uiso 1 1 calc R U . . .
H19C H 0.442492 0.737211 0.586681 0.031 Uiso 1 1 calc R U . . .
C20 C 0.4217(3) 0.53753(18) 0.48371(15) 0.0181(6) Uani 1 1 d . . . . .
C21 C 0.5872(3) 0.55282(19) 0.48789(16) 0.0205(6) Uani 1 1 d . . . . .
H21A H 0.633088 0.496952 0.515374 0.031 Uiso 1 1 calc R U . . .
H21B H 0.608511 0.611511 0.520440 0.031 Uiso 1 1 calc R U . . .
H21C H 0.626251 0.559816 0.430548 0.031 Uiso 1 1 calc R U . . .
C22 C 0.3916(3) 0.44183(19) 0.43823(17) 0.0240(6) Uani 1 1 d . . . . .
H22A H 0.436097 0.388519 0.469997 0.036 Uiso 1 1 calc R U . . .
H22B H 0.433792 0.444170 0.381339 0.036 Uiso 1 1 calc R U . . .
H22C H 0.285756 0.431522 0.434215 0.036 Uiso 1 1 calc R U . . .
C23 C 0.3579(3) 0.5288(2) 0.57344(16) 0.0249(6) Uani 1 1 d . . . . .
H23A H 0.387122 0.466641 0.598125 0.037 Uiso 1 1 calc R U . . .
H23B H 0.250889 0.532325 0.570731 0.037 Uiso 1 1 calc R U . . .
H23C H 0.395082 0.581753 0.608568 0.037 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 C004 1.226(3) . ?
N1 C17 1.460(3) . ?
N1 C18 1.477(3) . ?
N1 C1 1.484(3) . ?
C1 C11 1.535(3) . ?
C1 C004 1.539(3) . ?
C1 C2 1.542(3) . ?
N2 C004 1.345(3) . ?
N2 C19 1.460(3) . ?
N2 C18 1.462(3) . ?
C2 C4 1.341(3) . ?
C2 C3 1.505(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.481(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(3) . ?
C5 C10 1.402(3) . ?
C9 C8 1.384(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C8 C7 1.384(4) . ?
C8 H8 0.9500 . ?
C7 C6 1.385(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.390(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.555(3) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.529(3) . ?
C20 C22 1.530(4) . ?
C20 C23 1.540(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C17 N1 C18 115.1(2) . . ?
C17 N1 C1 116.18(19) . . ?
C18 N1 C1 111.40(19) . . ?
N1 C1 C11 112.0(2) . . ?
N1 C1 C004 102.27(18) . . ?
C11 C1 C004 110.42(19) . . ?
N1 C1 C2 111.70(19) . . ?
C11 C1 C2 113.11(19) . . ?
C004 C1 C2 106.67(19) . . ?
C004 N2 C19 120.8(2) . . ?
C004 N2 C18 114.61(19) . . ?
C19 N2 C18 124.1(2) . . ?
C4 C2 C3 124.0(2) . . ?
C4 C2 C1 121.2(2) . . ?
C3 C2 C1 114.6(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C004 N2 125.6(2) . . ?
O1 C004 C1 126.0(2) . . ?
N2 C004 C1 108.3(2) . . ?
C2 C4 C5 128.5(2) . . ?
C2 C4 H4 115.8 . . ?
C5 C4 H4 115.8 . . ?
C6 C5 C10 117.7(2) . . ?
C6 C5 C4 124.4(2) . . ?
C10 C5 C4 117.8(2) . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C9 C10 C5 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C16 C11 C12 118.7(2) . . ?
C16 C11 C1 122.1(2) . . ?
C12 C11 C1 119.2(2) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 N1 102.60(18) . . ?
N2 C18 C20 112.94(19) . . ?
N1 C18 C20 113.0(2) . . ?
N2 C18 H18 109.4 . . ?
N1 C18 H18 109.4 . . ?
C20 C18 H18 109.4 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 108.5(2) . . ?
C21 C20 C23 110.2(2) . . ?
C22 C20 C23 107.3(2) . . ?
C21 C20 C18 109.9(2) . . ?
C22 C20 C18 109.7(2) . . ?
C23 C20 C18 111.1(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
