# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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_nzr1342
_database_code_depnum_ccdc_archive 'CCDC 2095888'
loop_
_audit_author_name
_audit_author_address
'Elizaveta Melnikova'
;INEOS
Russia
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;
_audit_creation_date             2021-07-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H23 N O2'
_chemical_formula_sum            'C17 H23 N O2'
_chemical_formula_weight         273.36
_chemical_absolute_configuration ?
_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 0.0033 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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.524(8)
_cell_length_b                   8.428(10)
_cell_length_c                   13.854(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.68(3)
_cell_angle_gamma                90
_cell_volume                     754.9(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6532
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6931
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0495 before and 0.0416 after correction.
The Ratio of minimum to maximum transmission is 0.9290.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8149
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.836
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3924
_reflns_number_total             4295
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.033
_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)+(0.0610P)²+0.0398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1040
_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:
 C4(H4), C3(H3), C8(H8), C12(H12), C10(H10), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C17(H17A,H17B), C15(H15A,H15B), C14(H14A,H14B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.5696(2) 0.63290(15) 0.19147(10) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.0707(2) 0.28957(17) 0.26599(11) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.2881(2) 0.49095(17) 0.22935(10) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.4890(2) 0.50680(19) 0.20639(12) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.2364(3) 0.3326(2) 0.24467(12) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.5859(3) 0.3433(2) 0.20357(12) 0.0160(3) Uani 1 1 d . . . . .
H4 H 0.7162 0.3339 0.2502 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4169(3) 0.2274(2) 0.22856(12) 0.0161(3) Uani 1 1 d . . . . .
H3 H 0.4657 0.1618 0.2873 0.019 Uiso 1 1 calc R U . . .
C8 C 0.3714(3) 0.1227(2) 0.13393(12) 0.0193(3) Uani 1 1 d . . . . .
H8 H 0.2394 0.0609 0.1263 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7138(3) 0.1272(2) 0.10946(13) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.8525 0.1004 0.1025 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2144(3) 0.7436(2) 0.31397(12) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.3276 0.8084 0.2916 0.022 Uiso 1 1 calc R U . . .
C7 C 0.5691(3) 0.0275(2) 0.13141(13) 0.0223(4) Uani 1 1 d . . . . .
H7 H 0.5859 -0.0831 0.1434 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1386(3) 0.6222(2) 0.23351(12) 0.0179(3) Uani 1 1 d . . . . .
H10 H 0.0087 0.5741 0.2513 0.021 Uiso 1 1 calc R U . . .
C11 C 0.0849(3) 0.6944(3) 0.13169(14) 0.0261(4) Uani 1 1 d . . . . .
H11A H 0.2091 0.7423 0.1112 0.039 Uiso 1 1 calc R U . . .
H11B H -0.0215 0.7761 0.1333 0.039 Uiso 1 1 calc R U . . .
H11C H 0.0329 0.6111 0.0855 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3946(3) 0.2472(2) 0.05412(13) 0.0212(4) Uani 1 1 d . . . . .
H9A H 0.3859 0.2003 -0.0118 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2961 0.3366 0.0542 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6177(3) 0.2922(2) 0.09734(13) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.6899 0.3704 0.0593 0.024 Uiso 1 1 calc R U . . .
C13 C 0.0373(4) 0.8551(3) 0.33106(15) 0.0312(5) Uani 1 1 d . . . . .
H13A H -0.0072 0.9154 0.2706 0.037 Uiso 1 1 calc R U . . .
H13B H -0.0818 0.7909 0.3457 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2995(4) 0.6618(2) 0.40935(15) 0.0341(5) Uani 1 1 d . . . . .
H17A H 0.4221 0.5980 0.3991 0.041 Uiso 1 1 calc R U . . .
H17B H 0.1934 0.5884 0.4285 0.041 Uiso 1 1 calc R U . . .
C15 C 0.1810(4) 0.8879(3) 0.50855(16) 0.0374(5) Uani 1 1 d . . . . .
H15A H 0.0700 0.8241 0.5318 0.045 Uiso 1 1 calc R U . . .
H15B H 0.2285 0.9675 0.5592 0.045 Uiso 1 1 calc R U . . .
C14 C 0.0969(4) 0.9718(2) 0.41430(15) 0.0346(5) Uani 1 1 d . . . . .
H14A H 0.2030 1.0459 0.3960 0.042 Uiso 1 1 calc R U . . .
H14B H -0.0261 1.0349 0.4249 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3604(5) 0.7803(4) 0.49206(18) 0.0536(8) Uani 1 1 d . . . . .
H16A H 0.4078 0.7215 0.5528 0.064 Uiso 1 1 calc R U . . .
H16B H 0.4771 0.8461 0.4762 0.064 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 C1 1.216(2) . ?
O2 C2 1.214(2) . ?
N1 C1 1.396(3) . ?
N1 C2 1.399(3) . ?
N1 C10 1.481(3) . ?
C1 C4 1.519(3) . ?
C2 C3 1.515(3) . ?
C4 H4 1.0000 . ?
C4 C3 1.546(3) . ?
C4 C5 1.573(3) . ?
C3 H3 1.0000 . ?
C3 C8 1.575(3) . ?
C8 H8 1.0000 . ?
C8 C7 1.523(3) . ?
C8 C9 1.546(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.329(3) . ?
C6 C5 1.526(3) . ?
C12 H12 1.0000 . ?
C12 C10 1.545(3) . ?
C12 C13 1.532(3) . ?
C12 C17 1.528(3) . ?
C7 H7 0.9500 . ?
C10 H10 1.0000 . ?
C10 C11 1.533(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C5 1.546(3) . ?
C5 H5 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.526(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.532(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.521(3) . ?
C15 C16 1.522(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C1 N1 C2 112.23(14) . . ?
C1 N1 C10 125.49(15) . . ?
C2 N1 C10 122.23(16) . . ?
O1 C1 N1 124.27(15) . . ?
O1 C1 C4 126.73(16) . . ?
N1 C1 C4 109.00(14) . . ?
O2 C2 N1 124.23(16) . . ?
O2 C2 C3 126.59(17) . . ?
N1 C2 C3 109.18(15) . . ?
C1 C4 H4 112.1 . . ?
C1 C4 C3 104.84(15) . . ?
C1 C4 C5 112.29(14) . . ?
C3 C4 H4 112.1 . . ?
C3 C4 C5 102.95(14) . . ?
C5 C4 H4 112.1 . . ?
C2 C3 C4 104.74(16) . . ?
C2 C3 H3 111.9 . . ?
C2 C3 C8 112.77(15) . . ?
C4 C3 H3 111.9 . . ?
C4 C3 C8 103.19(14) . . ?
C8 C3 H3 111.9 . . ?
C3 C8 H8 116.3 . . ?
C7 C8 C3 104.37(14) . . ?
C7 C8 H8 116.3 . . ?
C7 C8 C9 100.23(15) . . ?
C9 C8 C3 100.92(16) . . ?
C9 C8 H8 116.3 . . ?
C7 C6 H6 126.0 . . ?
C7 C6 C5 107.93(17) . . ?
C5 C6 H6 126.0 . . ?
C10 C12 H12 108.5 . . ?
C13 C12 H12 108.5 . . ?
C13 C12 C10 110.01(16) . . ?
C17 C12 H12 108.5 . . ?
C17 C12 C10 111.67(17) . . ?
C17 C12 C13 109.72(16) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 C8 107.54(17) . . ?
C6 C7 H7 126.2 . . ?
N1 C10 C12 111.96(15) . . ?
N1 C10 H10 106.9 . . ?
N1 C10 C11 109.36(14) . . ?
C12 C10 H10 106.9 . . ?
C11 C10 C12 114.36(17) . . ?
C11 C10 H10 106.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 113.0 . . ?
C8 C9 H9B 113.0 . . ?
H9A C9 H9B 110.4 . . ?
C5 C9 C8 93.81(14) . . ?
C5 C9 H9A 113.0 . . ?
C5 C9 H9B 113.0 . . ?
C4 C5 H5 116.3 . . ?
C6 C5 C4 104.47(14) . . ?
C6 C5 C9 99.81(15) . . ?
C6 C5 H5 116.3 . . ?
C9 C5 C4 101.19(14) . . ?
C9 C5 H5 116.3 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 113.0(2) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C17 H17A 109.1 . . ?
C12 C17 H17B 109.1 . . ?
C12 C17 C16 112.3(2) . . ?
H17A C17 H17B 107.9 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C14 C15 C16 110.15(19) . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 C13 112.05(19) . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 C17 111.9(2) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?

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
O1 C1 C4 C3 179.59(17) . . . . ?
O1 C1 C4 C5 -69.4(2) . . . . ?
O2 C2 C3 C4 -179.94(17) . . . . ?
O2 C2 C3 C8 68.6(2) . . . . ?
N1 C1 C4 C3 -0.37(17) . . . . ?
N1 C1 C4 C5 110.68(16) . . . . ?
N1 C2 C3 C4 1.11(18) . . . . ?
N1 C2 C3 C8 -110.37(17) . . . . ?
C1 N1 C2 O2 179.59(16) . . . . ?
C1 N1 C2 C3 -1.44(19) . . . . ?
C1 N1 C10 C12 -63.6(2) . . . . ?
C1 N1 C10 C11 64.2(2) . . . . ?
C1 C4 C3 C2 -0.44(17) . . . . ?
C1 C4 C3 C8 117.77(14) . . . . ?
C1 C4 C5 C6 -179.67(14) . . . . ?
C1 C4 C5 C9 -76.34(17) . . . . ?
C2 N1 C1 O1 -178.82(16) . . . . ?
C2 N1 C1 C4 1.13(18) . . . . ?
C2 N1 C10 C12 119.23(18) . . . . ?
C2 N1 C10 C11 -112.96(18) . . . . ?
C2 C3 C8 C7 -179.99(14) . . . . ?
C2 C3 C8 C9 76.36(17) . . . . ?
C4 C3 C8 C7 67.58(17) . . . . ?
C4 C3 C8 C9 -36.08(16) . . . . ?
C3 C4 C5 C6 -67.44(18) . . . . ?
C3 C4 C5 C9 35.89(16) . . . . ?
C3 C8 C7 C6 -71.10(19) . . . . ?
C3 C8 C9 C5 56.87(14) . . . . ?
C8 C9 C5 C4 -56.94(16) . . . . ?
C8 C9 C5 C6 50.08(15) . . . . ?
C12 C13 C14 C15 -54.8(3) . . . . ?
C12 C17 C16 C15 56.1(3) . . . . ?
C7 C8 C9 C5 -50.09(16) . . . . ?
C7 C6 C5 C4 70.68(18) . . . . ?
C7 C6 C5 C9 -33.68(19) . . . . ?
C10 N1 C1 O1 3.8(3) . . . . ?
C10 N1 C1 C4 -176.29(14) . . . . ?
C10 N1 C2 O2 -2.9(3) . . . . ?
C10 N1 C2 C3 176.08(14) . . . . ?
C10 C12 C13 C14 176.28(17) . . . . ?
C10 C12 C17 C16 -175.7(2) . . . . ?
C9 C8 C7 C6 33.07(19) . . . . ?
C5 C4 C3 C2 -118.06(14) . . . . ?
C5 C4 C3 C8 0.15(16) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C13 C12 C10 N1 -167.35(15) . . . . ?
C13 C12 C10 C11 67.6(2) . . . . ?
C13 C12 C17 C16 -53.5(3) . . . . ?
C17 C12 C10 N1 -45.3(2) . . . . ?
C17 C12 C10 C11 -170.37(17) . . . . ?
C17 C12 C13 C14 53.1(2) . . . . ?
C14 C15 C16 C17 -55.4(3) . . . . ?
C16 C15 C14 C13 54.7(3) . . . . ?

_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_NZR1352
_database_code_depnum_ccdc_archive 'CCDC 2095889'
loop_
_audit_author_name
_audit_author_address
'Elizaveta Melnikova'
;INEOS
Russia
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;
_audit_creation_date             2021-07-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_absolute_configuration ad
_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      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                   5.48910(10)
_cell_length_b                   10.9586(3)
_cell_length_c                   24.8426(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1494.35(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    120
_cell_measurement_theta_max      67.53
_cell_measurement_theta_min      3.56
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1286 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.8657.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21265
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.934
_diffrn_reflns_theta_min         3.558
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.64
_diffrn_source_power             0.0285568
_diffrn_source_voltage           44.62
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2628
_reflns_number_total             2704
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.059
_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)+(0.0412P)²+0.2052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0699
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C8(H8), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C7(H7), C17(H17), C19(H19), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.0196(2) 0.32717(10) 0.71193(4) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.6559(2) 0.58964(10) 0.68917(5) 0.0282(3) Uani 1 1 d . . . . .
N1 N 0.3208(2) 0.46352(11) 0.68870(5) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.2043(3) 0.38218(13) 0.72319(6) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.5263(3) 0.51623(14) 0.71177(6) 0.0223(3) Uani 1 1 d . . . . .
C4 C 0.3463(3) 0.37559(14) 0.77518(6) 0.0224(3) Uani 1 1 d . . . . .
H4 H 0.4086 0.2913 0.7822 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2032(3) 0.42729(14) 0.82454(6) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.0358 0.3939 0.8304 0.028 Uiso 1 1 calc R U . . .
C11 C 0.1625(3) 0.63029(14) 0.63090(6) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.0472 0.6533 0.6598 0.029 Uiso 1 1 calc R U . . .
H11B H 0.3115 0.6804 0.6348 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3973(3) 0.45462(14) 0.59039(6) 0.0217(3) Uani 1 1 d . . . . .
C10 C 0.2261(3) 0.49477(14) 0.63510(6) 0.0205(3) Uani 1 1 d . . . . .
H10 H 0.0708 0.4483 0.6303 0.025 Uiso 1 1 calc R U . . .
C16 C 0.5571(3) 0.35716(15) 0.59716(7) 0.0272(4) Uani 1 1 d . . . . .
H16 H 0.5618 0.3158 0.6308 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3895(3) 0.51517(16) 0.54084(6) 0.0272(4) Uani 1 1 d . . . . .
C8 C 0.5023(3) 0.56481(17) 0.81258(7) 0.0315(4) Uani 1 1 d . . . . .
H8 H 0.5834 0.6459 0.8080 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2205(3) 0.56507(15) 0.81307(7) 0.0281(4) Uani 1 1 d . . . . .
H9A H 0.1512 0.6158 0.8423 0.034 Uiso 1 1 calc R U . . .
H9B H 0.1489 0.5883 0.7780 0.034 Uiso 1 1 calc R U . . .
C12 C 0.0471(3) 0.65200(17) 0.57609(7) 0.0314(4) Uani 1 1 d . . . . .
H12A H -0.0078 0.7378 0.5735 0.038 Uiso 1 1 calc R U . . .
H12B H -0.0972 0.5987 0.5719 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5551(3) 0.46737(16) 0.76801(6) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.7176 0.4279 0.7732 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3777(3) 0.41714(17) 0.87147(7) 0.0307(4) Uani 1 1 d . . . . .
H6 H 0.3641 0.3616 0.9007 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5514(3) 0.49853(19) 0.86492(7) 0.0356(4) Uani 1 1 d . . . . .
H7 H 0.6837 0.5130 0.8887 0.043 Uiso 1 1 calc R U . . .
C17 C 0.7091(4) 0.31925(17) 0.55606(7) 0.0342(4) Uani 1 1 d . . . . .
H17 H 0.8184 0.2532 0.5616 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5429(4) 0.47524(18) 0.49981(7) 0.0347(4) Uani 1 1 d . . . . .
H19 H 0.5390 0.5159 0.4660 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7007(4) 0.37819(18) 0.50678(7) 0.0366(4) Uani 1 1 d . . . . .
H18 H 0.8025 0.3522 0.4780 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2292(4) 0.62522(19) 0.53120(7) 0.0377(4) Uani 1 1 d . . . . .
H13A H 0.1381 0.6127 0.4972 0.045 Uiso 1 1 calc R U . . .
H13B H 0.3347 0.6977 0.5263 0.045 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 C1 1.213(2) . ?
O2 C2 1.2119(19) . ?
N1 C1 1.392(2) . ?
N1 C2 1.391(2) . ?
N1 C10 1.4700(19) . ?
C1 C4 1.510(2) . ?
C2 C3 1.505(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.563(2) . ?
C4 C3 1.535(2) . ?
C5 H5 1.0000 . ?
C5 C9 1.540(2) . ?
C5 C6 1.513(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.529(2) . ?
C11 C12 1.520(2) . ?
C15 C10 1.520(2) . ?
C15 C16 1.392(2) . ?
C15 C14 1.399(2) . ?
C10 H10 1.0000 . ?
C16 H16 0.9500 . ?
C16 C17 1.382(2) . ?
C14 C19 1.393(2) . ?
C14 C13 1.512(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.547(3) . ?
C8 C3 1.565(2) . ?
C8 C7 1.514(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.526(3) . ?
C3 H3 1.0000 . ?
C6 H6 0.9500 . ?
C6 C7 1.316(3) . ?
C7 H7 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.383(3) . ?
C18 H18 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C1 N1 C10 122.96(13) . . ?
C2 N1 C1 112.64(13) . . ?
C2 N1 C10 124.30(13) . . ?
O1 C1 N1 124.10(14) . . ?
O1 C1 C4 127.24(14) . . ?
N1 C1 C4 108.66(13) . . ?
O2 C2 N1 124.12(15) . . ?
O2 C2 C3 127.22(15) . . ?
N1 C2 C3 108.66(13) . . ?
C1 C4 H4 111.7 . . ?
C1 C4 C5 113.23(13) . . ?
C1 C4 C3 104.75(12) . . ?
C5 C4 H4 111.7 . . ?
C3 C4 H4 111.7 . . ?
C3 C4 C5 103.21(12) . . ?
C4 C5 H5 116.3 . . ?
C9 C5 C4 100.33(12) . . ?
C9 C5 H5 116.3 . . ?
C6 C5 C4 105.07(13) . . ?
C6 C5 H5 116.3 . . ?
C6 C5 C9 100.13(14) . . ?
H11A C11 H11B 108.4 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C12 C11 C10 107.95(13) . . ?
C16 C15 C10 121.56(14) . . ?
C16 C15 C14 119.29(15) . . ?
C14 C15 C10 119.13(14) . . ?
N1 C10 C11 111.64(12) . . ?
N1 C10 C15 112.07(13) . . ?
N1 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
C15 C10 C11 111.87(13) . . ?
C15 C10 H10 107.0 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.43(16) . . ?
C17 C16 H16 119.3 . . ?
C15 C14 C13 122.37(15) . . ?
C19 C14 C15 118.45(16) . . ?
C19 C14 C13 119.12(15) . . ?
C9 C8 H8 116.4 . . ?
C9 C8 C3 101.05(14) . . ?
C3 C8 H8 116.4 . . ?
C7 C8 H8 116.4 . . ?
C7 C8 C9 99.92(15) . . ?
C7 C8 C3 104.32(15) . . ?
C5 C9 C8 93.51(14) . . ?
C5 C9 H9A 113.0 . . ?
C5 C9 H9B 113.0 . . ?
C8 C9 H9A 113.0 . . ?
C8 C9 H9B 113.0 . . ?
H9A C9 H9B 110.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 C13 110.59(15) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C2 C3 C4 105.23(12) . . ?
C2 C3 C8 113.25(14) . . ?
C2 C3 H3 111.6 . . ?
C4 C3 C8 103.12(13) . . ?
C4 C3 H3 111.6 . . ?
C8 C3 H3 111.6 . . ?
C5 C6 H6 125.9 . . ?
C7 C6 C5 108.27(15) . . ?
C7 C6 H6 125.9 . . ?
C8 C7 H7 126.2 . . ?
C6 C7 C8 107.61(16) . . ?
C6 C7 H7 126.2 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.53(17) . . ?
C18 C17 H17 120.2 . . ?
C14 C19 H19 119.0 . . ?
C18 C19 C14 121.93(16) . . ?
C18 C19 H19 119.0 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.34(16) . . ?
C19 C18 H18 120.3 . . ?
C14 C13 C12 114.76(15) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?

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 C1 C4 C5 -66.0(2) . . . . ?
O1 C1 C4 C3 -177.72(15) . . . . ?
O2 C2 C3 C4 -178.53(15) . . . . ?
O2 C2 C3 C8 69.6(2) . . . . ?
N1 C1 C4 C5 114.10(14) . . . . ?
N1 C1 C4 C3 2.37(16) . . . . ?
N1 C2 C3 C4 1.83(16) . . . . ?
N1 C2 C3 C8 -110.07(15) . . . . ?
C1 N1 C2 O2 179.98(14) . . . . ?
C1 N1 C2 C3 -0.36(17) . . . . ?
C1 N1 C10 C11 117.35(15) . . . . ?
C1 N1 C10 C15 -116.26(15) . . . . ?
C1 C4 C5 C9 -74.33(16) . . . . ?
C1 C4 C5 C6 -177.87(13) . . . . ?
C1 C4 C3 C2 -2.49(15) . . . . ?
C1 C4 C3 C8 116.43(14) . . . . ?
C2 N1 C1 O1 178.77(14) . . . . ?
C2 N1 C1 C4 -1.32(17) . . . . ?
C2 N1 C10 C11 -58.79(18) . . . . ?
C2 N1 C10 C15 67.60(18) . . . . ?
C4 C5 C9 C8 -58.00(15) . . . . ?
C4 C5 C6 C7 71.09(17) . . . . ?
C5 C4 C3 C2 -121.22(13) . . . . ?
C5 C4 C3 C8 -2.31(15) . . . . ?
C5 C6 C7 C8 -1.10(19) . . . . ?
C11 C12 C13 C14 39.5(2) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C15 C14 C13 C12 -9.7(3) . . . . ?
C10 N1 C1 O1 2.2(2) . . . . ?
C10 N1 C1 C4 -177.87(13) . . . . ?
C10 N1 C2 O2 -3.5(2) . . . . ?
C10 N1 C2 C3 176.13(13) . . . . ?
C10 C11 C12 C13 -63.68(18) . . . . ?
C10 C15 C16 C17 178.66(16) . . . . ?
C10 C15 C14 C19 -178.33(15) . . . . ?
C10 C15 C14 C13 4.4(2) . . . . ?
C16 C15 C10 N1 26.3(2) . . . . ?
C16 C15 C10 C11 152.61(15) . . . . ?
C16 C15 C14 C19 0.1(2) . . . . ?
C16 C15 C14 C13 -177.18(16) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C14 C15 C10 N1 -155.29(14) . . . . ?
C14 C15 C10 C11 -29.0(2) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C14 C19 C18 C17 -0.6(3) . . . . ?
C9 C5 C6 C7 -32.60(17) . . . . ?
C9 C8 C3 C2 78.87(17) . . . . ?
C9 C8 C3 C4 -34.31(16) . . . . ?
C9 C8 C7 C6 34.20(18) . . . . ?
C12 C11 C10 N1 -175.39(13) . . . . ?
C12 C11 C10 C15 58.11(16) . . . . ?
C3 C4 C5 C9 38.34(15) . . . . ?
C3 C4 C5 C6 -65.20(15) . . . . ?
C3 C8 C9 C5 56.66(15) . . . . ?
C3 C8 C7 C6 -70.01(18) . . . . ?
C6 C5 C9 C8 49.52(14) . . . . ?
C7 C8 C9 C5 -50.20(15) . . . . ?
C7 C8 C3 C2 -177.77(14) . . . . ?
C7 C8 C3 C4 69.05(16) . . . . ?
C19 C14 C13 C12 173.08(17) . . . . ?
C13 C14 C19 C18 177.43(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
