# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_D59ZB65_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217472'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 N O2'
_chemical_formula_sum            'C19 H24 N O2'
_chemical_formula_weight         298.39

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.3675(16)
_cell_length_b                   6.3104(4)
_cell_length_c                   11.8556(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.927(2)
_cell_angle_gamma                90
_cell_volume                     1597.97(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7418
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      26.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10863
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3131
_reflns_number_gt                2950
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.919
_reflns_Friedel_fraction_full    0.935

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0418P)²+4.1827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.74978(12) 0.7842(5) 0.8310(2) 0.0331(7) Uani 1 1 d . . . . .
O2 O 0.63605(15) 0.2084(6) 0.7154(4) 0.0662(12) Uani 1 1 d . . . . .
N1 N 0.67138(13) 0.5483(5) 0.7516(3) 0.0257(7) Uani 1 1 d . . . . .
C1 C 0.70547(16) 0.6912(7) 0.8382(3) 0.0265(8) Uani 1 1 d . . . . .
C2 C 0.68901(18) 0.7283(8) 0.9476(3) 0.0360(9) Uani 1 1 d . . . . .
H2A H 0.677274 0.879152 0.947307 0.043 Uiso 1 1 calc R U . . .
H2AB H 0.727084 0.703945 1.023877 0.043 Uiso 1 1 calc R U . . .
C3 C 0.63570(19) 0.5910(9) 0.9541(4) 0.0451(13) Uani 1 1 d . . . . .
H3A H 0.643442 0.567273 1.041639 0.054 Uiso 1 1 calc R U . . .
H3AB H 0.595550 0.668141 0.914447 0.054 Uiso 1 1 calc R U . . .
C4 C 0.63048(19) 0.3784(8) 0.8907(4) 0.0424(11) Uani 1 1 d . . . . .
H4 H 0.671677 0.305949 0.934498 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5798(2) 0.2217(10) 0.8933(5) 0.0573(15) Uani 1 1 d . . . . .
H5 H 0.586518 0.085669 0.857175 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5137(2) 0.2998(11) 0.8082(4) 0.0542(14) Uani 1 1 d . . . . .
H6A H 0.482127 0.197775 0.811046 0.065 Uiso 1 1 calc R U . . .
H6AB H 0.505679 0.438276 0.838303 0.065 Uiso 1 1 calc R U . . .
C7 C 0.50724(18) 0.3225(9) 0.6784(4) 0.0411(11) Uani 1 1 d . . . . .
H7A H 0.464682 0.374808 0.626554 0.049 Uiso 1 1 calc R U . . .
H7AB H 0.512304 0.181829 0.646644 0.049 Uiso 1 1 calc R U . . .
C8 C 0.55608(17) 0.4768(7) 0.6682(3) 0.0302(9) Uani 1 1 d . . . . .
H8 H 0.554624 0.458355 0.583254 0.036 Uiso 1 1 calc R U . . .
C9 C 0.62264(18) 0.4071(7) 0.7592(4) 0.0329(9) Uani 1 1 d . . . . .
C10 C 0.5871(2) 0.1730(11) 1.0196(5) 0.071(2) Uani 1 1 d . . . . .
H10A H 0.559354 0.055512 1.017765 0.106 Uiso 1 1 calc R U . . .
H10B H 0.576294 0.298244 1.055744 0.106 Uiso 1 1 calc R U . . .
H10C H 0.630647 0.132863 1.069475 0.106 Uiso 1 1 calc R U . . .
C11 C 0.53882(18) 0.7080(8) 0.6776(3) 0.0331(9) Uani 1 1 d . . . . .
H11A H 0.575200 0.798599 0.692070 0.050 Uiso 1 1 calc R U . . .
H11B H 0.525952 0.723348 0.746213 0.050 Uiso 1 1 calc R U . . .
H11C H 0.504243 0.750284 0.600462 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6793(5) 0.2270(10) 0.6692(7) 0.097(3) Uani 1 1 d . . . . .
H12 H 0.695848 0.112687 0.639565 0.116 Uiso 1 1 calc R U . . .
C13 C 0.6978(2) 0.4523(7) 0.6708(4) 0.0329(9) Uani 1 1 d . . . . .
H13 H 0.744452 0.461407 0.712851 0.040 Uiso 1 1 calc R U . . .
C14 C 0.67707(16) 0.5498(7) 0.5425(3) 0.0261(8) Uani 1 1 d . . . . .
C15 C 0.64372(17) 0.7378(7) 0.5101(3) 0.0288(8) Uani 1 1 d . . . . .
H15 H 0.631890 0.808965 0.567909 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6274(2) 0.8227(8) 0.3921(4) 0.0384(10) Uani 1 1 d . . . . .
H16 H 0.605598 0.953617 0.370589 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6432(2) 0.7162(10) 0.3071(4) 0.0470(12) Uani 1 1 d . . . . .
H17 H 0.631109 0.772385 0.226401 0.056 Uiso 1 1 calc R U . . .
C18 C 0.67612(19) 0.5293(9) 0.3383(4) 0.0417(11) Uani 1 1 d . . . . .
H18 H 0.686899 0.457109 0.279376 0.050 Uiso 1 1 calc R U . . .
C19 C 0.69355(18) 0.4465(7) 0.4555(4) 0.0348(9) Uani 1 1 d . . . . .
H19 H 0.716908 0.318535 0.477191 0.042 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 1.223(5) . ?
O2 C12 1.337(7) . ?
O2 C9 1.439(5) . ?
N1 C1 1.356(5) . ?
N1 C13 1.464(5) . ?
N1 C9 1.478(5) . ?
C1 C2 1.513(5) . ?
C2 C3 1.545(6) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.518(8) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.505(6) . ?
C4 C5 1.553(6) . ?
C4 H4 1.0000 . ?
C5 C10 1.468(7) . ?
C5 C6 1.543(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.491(6) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.542(6) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C11 1.530(6) . ?
C8 C9 1.554(5) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.483(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.526(5) . ?
C13 H13 1.0000 . ?
C14 C15 1.385(5) . ?
C14 C19 1.400(5) . ?
C15 C16 1.398(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(6) . ?
C18 H18 0.9500 . ?
C19 H19 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
C12 O2 C9 112.5(4) . . ?
C1 N1 C13 119.8(3) . . ?
C1 N1 C9 125.8(3) . . ?
C13 N1 C9 109.3(3) . . ?
O1 C1 N1 121.3(3) . . ?
O1 C1 C2 120.2(4) . . ?
N1 C1 C2 118.5(3) . . ?
C1 C2 C3 116.5(4) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2AB 108.2 . . ?
C3 C2 H2AB 108.2 . . ?
H2A C2 H2AB 107.3 . . ?
C4 C3 C2 112.1(4) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3AB 109.2 . . ?
C2 C3 H3AB 109.2 . . ?
H3A C3 H3AB 107.9 . . ?
C9 C4 C3 111.0(4) . . ?
C9 C4 C5 108.9(4) . . ?
C3 C4 C5 117.5(4) . . ?
C9 C4 H4 106.3 . . ?
C3 C4 H4 106.3 . . ?
C5 C4 H4 106.3 . . ?
C10 C5 C6 113.9(4) . . ?
C10 C5 C4 112.3(4) . . ?
C6 C5 C4 110.6(4) . . ?
C10 C5 H5 106.5 . . ?
C6 C5 H5 106.5 . . ?
C4 C5 H5 106.5 . . ?
C7 C6 C5 111.2(4) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6AB 109.4 . . ?
C5 C6 H6AB 109.4 . . ?
H6A C6 H6AB 108.0 . . ?
C6 C7 C8 111.9(4) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7AB 109.2 . . ?
C8 C7 H7AB 109.2 . . ?
H7A C7 H7AB 107.9 . . ?
C11 C8 C7 111.8(3) . . ?
C11 C8 C9 116.0(3) . . ?
C7 C8 C9 109.3(3) . . ?
C11 C8 H8 106.4 . . ?
C7 C8 H8 106.4 . . ?
C9 C8 H8 106.4 . . ?
O2 C9 N1 102.5(3) . . ?
O2 C9 C4 108.4(4) . . ?
N1 C9 C4 111.3(3) . . ?
O2 C9 C8 107.4(3) . . ?
N1 C9 C8 111.5(3) . . ?
C4 C9 C8 114.9(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 110.1(5) . . ?
O2 C12 H12 125.0 . . ?
C13 C12 H12 125.0 . . ?
N1 C13 C12 102.0(4) . . ?
N1 C13 C14 115.9(3) . . ?
C12 C13 C14 113.6(4) . . ?
N1 C13 H13 108.3 . . ?
C12 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C15 C14 C19 119.1(4) . . ?
C15 C14 C13 122.5(3) . . ?
C19 C14 C13 118.4(4) . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?

_refine_diff_density_max         0.689
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_D59ZB41_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217474'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   10.1771(3)
_cell_length_b                   6.3005(2)
_cell_length_c                   13.2560(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.8700(10)
_cell_angle_gamma                90
_cell_volume                     788.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8840
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      71.89

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.635
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5838
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13380
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.593
_diffrn_reflns_theta_max         71.948
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3061
_reflns_number_gt                2922
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.985

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3061
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.44865(15) 0.5241(3) -0.01091(10) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.47379(13) 0.2503(2) 0.30664(10) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.47545(16) 0.4527(2) 0.16384(12) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.5264(2) 0.4997(3) 0.08459(15) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.6844(2) 0.5300(4) 0.12476(16) 0.0268(4) Uani 1 1 d . . . . .
H2A H 0.707879 0.671855 0.158914 0.032 Uiso 1 1 calc R U . . .
H2AB H 0.713969 0.527715 0.061576 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7703(2) 0.3615(4) 0.20739(16) 0.0280(4) Uani 1 1 d . . . . .
H3A H 0.810850 0.260022 0.169824 0.034 Uiso 1 1 calc R U . . .
H3AB H 0.850194 0.432719 0.264756 0.034 Uiso 1 1 calc R U . . .
C4 C 0.68506(19) 0.2371(3) 0.26135(15) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.638751 0.115207 0.212817 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7802(2) 0.1462(3) 0.37186(15) 0.0224(4) Uani 1 1 d . . . . .
H5A H 0.725344 0.042456 0.396434 0.027 Uiso 1 1 calc R U . . .
H5AB H 0.860569 0.069932 0.363510 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8375(2) 0.3187(3) 0.45818(15) 0.0231(4) Uani 1 1 d . . . . .
H6A H 0.903470 0.410566 0.438812 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.891409 0.251400 0.529087 0.028 Uiso 1 1 calc R U . . .
C7 C 0.71941(19) 0.4553(3) 0.46910(15) 0.0207(4) Uani 1 1 d . . . . .
H7 H 0.658135 0.360936 0.493684 0.025 Uiso 1 1 calc R U . . .
C8 C 0.62548(18) 0.5527(3) 0.35863(14) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.687006 0.646438 0.333967 0.022 Uiso 1 1 calc R U . . .
C9 C 0.56807(18) 0.3753(3) 0.27360(14) 0.0178(4) Uani 1 1 d . . . . .
C10 C 0.36154(19) 0.1784(3) 0.21075(15) 0.0231(4) Uani 1 1 d . . . . .
H10A H 0.276931 0.140567 0.226805 0.028 Uiso 1 1 calc R U . . .
H10B H 0.391366 0.053035 0.179590 0.028 Uiso 1 1 calc R U . . .
C11 C 0.33074(19) 0.3663(3) 0.13310(15) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.298824 0.311387 0.056937 0.026 Uiso 1 1 calc R U . . .
C12 C 0.22544(18) 0.5318(3) 0.13927(14) 0.0202(4) Uani 1 1 d . . . . .
C13 C 0.19413(19) 0.6984(3) 0.06444(15) 0.0222(4) Uani 1 1 d . . . . .
H13 H 0.240497 0.705304 0.014186 0.027 Uiso 1 1 calc R U . . .
C14 C 0.09666(19) 0.8539(3) 0.06215(15) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.075171 0.964232 0.009627 0.028 Uiso 1 1 calc R U . . .
C15 C 0.03064(19) 0.8482(3) 0.13654(16) 0.0253(4) Uani 1 1 d . . . . .
H15 H -0.035927 0.954631 0.135550 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0627(2) 0.6850(4) 0.21278(16) 0.0268(4) Uani 1 1 d . . . . .
H16 H 0.018624 0.681203 0.264589 0.032 Uiso 1 1 calc R U . . .
C17 C 0.15886(19) 0.5274(4) 0.21350(15) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.179111 0.415824 0.265283 0.030 Uiso 1 1 calc R U . . .
C18 C 0.50652(19) 0.6898(3) 0.36754(15) 0.0222(4) Uani 1 1 d . . . . .
H18A H 0.442401 0.732044 0.294662 0.033 Uiso 1 1 calc R U . . .
H18B H 0.546999 0.816779 0.410591 0.033 Uiso 1 1 calc R U . . .
H18C H 0.453823 0.608490 0.403094 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7816(2) 0.6254(4) 0.55614(16) 0.0284(5) Uani 1 1 d . . . . .
H19A H 0.834958 0.728258 0.531018 0.043 Uiso 1 1 calc R U . . .
H19B H 0.845005 0.558588 0.623445 0.043 Uiso 1 1 calc R U . . .
H19C H 0.704794 0.698314 0.569762 0.043 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 1.227(2) . ?
O2 C10 1.430(2) . ?
O2 C9 1.430(2) . ?
N1 C1 1.366(2) . ?
N1 C11 1.478(2) . ?
N1 C9 1.491(2) . ?
C1 C2 1.506(3) . ?
C2 C3 1.542(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.532(2) . ?
C4 C5 1.534(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.528(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.528(3) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C19 1.528(3) . ?
C7 C8 1.547(2) . ?
C7 H7 1.0000 . ?
C8 C18 1.527(2) . ?
C8 C9 1.540(2) . ?
C8 H8 1.0000 . ?
C10 C11 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(3) . ?
C11 H11 1.0000 . ?
C12 C17 1.387(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C10 O2 C9 107.89(13) . . ?
C1 N1 C11 119.51(15) . . ?
C1 N1 C9 122.58(15) . . ?
C11 N1 C9 110.58(14) . . ?
O1 C1 N1 122.47(18) . . ?
O1 C1 C2 122.83(17) . . ?
N1 C1 C2 114.63(16) . . ?
C1 C2 C3 114.34(18) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2AB 108.7 . . ?
C3 C2 H2AB 108.7 . . ?
H2A C2 H2AB 107.6 . . ?
C4 C3 C2 114.49(16) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3AB 108.6 . . ?
C2 C3 H3AB 108.6 . . ?
H3A C3 H3AB 107.6 . . ?
C3 C4 C9 110.92(16) . . ?
C3 C4 C5 111.82(16) . . ?
C9 C4 C5 110.47(14) . . ?
C3 C4 H4 107.8 . . ?
C9 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
C6 C5 C4 112.25(16) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5AB 109.2 . . ?
C4 C5 H5AB 109.2 . . ?
H5A C5 H5AB 107.9 . . ?
C5 C6 C7 112.16(15) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6AB 109.2 . . ?
C7 C6 H6AB 109.2 . . ?
H6A C6 H6AB 107.9 . . ?
C6 C7 C19 110.31(15) . . ?
C6 C7 C8 111.37(15) . . ?
C19 C7 C8 111.87(16) . . ?
C6 C7 H7 107.7 . . ?
C19 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
C18 C8 C9 111.81(14) . . ?
C18 C8 C7 112.30(14) . . ?
C9 C8 C7 109.69(15) . . ?
C18 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C7 C8 H8 107.6 . . ?
O2 C9 N1 103.10(13) . . ?
O2 C9 C4 110.87(15) . . ?
N1 C9 C4 108.44(14) . . ?
O2 C9 C8 106.89(13) . . ?
N1 C9 C8 113.99(15) . . ?
C4 C9 C8 113.10(14) . . ?
O2 C10 C11 104.46(15) . . ?
O2 C10 H10A 110.9 . . ?
C11 C10 H10A 110.9 . . ?
O2 C10 H10B 110.9 . . ?
C11 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
N1 C11 C12 112.50(16) . . ?
N1 C11 C10 99.61(14) . . ?
C12 C11 C10 117.97(16) . . ?
N1 C11 H11 108.7 . . ?
C12 C11 H11 108.7 . . ?
C10 C11 H11 108.7 . . ?
C17 C12 C13 118.44(18) . . ?
C17 C12 C11 124.40(18) . . ?
C13 C12 C11 117.16(16) . . ?
C14 C13 C12 121.23(17) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.93(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.43(19) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.36(18) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C12 C17 C16 120.59(19) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_D59ZB1A_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217476'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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                   5.8915(3)
_cell_length_b                   10.8740(7)
_cell_length_c                   25.1352(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1610.27(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6449
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.32

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34286
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4900
_reflns_number_gt                3793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.993
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0306P)²+0.5409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4900
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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 0.7481(3) 0.65706(16) 0.56735(7) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.1504(3) 0.74782(15) 0.66997(7) 0.0223(4) Uani 1 1 d . . . . .
N1 N 0.4731(3) 0.72458(17) 0.62214(8) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.6051(4) 0.7356(2) 0.57858(9) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.5596(4) 0.8417(2) 0.54118(9) 0.0193(5) Uani 1 1 d . . . . .
H2A H 0.507126 0.807251 0.506861 0.023 Uiso 1 1 calc R U . . .
H2AB H 0.705524 0.884002 0.534367 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3876(4) 0.9381(2) 0.55902(10) 0.0212(5) Uani 1 1 d . . . . .
H3A H 0.312798 0.973481 0.527250 0.025 Uiso 1 1 calc R U . . .
H3AB H 0.468591 1.005406 0.577517 0.025 Uiso 1 1 calc R U . . .
C4 C 0.2058(4) 0.8856(2) 0.59621(9) 0.0185(5) Uani 1 1 d . . . . .
H4 H 0.115264 0.824103 0.575610 0.022 Uiso 1 1 calc R U . . .
C5 C 0.0427(4) 0.9851(2) 0.61597(10) 0.0221(5) Uani 1 1 d . . . . .
H5A H -0.088595 0.944971 0.633363 0.026 Uiso 1 1 calc R U . . .
H5AB H -0.015132 1.031689 0.584972 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1509(4) 1.0753(2) 0.65523(10) 0.0218(5) Uani 1 1 d . . . . .
H6 H 0.274215 1.120438 0.636130 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2591(4) 1.0036(2) 0.70077(10) 0.0215(5) Uani 1 1 d . . . . .
H7A H 0.139024 0.959904 0.720847 0.026 Uiso 1 1 calc R U . . .
H7AB H 0.334203 1.061804 0.725393 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4344(4) 0.9098(2) 0.68068(9) 0.0199(5) Uani 1 1 d . . . . .
H8 H 0.547681 0.956675 0.659101 0.024 Uiso 1 1 calc R U . . .
C9 C 0.3177(4) 0.8185(2) 0.64254(10) 0.0183(5) Uani 1 1 d . . . . .
C10 C 0.2525(5) 0.6357(2) 0.68795(11) 0.0277(6) Uani 1 1 d . . . . .
H10A H 0.140482 0.567886 0.686829 0.033 Uiso 1 1 calc R U . . .
H10B H 0.306463 0.644998 0.725036 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4527(4) 0.6073(2) 0.65089(10) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.593059 0.591413 0.672185 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4056(4) 0.5000(2) 0.61406(9) 0.0188(5) Uani 1 1 d . . . . .
C13 C 0.2062(4) 0.4953(2) 0.58509(10) 0.0250(5) Uani 1 1 d . . . . .
H13 H 0.099754 0.560685 0.587554 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1613(5) 0.3952(2) 0.55237(11) 0.0290(6) Uani 1 1 d . . . . .
H14 H 0.024082 0.392415 0.532538 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3154(5) 0.2994(2) 0.54852(11) 0.0280(6) Uani 1 1 d . . . . .
H15 H 0.283954 0.230959 0.526201 0.034 Uiso 1 1 calc R U . . .
C16 C 0.5147(4) 0.3038(2) 0.57726(11) 0.0261(5) Uani 1 1 d . . . . .
H16 H 0.621320 0.238557 0.574607 0.031 Uiso 1 1 calc R U . . .
C17 C 0.5598(4) 0.4039(2) 0.61015(10) 0.0229(5) Uani 1 1 d . . . . .
H17 H 0.696841 0.406463 0.630021 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0215(5) 1.1693(2) 0.67448(11) 0.0299(6) Uani 1 1 d . . . . .
H18A H -0.070932 1.220209 0.644462 0.045 Uiso 1 1 calc R U . . .
H18B H 0.048076 1.221661 0.701692 0.045 Uiso 1 1 calc R U . . .
H18C H -0.152910 1.126627 0.689689 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5645(5) 0.8514(2) 0.72681(11) 0.0293(6) Uani 1 1 d . . . . .
H19A H 0.667140 0.788088 0.713033 0.044 Uiso 1 1 calc R U . . .
H19B H 0.456857 0.813992 0.751747 0.044 Uiso 1 1 calc R U . . .
H19C H 0.652821 0.914793 0.745248 0.044 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 1.233(3) . ?
O2 C9 1.427(3) . ?
O2 C10 1.433(3) . ?
N1 C1 1.348(3) . ?
N1 C9 1.465(3) . ?
N1 C11 1.471(3) . ?
C1 C2 1.512(3) . ?
C2 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.532(3) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.524(3) . ?
C4 C5 1.529(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.530(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C18 1.520(3) . ?
C6 C7 1.525(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.537(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C19 1.528(4) . ?
C8 C9 1.542(3) . ?
C8 H8 1.0000 . ?
C10 C11 1.535(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.383(3) . ?
C12 C17 1.388(3) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C9 O2 C10 108.72(18) . . ?
C1 N1 C9 125.66(19) . . ?
C1 N1 C11 121.53(19) . . ?
C9 N1 C11 112.45(18) . . ?
O1 C1 N1 121.2(2) . . ?
O1 C1 C2 120.5(2) . . ?
N1 C1 C2 118.06(19) . . ?
C1 C2 C3 117.34(19) . . ?
C1 C2 H2A 108.0 . . ?
C3 C2 H2A 108.0 . . ?
C1 C2 H2AB 108.0 . . ?
C3 C2 H2AB 108.0 . . ?
H2A C2 H2AB 107.2 . . ?
C2 C3 C4 112.84(19) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3AB 109.0 . . ?
C4 C3 H3AB 109.0 . . ?
H3A C3 H3AB 107.8 . . ?
C9 C4 C5 111.22(19) . . ?
C9 C4 C3 110.01(19) . . ?
C5 C4 C3 111.96(19) . . ?
C9 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
C4 C5 C6 113.6(2) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5AB 108.8 . . ?
C6 C5 H5AB 108.8 . . ?
H5A C5 H5AB 107.7 . . ?
C18 C6 C7 112.6(2) . . ?
C18 C6 C5 111.0(2) . . ?
C7 C6 C5 109.3(2) . . ?
C18 C6 H6 107.9 . . ?
C7 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C6 C7 C8 111.94(19) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7AB 109.2 . . ?
C8 C7 H7AB 109.2 . . ?
H7A C7 H7AB 107.9 . . ?
C19 C8 C7 111.3(2) . . ?
C19 C8 C9 115.4(2) . . ?
C7 C8 C9 109.4(2) . . ?
C19 C8 H8 106.8 . . ?
C7 C8 H8 106.8 . . ?
C9 C8 H8 106.8 . . ?
O2 C9 N1 103.00(17) . . ?
O2 C9 C4 109.17(18) . . ?
N1 C9 C4 109.68(19) . . ?
O2 C9 C8 110.74(19) . . ?
N1 C9 C8 112.82(19) . . ?
C4 C9 C8 111.10(18) . . ?
O2 C10 C11 107.60(19) . . ?
O2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N1 C11 C12 112.50(19) . . ?
N1 C11 C10 100.75(18) . . ?
C12 C11 C10 112.6(2) . . ?
N1 C11 H11 110.2 . . ?
C12 C11 H11 110.2 . . ?
C10 C11 H11 110.2 . . ?
C13 C12 C17 119.4(2) . . ?
C13 C12 C11 120.4(2) . . ?
C17 C12 C11 120.2(2) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.4(2) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_D59ZB7_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217475'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C19 H25 N O2), H2 O'
_chemical_formula_sum            'C76 H102 N4 O9'
_chemical_formula_weight         1215.61

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   28.4604(11)
_cell_length_b                   8.5623(3)
_cell_length_c                   13.3639(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.7390(10)
_cell_angle_gamma                90
_cell_volume                     3252.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      30.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             1316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27198
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         30.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             9714
_reflns_number_gt                8768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.986

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0430P)²+1.2456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         9714
_refine_ls_number_parameters     409
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.026
_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
O1A O 0.54649(5) 0.09605(15) 0.64554(10) 0.0246(3) Uani 1 1 d D . . . .
O2A O 0.43650(5) 0.17766(16) 0.87098(9) 0.0232(3) Uani 1 1 d . . . . .
N1A N 0.48600(5) 0.11838(17) 0.74846(11) 0.0177(3) Uani 1 1 d . . . . .
C1A C 0.52015(6) 0.0363(2) 0.70517(12) 0.0198(3) Uani 1 1 d . . . . .
C2A C 0.52780(8) -0.1310(2) 0.73887(16) 0.0273(4) Uani 1 1 d . . . . .
H2AA H 0.559393 -0.137566 0.772992 0.033 Uiso 1 1 calc R U . . .
H2AB H 0.528392 -0.197129 0.678172 0.033 Uiso 1 1 calc R U . . .
C3A C 0.49258(7) -0.2028(2) 0.80835(14) 0.0226(3) Uani 1 1 d . . . . .
H3AA H 0.508792 -0.281960 0.851561 0.027 Uiso 1 1 calc R U . . .
H3AB H 0.467502 -0.256455 0.767566 0.027 Uiso 1 1 calc R U . . .
C4A C 0.47025(6) -0.0797(2) 0.87453(13) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.495740 -0.032888 0.919078 0.025 Uiso 1 1 calc R U . . .
C5A C 0.43301(7) -0.1473(3) 0.94092(14) 0.0278(4) Uani 1 1 d . . . . .
H5AA H 0.446469 -0.238005 0.978245 0.033 Uiso 1 1 calc R U . . .
H5AB H 0.424387 -0.067568 0.990443 0.033 Uiso 1 1 calc R U . . .
C6A C 0.38875(7) -0.1991(3) 0.88078(15) 0.0289(4) Uani 1 1 d . . . . .
H6AA H 0.364567 -0.230267 0.927737 0.035 Uiso 1 1 calc R U . . .
H6AB H 0.396281 -0.291757 0.840274 0.035 Uiso 1 1 calc R U . . .
C7A C 0.36851(7) -0.0713(2) 0.81113(14) 0.0250(4) Uani 1 1 d . . . . .
H7A H 0.358213 0.017106 0.853802 0.030 Uiso 1 1 calc R U . . .
C8A C 0.40637(6) -0.0084(2) 0.74256(13) 0.0202(3) Uani 1 1 d . . . . .
H8A H 0.417550 -0.099355 0.703196 0.024 Uiso 1 1 calc R U . . .
C9A C 0.44903(6) 0.0502(2) 0.80808(12) 0.0180(3) Uani 1 1 d . . . . .
C10A C 0.44459(7) 0.3218(2) 0.81994(15) 0.0242(4) Uani 1 1 d . . . . .
H10A H 0.454178 0.404394 0.868604 0.029 Uiso 1 1 calc R U . . .
H10B H 0.415595 0.356117 0.782336 0.029 Uiso 1 1 calc R U . . .
C11A C 0.48431(6) 0.2909(2) 0.74720(13) 0.0190(3) Uani 1 1 d . . . . .
H11A H 0.474708 0.329133 0.678518 0.023 Uiso 1 1 calc R U . . .
C12A C 0.53042(7) 0.3651(2) 0.78260(13) 0.0202(3) Uani 1 1 d . . . . .
C13A C 0.55363(7) 0.4649(2) 0.71905(14) 0.0224(4) Uani 1 1 d . . . . .
H13A H 0.541889 0.478808 0.651894 0.027 Uiso 1 1 calc R U . . .
C14A C 0.59398(7) 0.5444(2) 0.75345(15) 0.0256(4) Uani 1 1 d . . . . .
H14A H 0.609495 0.612892 0.709865 0.031 Uiso 1 1 calc R U . . .
C15A C 0.61155(7) 0.5238(2) 0.85119(15) 0.0267(4) Uani 1 1 d . . . . .
H15A H 0.638686 0.579617 0.874934 0.032 Uiso 1 1 calc R U . . .
C16A C 0.58937(7) 0.4212(3) 0.91428(15) 0.0282(4) Uani 1 1 d . . . . .
H16A H 0.601823 0.405002 0.980690 0.034 Uiso 1 1 calc R U . . .
C17A C 0.54891(7) 0.3422(2) 0.88034(14) 0.0247(4) Uani 1 1 d . . . . .
H17A H 0.533799 0.272468 0.923767 0.030 Uiso 1 1 calc R U . . .
C18A C 0.32506(8) -0.1331(3) 0.75165(18) 0.0346(5) Uani 1 1 d . . . . .
H18A H 0.301696 -0.168630 0.798160 0.052 Uiso 1 1 calc R U . . .
H18B H 0.334167 -0.220659 0.709497 0.052 Uiso 1 1 calc R U . . .
H18C H 0.311517 -0.049580 0.709239 0.052 Uiso 1 1 calc R U . . .
C19A C 0.38687(7) 0.1118(2) 0.66671(14) 0.0255(4) Uani 1 1 d . . . . .
H19A H 0.370798 0.195002 0.701992 0.038 Uiso 1 1 calc R U . . .
H19B H 0.364549 0.060721 0.619127 0.038 Uiso 1 1 calc R U . . .
H19C H 0.412792 0.156524 0.630422 0.038 Uiso 1 1 calc R U . . .
O1B O 0.71050(5) 1.0468(2) 0.48537(10) 0.0309(3) Uani 1 1 d . . . . .
O2B O 0.69416(5) 0.76277(16) 0.76430(10) 0.0254(3) Uani 1 1 d . . . . .
N1B N 0.70918(5) 0.92231(18) 0.63408(11) 0.0194(3) Uani 1 1 d . . . . .
C1B C 0.70603(6) 1.0522(2) 0.57613(14) 0.0230(4) Uani 1 1 d . . . . .
C2B C 0.69652(9) 1.2025(2) 0.63055(17) 0.0337(5) Uani 1 1 d . . . . .
H2BA H 0.679669 1.274110 0.583043 0.040 Uiso 1 1 calc R U . . .
H2BB H 0.727129 1.251533 0.649871 0.040 Uiso 1 1 calc R U . . .
C3B C 0.66780(8) 1.1892(3) 0.72516(18) 0.0336(5) Uani 1 1 d . . . . .
H3BA H 0.683054 1.255020 0.778275 0.040 Uiso 1 1 calc R U . . .
H3BB H 0.636078 1.232966 0.709653 0.040 Uiso 1 1 calc R U . . .
C4B C 0.66209(6) 1.0230(2) 0.76717(14) 0.0239(4) Uani 1 1 d . . . . .
H4B H 0.633740 0.975567 0.732026 0.029 Uiso 1 1 calc R U . . .
C5B C 0.65396(7) 1.0212(3) 0.87953(16) 0.0330(4) Uani 1 1 d . . . . .
H5BA H 0.628513 1.095594 0.893761 0.040 Uiso 1 1 calc R U . . .
H5BB H 0.643572 0.915565 0.899002 0.040 Uiso 1 1 calc R U . . .
C6B C 0.69811(8) 1.0648(3) 0.94229(16) 0.0364(5) Uani 1 1 d . . . . .
H6BA H 0.692014 1.051454 1.014105 0.044 Uiso 1 1 calc R U . . .
H6BB H 0.705446 1.176272 0.931051 0.044 Uiso 1 1 calc R U . . .
C7B C 0.74060(8) 0.9657(3) 0.91703(15) 0.0299(4) Uani 1 1 d . . . . .
H7B H 0.733229 0.854376 0.932729 0.036 Uiso 1 1 calc R U . . .
C8B C 0.74933(6) 0.9764(2) 0.80337(14) 0.0235(4) Uani 1 1 d . . . . .
H8B H 0.754134 1.089259 0.787406 0.028 Uiso 1 1 calc R U . . .
C9B C 0.70437(6) 0.9225(2) 0.74347(13) 0.0187(3) Uani 1 1 d . . . . .
C10B C 0.71298(8) 0.6674(2) 0.68774(16) 0.0290(4) Uani 1 1 d . . . . .
H10C H 0.695456 0.567781 0.680728 0.035 Uiso 1 1 calc R U . . .
H10D H 0.746593 0.643992 0.703401 0.035 Uiso 1 1 calc R U . . .
C11B C 0.70697(7) 0.7651(2) 0.59165(14) 0.0238(4) Uani 1 1 d . . . . .
H11B H 0.734017 0.747249 0.547937 0.029 Uiso 1 1 calc R U . . .
C12B C 0.66062(7) 0.7270(2) 0.53475(13) 0.0237(4) Uani 1 1 d . . . . .
C13B C 0.65820(9) 0.5834(2) 0.48471(16) 0.0346(5) Uani 1 1 d . . . . .
H13B H 0.685657 0.521019 0.481004 0.042 Uiso 1 1 calc R U . . .
C14B C 0.61590(10) 0.5317(3) 0.44049(18) 0.0440(6) Uani 1 1 d . . . . .
H14B H 0.614350 0.432923 0.408073 0.053 Uiso 1 1 calc R U . . .
C15B C 0.57594(10) 0.6236(3) 0.44349(17) 0.0405(6) Uani 1 1 d . . . . .
H15B H 0.546933 0.587282 0.414026 0.049 Uiso 1 1 calc R U . . .
C16B C 0.57830(8) 0.7687(3) 0.48951(15) 0.0310(4) Uani 1 1 d . . . . .
H16B H 0.551152 0.833235 0.489874 0.037 Uiso 1 1 calc R U . . .
C17B C 0.62059(7) 0.8197(2) 0.53523(13) 0.0246(4) Uani 1 1 d . . . . .
H17B H 0.622054 0.918960 0.567042 0.029 Uiso 1 1 calc R U . . .
C18B C 0.78360(9) 1.0137(3) 0.98249(18) 0.0412(6) Uani 1 1 d . . . . .
H18D H 0.775716 1.011995 1.053062 0.062 Uiso 1 1 calc R U . . .
H18E H 0.793287 1.119339 0.964225 0.062 Uiso 1 1 calc R U . . .
H18F H 0.809414 0.940541 0.972197 0.062 Uiso 1 1 calc R U . . .
C19B C 0.79391(7) 0.8894(3) 0.77606(17) 0.0342(5) Uani 1 1 d . . . . .
H19D H 0.793760 0.784308 0.805072 0.051 Uiso 1 1 calc R U . . .
H19E H 0.821640 0.946472 0.802607 0.051 Uiso 1 1 calc R U . . .
H19F H 0.794889 0.881742 0.703024 0.051 Uiso 1 1 calc R U . . .
O1W O 0.500000 0.2973(3) 0.500000 0.0397(6) Uani 1 2 d DS T P . .
H1WA H 0.5170(9) 0.240(3) 0.5368(19) 0.048 Uiso 1 1 d D 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
O1A C1A 1.231(2) . ?
O2A C9A 1.433(2) . ?
O2A C10A 1.434(2) . ?
N1A C1A 1.352(2) . ?
N1A C9A 1.471(2) . ?
N1A C11A 1.478(2) . ?
C1A C2A 1.515(3) . ?
C2A C3A 1.528(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.534(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C5A 1.528(3) . ?
C4A C9A 1.529(2) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.527(3) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C7A 1.531(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C18A 1.532(3) . ?
C7A C8A 1.544(3) . ?
C7A H7A 1.0000 . ?
C8A C19A 1.530(3) . ?
C8A C9A 1.546(2) . ?
C8A H8A 1.0000 . ?
C10A C11A 1.549(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.513(3) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.393(3) . ?
C12A C17A 1.398(3) . ?
C13A C14A 1.394(3) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.387(3) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.390(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.393(3) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
O1B C1B 1.226(2) . ?
O2B C9B 1.429(2) . ?
O2B C10B 1.433(3) . ?
N1B C1B 1.355(2) . ?
N1B C11B 1.461(2) . ?
N1B C9B 1.475(2) . ?
C1B C2B 1.509(3) . ?
C2B C3B 1.542(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.542(3) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C4B C9B 1.525(2) . ?
C4B C5B 1.530(3) . ?
C4B H4B 1.0000 . ?
C5B C6B 1.523(3) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C7B 1.528(3) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C18B 1.526(3) . ?
C7B C8B 1.553(3) . ?
C7B H7B 1.0000 . ?
C8B C19B 1.531(3) . ?
C8B C9B 1.547(2) . ?
C8B H8B 1.0000 . ?
C10B C11B 1.535(3) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.526(3) . ?
C11B H11B 1.0000 . ?
C12B C17B 1.389(3) . ?
C12B C13B 1.400(3) . ?
C13B C14B 1.388(4) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.385(4) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.386(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.394(3) . ?
C16B H16B 0.9500 . ?
C17B H17B 0.9500 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
O1W H1WA 0.834(12) . ?
O1W H1WA 0.834(12) 2_656 ?

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
C9A O2A C10A 109.05(13) . . ?
C1A N1A C9A 124.98(15) . . ?
C1A N1A C11A 122.56(15) . . ?
C9A N1A C11A 112.29(14) . . ?
O1A C1A N1A 122.27(17) . . ?
O1A C1A C2A 120.14(16) . . ?
N1A C1A C2A 117.42(16) . . ?
C1A C2A C3A 118.18(16) . . ?
C1A C2A H2AA 107.8 . . ?
C3A C2A H2AA 107.8 . . ?
C1A C2A H2AB 107.8 . . ?
C3A C2A H2AB 107.8 . . ?
H2AA C2A H2AB 107.1 . . ?
C2A C3A C4A 112.07(15) . . ?
C2A C3A H3AA 109.2 . . ?
C4A C3A H3AA 109.2 . . ?
C2A C3A H3AB 109.2 . . ?
C4A C3A H3AB 109.2 . . ?
H3AA C3A H3AB 107.9 . . ?
C5A C4A C9A 110.32(15) . . ?
C5A C4A C3A 113.08(16) . . ?
C9A C4A C3A 109.15(13) . . ?
C5A C4A H4A 108.0 . . ?
C9A C4A H4A 108.0 . . ?
C3A C4A H4A 108.0 . . ?
C6A C5A C4A 112.45(15) . . ?
C6A C5A H5AA 109.1 . . ?
C4A C5A H5AA 109.1 . . ?
C6A C5A H5AB 109.1 . . ?
C4A C5A H5AB 109.1 . . ?
H5AA C5A H5AB 107.8 . . ?
C5A C6A C7A 112.94(17) . . ?
C5A C6A H6AA 109.0 . . ?
C7A C6A H6AA 109.0 . . ?
C5A C6A H6AB 109.0 . . ?
C7A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
C6A C7A C18A 109.85(17) . . ?
C6A C7A C8A 110.91(16) . . ?
C18A C7A C8A 112.41(16) . . ?
C6A C7A H7A 107.8 . . ?
C18A C7A H7A 107.8 . . ?
C8A C7A H7A 107.8 . . ?
C19A C8A C7A 112.73(15) . . ?
C19A C8A C9A 114.01(15) . . ?
C7A C8A C9A 109.17(14) . . ?
C19A C8A H8A 106.8 . . ?
C7A C8A H8A 106.8 . . ?
C9A C8A H8A 106.8 . . ?
O2A C9A N1A 102.71(13) . . ?
O2A C9A C4A 108.39(13) . . ?
N1A C9A C4A 109.30(14) . . ?
O2A C9A C8A 111.63(14) . . ?
N1A C9A C8A 112.64(13) . . ?
C4A C9A C8A 111.74(15) . . ?
O2A C10A C11A 106.87(14) . . ?
O2A C10A H10A 110.3 . . ?
C11A C10A H10A 110.3 . . ?
O2A C10A H10B 110.3 . . ?
C11A C10A H10B 110.3 . . ?
H10A C10A H10B 108.6 . . ?
N1A C11A C12A 112.88(14) . . ?
N1A C11A C10A 100.82(14) . . ?
C12A C11A C10A 112.34(14) . . ?
N1A C11A H11A 110.2 . . ?
C12A C11A H11A 110.2 . . ?
C10A C11A H11A 110.2 . . ?
C13A C12A C17A 119.16(17) . . ?
C13A C12A C11A 119.74(16) . . ?
C17A C12A C11A 121.00(16) . . ?
C12A C13A C14A 120.36(17) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C15A C14A C13A 120.15(18) . . ?
C15A C14A H14A 119.9 . . ?
C13A C14A H14A 119.9 . . ?
C14A C15A C16A 119.87(18) . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A H15A 120.1 . . ?
C15A C16A C17A 120.11(18) . . ?
C15A C16A H16A 119.9 . . ?
C17A C16A H16A 119.9 . . ?
C16A C17A C12A 120.30(18) . . ?
C16A C17A H17A 119.9 . . ?
C12A C17A H17A 119.9 . . ?
C7A C18A H18A 109.5 . . ?
C7A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C7A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C8A C19A H19A 109.5 . . ?
C8A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C8A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C9B O2B C10B 108.67(14) . . ?
C1B N1B C11B 122.25(15) . . ?
C1B N1B C9B 123.95(15) . . ?
C11B N1B C9B 112.43(14) . . ?
O1B C1B N1B 121.80(19) . . ?
O1B C1B C2B 122.56(18) . . ?
N1B C1B C2B 115.64(16) . . ?
C1B C2B C3B 116.52(17) . . ?
C1B C2B H2BA 108.2 . . ?
C3B C2B H2BA 108.2 . . ?
C1B C2B H2BB 108.2 . . ?
C3B C2B H2BB 108.2 . . ?
H2BA C2B H2BB 107.3 . . ?
C4B C3B C2B 115.83(17) . . ?
C4B C3B H3BA 108.3 . . ?
C2B C3B H3BA 108.3 . . ?
C4B C3B H3BB 108.3 . . ?
C2B C3B H3BB 108.3 . . ?
H3BA C3B H3BB 107.4 . . ?
C9B C4B C5B 110.85(16) . . ?
C9B C4B C3B 110.31(16) . . ?
C5B C4B C3B 112.97(18) . . ?
C9B C4B H4B 107.5 . . ?
C5B C4B H4B 107.5 . . ?
C3B C4B H4B 107.5 . . ?
C6B C5B C4B 112.24(17) . . ?
C6B C5B H5BA 109.2 . . ?
C4B C5B H5BA 109.2 . . ?
C6B C5B H5BB 109.2 . . ?
C4B C5B H5BB 109.2 . . ?
H5BA C5B H5BB 107.9 . . ?
C5B C6B C7B 112.49(18) . . ?
C5B C6B H6BA 109.1 . . ?
C7B C6B H6BA 109.1 . . ?
C5B C6B H6BB 109.1 . . ?
C7B C6B H6BB 109.1 . . ?
H6BA C6B H6BB 107.8 . . ?
C18B C7B C6B 110.18(19) . . ?
C18B C7B C8B 112.52(18) . . ?
C6B C7B C8B 110.37(17) . . ?
C18B C7B H7B 107.9 . . ?
C6B C7B H7B 107.9 . . ?
C8B C7B H7B 107.9 . . ?
C19B C8B C9B 113.95(16) . . ?
C19B C8B C7B 112.17(17) . . ?
C9B C8B C7B 108.74(15) . . ?
C19B C8B H8B 107.2 . . ?
C9B C8B H8B 107.2 . . ?
C7B C8B H8B 107.2 . . ?
O2B C9B N1B 102.78(14) . . ?
O2B C9B C4B 109.24(14) . . ?
N1B C9B C4B 108.56(14) . . ?
O2B C9B C8B 110.84(14) . . ?
N1B C9B C8B 113.56(14) . . ?
C4B C9B C8B 111.45(15) . . ?
O2B C10B C11B 104.84(15) . . ?
O2B C10B H10C 110.8 . . ?
C11B C10B H10C 110.8 . . ?
O2B C10B H10D 110.8 . . ?
C11B C10B H10D 110.8 . . ?
H10C C10B H10D 108.9 . . ?
N1B C11B C12B 114.22(15) . . ?
N1B C11B C10B 100.17(15) . . ?
C12B C11B C10B 111.06(16) . . ?
N1B C11B H11B 110.3 . . ?
C12B C11B H11B 110.3 . . ?
C10B C11B H11B 110.3 . . ?
C17B C12B C13B 118.85(19) . . ?
C17B C12B C11B 124.43(16) . . ?
C13B C12B C11B 116.58(19) . . ?
C14B C13B C12B 120.4(2) . . ?
C14B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
C15B C14B C13B 120.2(2) . . ?
C15B C14B H14B 119.9 . . ?
C13B C14B H14B 119.9 . . ?
C14B C15B C16B 120.0(2) . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B C17B 119.9(2) . . ?
C15B C16B H16B 120.1 . . ?
C17B C16B H16B 120.1 . . ?
C12B C17B C16B 120.68(19) . . ?
C12B C17B H17B 119.7 . . ?
C16B C17B H17B 119.7 . . ?
C7B C18B H18D 109.5 . . ?
C7B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C7B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C8B C19B H19D 109.5 . . ?
C8B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C8B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
H1WA O1W H1WA 107(4) . 2_656 ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_D59ZB54_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217473'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.4807(5)
_cell_length_b                   10.7621(5)
_cell_length_c                   8.7322(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.909(2)
_cell_angle_gamma                90
_cell_volume                     789.41(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7017
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12791
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         30.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4701
_reflns_number_gt                4381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.993

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0455P)²+0.1280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4701
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.01462(16) 0.60858(14) 0.34208(16) 0.0204(3) Uani 1 1 d . . . . .
O2 O 0.38013(16) 0.32551(12) 0.49453(16) 0.0173(3) Uani 1 1 d . . . . .
N1 N 0.23549(18) 0.50547(14) 0.45235(18) 0.0136(3) Uani 1 1 d . . . . .
C1 C 0.1570(2) 0.58470(17) 0.3459(2) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.2611(2) 0.64411(18) 0.2396(2) 0.0178(4) Uani 1 1 d . . . . .
H2A H 0.334016 0.703790 0.299557 0.021 Uiso 1 1 calc R U . . .
H2AB H 0.193083 0.691338 0.158489 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3603(2) 0.5489(2) 0.1618(2) 0.0194(4) Uani 1 1 d . . . . .
H3A H 0.304357 0.529584 0.057353 0.023 Uiso 1 1 calc R U . . .
H3AB H 0.464165 0.586614 0.149160 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3898(2) 0.42714(17) 0.2534(2) 0.0152(3) Uani 1 1 d . . . . .
H4 H 0.300000 0.369650 0.216234 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5453(2) 0.36180(17) 0.2255(2) 0.0174(4) Uani 1 1 d . . . . .
H5 H 0.550145 0.280738 0.281904 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6900(2) 0.43762(18) 0.2940(2) 0.0178(4) Uani 1 1 d . . . . .
H6A H 0.788530 0.393097 0.277738 0.021 Uiso 1 1 calc R U . . .
H6AB H 0.689255 0.518763 0.240459 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6889(2) 0.45880(19) 0.4665(2) 0.0181(4) Uani 1 1 d . . . . .
H7A H 0.779762 0.512903 0.506298 0.022 Uiso 1 1 calc R U . . .
H7AB H 0.704043 0.378042 0.520830 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5345(2) 0.51860(16) 0.5041(2) 0.0139(3) Uani 1 1 d . . . . .
H8 H 0.528647 0.604461 0.459859 0.017 Uiso 1 1 calc R U . . .
C9 C 0.3882(2) 0.44657(16) 0.4273(2) 0.0131(3) Uani 1 1 d . . . . .
C10 C 0.5464(3) 0.3326(2) 0.0542(3) 0.0289(5) Uani 1 1 d . . . . .
H10A H 0.450405 0.285580 0.014713 0.043 Uiso 1 1 calc R U . . .
H10B H 0.640887 0.283143 0.041904 0.043 Uiso 1 1 calc R U . . .
H10C H 0.548614 0.410377 -0.003874 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5410(2) 0.53026(19) 0.6793(2) 0.0209(4) Uani 1 1 d . . . . .
H11A H 0.622924 0.590795 0.718818 0.031 Uiso 1 1 calc R U . . .
H11B H 0.566905 0.449284 0.727629 0.031 Uiso 1 1 calc R U . . .
H11C H 0.437327 0.558162 0.703724 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2677(2) 0.32524(19) 0.6025(2) 0.0196(4) Uani 1 1 d . . . . .
H12A H 0.321473 0.342917 0.708214 0.024 Uiso 1 1 calc R U . . .
H12B H 0.214244 0.243472 0.602858 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1460(2) 0.42788(17) 0.5485(2) 0.0150(3) Uani 1 1 d . . . . .
H13 H 0.054107 0.389523 0.480954 0.018 Uiso 1 1 calc R U . . .
C14 C 0.0838(2) 0.49331(18) 0.6820(2) 0.0150(4) Uani 1 1 d . . . . .
C15 C 0.0829(2) 0.62185(18) 0.6988(2) 0.0183(4) Uani 1 1 d . . . . .
H15 H 0.129407 0.672977 0.628400 0.022 Uiso 1 1 calc R U . . .
C16 C 0.0139(3) 0.6758(2) 0.8187(2) 0.0230(4) Uani 1 1 d . . . . .
H16 H 0.012102 0.763720 0.828385 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0522(2) 0.6026(2) 0.9239(2) 0.0235(4) Uani 1 1 d . . . . .
H17 H -0.098816 0.639812 1.005548 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0495(3) 0.4743(2) 0.9089(2) 0.0239(4) Uani 1 1 d . . . . .
H18 H -0.094245 0.423430 0.980712 0.029 Uiso 1 1 calc R U . . .
C19 C 0.0181(2) 0.41988(19) 0.7893(2) 0.0192(4) Uani 1 1 d . . . . .
H19 H 0.019780 0.331937 0.780230 0.023 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 1.231(2) . ?
O2 C12 1.430(2) . ?
O2 C9 1.435(2) . ?
N1 C1 1.365(2) . ?
N1 C13 1.468(2) . ?
N1 C9 1.485(2) . ?
C1 C2 1.508(3) . ?
C2 C3 1.542(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.538(3) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.535(2) . ?
C4 C5 1.544(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.526(3) . ?
C5 C10 1.530(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.534(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C11 1.529(3) . ?
C8 C9 1.536(2) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.540(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.391(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 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
C12 O2 C9 110.21(14) . . ?
C1 N1 C13 120.20(15) . . ?
C1 N1 C9 121.32(15) . . ?
C13 N1 C9 111.81(14) . . ?
O1 C1 N1 122.25(18) . . ?
O1 C1 C2 123.36(17) . . ?
N1 C1 C2 114.33(16) . . ?
C1 C2 C3 112.98(16) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2AB 109.0 . . ?
C3 C2 H2AB 109.0 . . ?
H2A C2 H2AB 107.8 . . ?
C4 C3 C2 113.36(15) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3AB 108.9 . . ?
C2 C3 H3AB 108.9 . . ?
H3A C3 H3AB 107.7 . . ?
C9 C4 C3 112.09(15) . . ?
C9 C4 C5 110.02(15) . . ?
C3 C4 C5 112.78(15) . . ?
C9 C4 H4 107.2 . . ?
C3 C4 H4 107.2 . . ?
C5 C4 H4 107.2 . . ?
C6 C5 C10 112.37(17) . . ?
C6 C5 C4 110.68(15) . . ?
C10 C5 C4 111.62(17) . . ?
C6 C5 H5 107.3 . . ?
C10 C5 H5 107.3 . . ?
C4 C5 H5 107.3 . . ?
C7 C6 C5 110.68(15) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6AB 109.5 . . ?
C5 C6 H6AB 109.5 . . ?
H6A C6 H6AB 108.1 . . ?
C6 C7 C8 113.30(15) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7AB 108.9 . . ?
C8 C7 H7AB 108.9 . . ?
H7A C7 H7AB 107.7 . . ?
C11 C8 C7 109.52(15) . . ?
C11 C8 C9 113.19(15) . . ?
C7 C8 C9 110.89(15) . . ?
C11 C8 H8 107.7 . . ?
C7 C8 H8 107.7 . . ?
C9 C8 H8 107.7 . . ?
O2 C9 N1 103.62(14) . . ?
O2 C9 C4 106.77(14) . . ?
N1 C9 C4 109.28(14) . . ?
O2 C9 C8 111.17(14) . . ?
N1 C9 C8 112.88(14) . . ?
C4 C9 C8 112.59(15) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 106.02(15) . . ?
O2 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
N1 C13 C14 115.94(15) . . ?
N1 C13 C12 101.89(14) . . ?
C14 C13 C12 112.77(15) . . ?
N1 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C15 C14 C19 118.86(18) . . ?
C15 C14 C13 123.38(17) . . ?
C19 C14 C13 117.71(16) . . ?
C14 C15 C16 120.14(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.3(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.63(19) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_D59ZB10_0ma_a1
_database_code_depnum_ccdc_archive 'CCDC 2217477'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.1740(7)
_cell_length_b                   8.1207(9)
_cell_length_c                   32.235(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1616.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6917
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      30.47

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52659
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_av_R_equivalents  0.1293
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         31.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5291
_reflns_number_gt                3758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.981
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+1.8389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5291
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1A O 0.0723(5) 1.0085(3) 0.36947(8) 0.0285(6) Uani 1 1 d . . . . .
O2A O 0.5751(4) 0.6826(3) 0.39163(7) 0.0200(5) Uani 1 1 d . . . . .
N1A N 0.2449(4) 0.7623(3) 0.36899(8) 0.0179(5) Uani 1 1 d . . . . .
C1A C 0.1261(5) 0.8839(4) 0.38826(11) 0.0216(7) Uani 1 1 d . . . . .
C2A C 0.0646(6) 0.8581(5) 0.43310(11) 0.0260(7) Uani 1 1 d . . . . .
H1 H -0.069303 0.795745 0.434400 0.031 Uiso 1 1 calc R U . . .
H2 H 0.039149 0.964193 0.446016 0.031 Uiso 1 1 calc R U . . .
C3A C 0.2397(6) 0.7667(5) 0.45720(10) 0.0254(7) Uani 1 1 d . . . . .
H3 H 0.372521 0.830486 0.457496 0.030 Uiso 1 1 calc R U . . .
H4 H 0.193628 0.749188 0.485627 0.030 Uiso 1 1 calc R U . . .
C4A C 0.2770(6) 0.6030(4) 0.43587(10) 0.0210(7) Uani 1 1 d . . . . .
H4A H 0.135819 0.548152 0.434357 0.025 Uiso 1 1 calc R U . . .
C5A C 0.4318(6) 0.4821(4) 0.45714(10) 0.0230(7) Uani 1 1 d . . . . .
H5 H 0.577292 0.527236 0.456842 0.028 Uiso 1 1 calc R U . . .
H6 H 0.388662 0.468030 0.485859 0.028 Uiso 1 1 calc R U . . .
C6A C 0.4321(6) 0.3151(4) 0.43559(10) 0.0228(7) Uani 1 1 d . . . . .
H6A H 0.287226 0.267277 0.438570 0.027 Uiso 1 1 calc R U . . .
C7A C 0.4786(5) 0.3345(4) 0.38905(10) 0.0213(7) Uani 1 1 d . . . . .
H7 H 0.457391 0.228940 0.375582 0.026 Uiso 1 1 calc R U . . .
H8 H 0.629350 0.365126 0.385489 0.026 Uiso 1 1 calc R U . . .
C8A C 0.3361(5) 0.4634(4) 0.36738(10) 0.0188(6) Uani 1 1 d . . . . .
H8A H 0.395342 0.480985 0.339522 0.023 Uiso 1 1 calc R U . . .
C9A C 0.3536(5) 0.6273(4) 0.39106(9) 0.0168(6) Uani 1 1 d . . . . .
C10A C 0.6141(5) 0.7497(5) 0.35115(10) 0.0244(7) Uani 1 1 d . . . . .
H10A H 0.668580 0.665211 0.332604 0.029 Uiso 1 1 calc R U . . .
H10B H 0.719508 0.838087 0.352584 0.029 Uiso 1 1 calc R U . . .
C11A C 0.3918(5) 0.8160(4) 0.33550(9) 0.0202(7) Uani 1 1 d . . . . .
H11A H 0.397043 0.936655 0.335480 0.024 Uiso 1 1 calc R U . . .
C12A C 0.3339(6) 0.7580(4) 0.29194(10) 0.0207(7) Uani 1 1 d . . . . .
C13A C 0.4908(6) 0.7702(4) 0.26103(10) 0.0231(7) Uani 1 1 d . . . . .
H13A H 0.627232 0.811472 0.267442 0.028 Uiso 1 1 calc R U . . .
C14A C 0.4447(7) 0.7212(4) 0.22066(10) 0.0269(8) Uani 1 1 d . . . . .
H14A H 0.550507 0.729784 0.200232 0.032 Uiso 1 1 calc R U . . .
C15A C 0.2413(6) 0.6593(4) 0.21069(10) 0.0266(8) Uani 1 1 d . . . . .
H15A H 0.210822 0.625434 0.183754 0.032 Uiso 1 1 calc R U . . .
C16A C 0.0847(6) 0.6488(5) 0.24128(11) 0.0283(8) Uani 1 1 d . . . . .
H16A H -0.052195 0.608358 0.234848 0.034 Uiso 1 1 calc R U . . .
C17A C 0.1312(6) 0.6987(5) 0.28171(11) 0.0255(8) Uani 1 1 d . . . . .
H17A H 0.024521 0.691866 0.302012 0.031 Uiso 1 1 calc R U . . .
C18A C 0.5937(7) 0.1972(5) 0.45540(11) 0.0326(9) Uani 1 1 d . . . . .
H18A H 0.557950 0.182263 0.484133 0.049 Uiso 1 1 calc R U . . .
H18B H 0.737070 0.242101 0.453134 0.049 Uiso 1 1 calc R U . . .
H18C H 0.587961 0.092947 0.441403 0.049 Uiso 1 1 calc R U . . .
C19A C 0.1012(6) 0.4046(4) 0.36240(11) 0.0251(7) Uani 1 1 d . . . . .
H19A H 0.091492 0.331180 0.339144 0.038 Uiso 1 1 calc R U . . .
H19B H 0.008581 0.497875 0.357838 0.038 Uiso 1 1 calc R U . . .
H19C H 0.056486 0.348118 0.387123 0.038 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
O1A C1A 1.226(4) . ?
O2A C10A 1.435(4) . ?
O2A C9A 1.439(4) . ?
N1A C1A 1.378(4) . ?
N1A C9A 1.469(4) . ?
N1A C11A 1.476(4) . ?
C1A C2A 1.509(5) . ?
C2A C3A 1.524(5) . ?
C2A H1 0.9700 . ?
C2A H2 0.9700 . ?
C3A C4A 1.514(5) . ?
C3A H3 0.9700 . ?
C3A H4 0.9700 . ?
C4A C5A 1.532(5) . ?
C4A C9A 1.533(4) . ?
C4A H4A 0.9800 . ?
C5A C6A 1.523(5) . ?
C5A H5 0.9700 . ?
C5A H6 0.9700 . ?
C6A C18A 1.523(5) . ?
C6A C7A 1.535(4) . ?
C6A H6A 0.9800 . ?
C7A C8A 1.535(5) . ?
C7A H7 0.9700 . ?
C7A H8 0.9700 . ?
C8A C19A 1.535(5) . ?
C8A C9A 1.538(4) . ?
C8A H8A 0.9800 . ?
C10A C11A 1.559(5) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C12A 1.524(5) . ?
C11A H11A 0.9800 . ?
C12A C17A 1.381(5) . ?
C12A C13A 1.393(5) . ?
C13A C14A 1.390(5) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.390(5) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.384(5) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.395(5) . ?
C16A H16A 0.9300 . ?
C17A H17A 0.9300 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?

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
C10A O2A C9A 105.4(2) . . ?
C1A N1A C9A 124.0(3) . . ?
C1A N1A C11A 116.4(3) . . ?
C9A N1A C11A 107.1(2) . . ?
O1A C1A N1A 120.9(3) . . ?
O1A C1A C2A 121.3(3) . . ?
N1A C1A C2A 117.8(3) . . ?
C1A C2A C3A 112.2(3) . . ?
C1A C2A H1 109.2 . . ?
C3A C2A H1 109.2 . . ?
C1A C2A H2 109.2 . . ?
C3A C2A H2 109.2 . . ?
H1 C2A H2 107.9 . . ?
C4A C3A C2A 107.7(3) . . ?
C4A C3A H3 110.2 . . ?
C2A C3A H3 110.2 . . ?
C4A C3A H4 110.2 . . ?
C2A C3A H4 110.2 . . ?
H3 C3A H4 108.5 . . ?
C3A C4A C5A 117.0(3) . . ?
C3A C4A C9A 111.2(3) . . ?
C5A C4A C9A 108.2(3) . . ?
C3A C4A H4A 106.6 . . ?
C5A C4A H4A 106.6 . . ?
C9A C4A H4A 106.6 . . ?
C6A C5A C4A 111.5(3) . . ?
C6A C5A H5 109.3 . . ?
C4A C5A H5 109.3 . . ?
C6A C5A H6 109.3 . . ?
C4A C5A H6 109.3 . . ?
H5 C5A H6 108.0 . . ?
C18A C6A C5A 111.6(3) . . ?
C18A C6A C7A 110.6(3) . . ?
C5A C6A C7A 110.8(3) . . ?
C18A C6A H6A 107.9 . . ?
C5A C6A H6A 107.9 . . ?
C7A C6A H6A 107.9 . . ?
C6A C7A C8A 114.0(3) . . ?
C6A C7A H7 108.7 . . ?
C8A C7A H7 108.7 . . ?
C6A C7A H8 108.7 . . ?
C8A C7A H8 108.7 . . ?
H7 C7A H8 107.6 . . ?
C19A C8A C7A 112.2(3) . . ?
C19A C8A C9A 112.8(3) . . ?
C7A C8A C9A 108.9(3) . . ?
C19A C8A H8A 107.6 . . ?
C7A C8A H8A 107.6 . . ?
C9A C8A H8A 107.6 . . ?
O2A C9A N1A 102.0(2) . . ?
O2A C9A C4A 108.7(2) . . ?
N1A C9A C4A 114.3(3) . . ?
O2A C9A C8A 110.1(2) . . ?
N1A C9A C8A 111.9(2) . . ?
C4A C9A C8A 109.5(3) . . ?
O2A C10A C11A 106.1(2) . . ?
O2A C10A H10A 110.5 . . ?
C11A C10A H10A 110.5 . . ?
O2A C10A H10B 110.5 . . ?
C11A C10A H10B 110.5 . . ?
H10A C10A H10B 108.7 . . ?
N1A C11A C12A 116.0(3) . . ?
N1A C11A C10A 101.7(2) . . ?
C12A C11A C10A 113.4(3) . . ?
N1A C11A H11A 108.5 . . ?
C12A C11A H11A 108.5 . . ?
C10A C11A H11A 108.5 . . ?
C17A C12A C13A 119.0(3) . . ?
C17A C12A C11A 122.7(3) . . ?
C13A C12A C11A 118.3(3) . . ?
C14A C13A C12A 120.5(3) . . ?
C14A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C13A C14A C15A 120.3(3) . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A H14A 119.8 . . ?
C16A C15A C14A 119.3(3) . . ?
C16A C15A H15A 120.4 . . ?
C14A C15A H15A 120.4 . . ?
C15A C16A C17A 120.3(3) . . ?
C15A C16A H16A 119.9 . . ?
C17A C16A H16A 119.9 . . ?
C12A C17A C16A 120.7(3) . . ?
C12A C17A H17A 119.6 . . ?
C16A C17A H17A 119.6 . . ?
C6A C18A H18A 109.5 . . ?
C6A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C6A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C8A C19A H19A 109.5 . . ?
C8A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C8A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 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
C9A N1A C1A O1A 166.7(3) . . . . ?
C11A N1A C1A O1A 29.7(4) . . . . ?
C9A N1A C1A C2A -13.4(5) . . . . ?
C11A N1A C1A C2A -150.4(3) . . . . ?
O1A C1A C2A C3A -145.3(3) . . . . ?
N1A C1A C2A C3A 34.8(4) . . . . ?
C1A C2A C3A C4A -58.1(4) . . . . ?
C2A C3A C4A C5A -174.3(3) . . . . ?
C2A C3A C4A C9A 60.8(4) . . . . ?
C3A C4A C5A C6A 172.6(3) . . . . ?
C9A C4A C5A C6A -60.9(4) . . . . ?
C4A C5A C6A C18A 177.3(3) . . . . ?
C4A C5A C6A C7A 53.6(4) . . . . ?
C18A C6A C7A C8A -174.8(3) . . . . ?
C5A C6A C7A C8A -50.4(4) . . . . ?
C6A C7A C8A C19A -72.1(4) . . . . ?
C6A C7A C8A C9A 53.4(4) . . . . ?
C10A O2A C9A N1A -41.8(3) . . . . ?
C10A O2A C9A C4A -162.9(3) . . . . ?
C10A O2A C9A C8A 77.1(3) . . . . ?
C1A N1A C9A O2A -101.4(3) . . . . ?
C11A N1A C9A O2A 38.9(3) . . . . ?
C1A N1A C9A C4A 15.8(4) . . . . ?
C11A N1A C9A C4A 156.0(3) . . . . ?
C1A N1A C9A C8A 141.0(3) . . . . ?
C11A N1A C9A C8A -78.7(3) . . . . ?
C3A C4A C9A O2A 73.5(3) . . . . ?
C5A C4A C9A O2A -56.3(3) . . . . ?
C3A C4A C9A N1A -39.7(4) . . . . ?
C5A C4A C9A N1A -169.5(3) . . . . ?
C3A C4A C9A C8A -166.2(3) . . . . ?
C5A C4A C9A C8A 64.0(3) . . . . ?
C19A C8A C9A O2A -175.2(3) . . . . ?
C7A C8A C9A O2A 59.7(3) . . . . ?
C19A C8A C9A N1A -62.5(4) . . . . ?
C7A C8A C9A N1A 172.3(3) . . . . ?
C19A C8A C9A C4A 65.3(3) . . . . ?
C7A C8A C9A C4A -59.8(3) . . . . ?
C9A O2A C10A C11A 29.4(3) . . . . ?
C1A N1A C11A C12A -113.2(3) . . . . ?
C9A N1A C11A C12A 103.0(3) . . . . ?
C1A N1A C11A C10A 123.2(3) . . . . ?
C9A N1A C11A C10A -20.5(3) . . . . ?
O2A C10A C11A N1A -5.1(3) . . . . ?
O2A C10A C11A C12A -130.4(3) . . . . ?
N1A C11A C12A C17A 17.2(5) . . . . ?
C10A C11A C12A C17A 134.4(4) . . . . ?
N1A C11A C12A C13A -164.8(3) . . . . ?
C10A C11A C12A C13A -47.6(4) . . . . ?
C17A C12A C13A C14A -0.9(5) . . . . ?
C11A C12A C13A C14A -179.0(3) . . . . ?
C12A C13A C14A C15A 0.0(5) . . . . ?
C13A C14A C15A C16A 0.7(5) . . . . ?
C14A C15A C16A C17A -0.5(6) . . . . ?
C13A C12A C17A C16A 1.2(6) . . . . ?
C11A C12A C17A C16A 179.2(3) . . . . ?
C15A C16A C17A C12A -0.5(6) . . . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_I59ZB79_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217481'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.0011(14)
_cell_length_b                   11.0886(15)
_cell_length_c                   9.5396(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.404(7)
_cell_angle_gamma                90
_cell_volume                     816.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3906
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      29.77

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16724
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         30.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4969
_reflns_number_gt                3620
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.998

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0322P)²+0.2767P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4969
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.111
_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 0.1415(3) 0.30482(19) 0.5026(2) 0.0264(5) Uani 1 1 d . . . . .
O2 O 0.3243(3) 0.60769(18) 0.7645(2) 0.0219(4) Uani 1 1 d . . . . .
N1 N 0.3115(3) 0.4644(2) 0.5950(3) 0.0196(5) Uani 1 1 d . . . . .
C1 C 0.2638(4) 0.3457(3) 0.5978(3) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.3613(4) 0.2703(3) 0.7237(3) 0.0246(6) Uani 1 1 d . . . . .
H2A H 0.465559 0.235879 0.701579 0.029 Uiso 1 1 calc R U . . .
H2AB H 0.287062 0.202594 0.738436 0.029 Uiso 1 1 calc R U . . .
C3 C 0.4158(4) 0.3449(3) 0.8627(3) 0.0249(6) Uani 1 1 d . . . . .
H3A H 0.312390 0.378933 0.886658 0.030 Uiso 1 1 calc R U . . .
H3AB H 0.478664 0.293607 0.944767 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5329(4) 0.4459(2) 0.8371(3) 0.0217(6) Uani 1 1 d . . . . .
H4 H 0.626429 0.405846 0.802267 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6262(4) 0.5248(3) 0.9669(3) 0.0243(6) Uani 1 1 d . . . . .
H5 H 0.538083 0.576253 0.995577 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7530(4) 0.6070(3) 0.9177(3) 0.0280(7) Uani 1 1 d . . . . .
H6A H 0.847326 0.556911 0.899094 0.034 Uiso 1 1 calc R U . . .
H6AB H 0.805812 0.663245 0.997799 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6711(4) 0.6805(3) 0.7810(3) 0.0267(7) Uani 1 1 d . . . . .
H7A H 0.763960 0.722651 0.749354 0.032 Uiso 1 1 calc R U . . .
H7AB H 0.594229 0.742616 0.805021 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5655(4) 0.6029(3) 0.6545(3) 0.0217(6) Uani 1 1 d . . . . .
H8 H 0.496491 0.658865 0.578770 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4362(4) 0.5274(2) 0.7129(3) 0.0197(6) Uani 1 1 d . . . . .
C10 C 0.2002(4) 0.6533(3) 0.6380(3) 0.0249(6) Uani 1 1 d . . . . .
H10A H 0.243272 0.728233 0.603170 0.030 Uiso 1 1 calc R U . . .
H10B H 0.088425 0.670657 0.659880 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1782(4) 0.5515(3) 0.5218(3) 0.0210(6) Uani 1 1 d . . . . .
H11 H 0.062034 0.513420 0.510261 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1912(4) 0.5904(3) 0.3731(3) 0.0211(6) Uani 1 1 d . . . . .
C13 C 0.2604(4) 0.5111(3) 0.2893(3) 0.0260(6) Uani 1 1 d . . . . .
H13 H 0.305416 0.435444 0.328491 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2639(4) 0.5422(3) 0.1495(3) 0.0282(6) Uani 1 1 d . . . . .
H14 H 0.311923 0.487839 0.093706 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1977(4) 0.6522(3) 0.0903(3) 0.0272(6) Uani 1 1 d . . . . .
H15 H 0.200429 0.673423 -0.005487 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1274(4) 0.7306(3) 0.1726(3) 0.0243(6) Uani 1 1 d . . . . .
H16 H 0.081146 0.805822 0.132629 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1242(4) 0.7000(3) 0.3133(3) 0.0225(6) Uani 1 1 d . . . . .
H17 H 0.075882 0.754407 0.368812 0.027 Uiso 1 1 calc R U . . .
C18 C 0.7218(5) 0.4505(3) 1.0989(3) 0.0313(7) Uani 1 1 d . . . . .
H18A H 0.800691 0.393803 1.070086 0.047 Uiso 1 1 calc R U . . .
H18B H 0.637560 0.405486 1.136498 0.047 Uiso 1 1 calc R U . . .
H18C H 0.788505 0.504421 1.174667 0.047 Uiso 1 1 calc R U . . .
C19 C 0.6797(4) 0.5269(3) 0.5833(3) 0.0270(6) Uani 1 1 d . . . . .
H19A H 0.606841 0.471464 0.512908 0.040 Uiso 1 1 calc R U . . .
H19B H 0.762300 0.480438 0.658141 0.040 Uiso 1 1 calc R U . . .
H19C H 0.743189 0.579903 0.533317 0.040 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 1.231(3) . ?
O2 C10 1.436(3) . ?
O2 C9 1.439(3) . ?
N1 C1 1.373(4) . ?
N1 C9 1.467(4) . ?
N1 C11 1.470(4) . ?
C1 C2 1.501(4) . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.521(4) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.528(4) . ?
C4 C5 1.538(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.528(4) . ?
C5 C18 1.529(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.530(4) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.539(4) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C19 1.528(4) . ?
C8 C9 1.545(4) . ?
C8 H8 1.0000 . ?
C10 C11 1.559(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.512(4) . ?
C11 H11 1.0000 . ?
C12 C17 1.388(4) . ?
C12 C13 1.398(4) . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C10 O2 C9 106.5(2) . . ?
C1 N1 C9 125.3(2) . . ?
C1 N1 C11 118.0(2) . . ?
C9 N1 C11 108.1(2) . . ?
O1 C1 N1 120.6(3) . . ?
O1 C1 C2 121.9(3) . . ?
N1 C1 C2 117.5(2) . . ?
C1 C2 C3 111.2(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2AB 109.4 . . ?
C3 C2 H2AB 109.4 . . ?
H2A C2 H2AB 108.0 . . ?
C4 C3 C2 107.8(2) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3AB 110.1 . . ?
C2 C3 H3AB 110.1 . . ?
H3A C3 H3AB 108.5 . . ?
C3 C4 C9 110.7(2) . . ?
C3 C4 C5 118.6(2) . . ?
C9 C4 C5 109.0(2) . . ?
C3 C4 H4 105.9 . . ?
C9 C4 H4 105.9 . . ?
C5 C4 H4 105.9 . . ?
C6 C5 C18 110.3(3) . . ?
C6 C5 C4 108.2(2) . . ?
C18 C5 C4 112.7(2) . . ?
C6 C5 H5 108.5 . . ?
C18 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
C5 C6 C7 114.3(2) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6AB 108.7 . . ?
C7 C6 H6AB 108.7 . . ?
H6A C6 H6AB 107.6 . . ?
C6 C7 C8 113.1(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7AB 109.0 . . ?
C8 C7 H7AB 109.0 . . ?
H7A C7 H7AB 107.8 . . ?
C19 C8 C7 112.8(3) . . ?
C19 C8 C9 113.4(2) . . ?
C7 C8 C9 107.5(2) . . ?
C19 C8 H8 107.6 . . ?
C7 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
O2 C9 N1 101.5(2) . . ?
O2 C9 C4 109.5(2) . . ?
N1 C9 C4 114.5(2) . . ?
O2 C9 C8 109.0(2) . . ?
N1 C9 C8 111.5(2) . . ?
C4 C9 C8 110.5(2) . . ?
O2 C10 C11 105.4(2) . . ?
O2 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
O2 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
N1 C11 C12 114.2(2) . . ?
N1 C11 C10 102.0(2) . . ?
C12 C11 C10 116.0(2) . . ?
N1 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C10 C11 H11 108.1 . . ?
C17 C12 C13 118.9(3) . . ?
C17 C12 C11 121.3(3) . . ?
C13 C12 C11 119.6(3) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.4(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_d59zb89_0m
_database_code_depnum_ccdc_archive 'CCDC 2217479'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.2337(3)
_cell_length_b                   12.0198(3)
_cell_length_c                   15.9765(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1581.15(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      30.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15601
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.185
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4717
_reflns_number_gt                4496
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.987

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0531P)²+0.2471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 1874 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.37820(13) 0.66705(9) 0.45608(7) 0.0209(2) Uani 1 1 d . . . . .
O2 O 0.50366(11) 0.53867(8) 0.71291(6) 0.01352(19) Uani 1 1 d . . . . .
N1 N 0.42191(14) 0.61445(9) 0.58988(8) 0.0135(2) Uani 1 1 d . . . . .
C1 C 0.32469(17) 0.63083(11) 0.52253(9) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.14833(19) 0.59891(16) 0.53187(11) 0.0267(3) Uani 1 1 d . . . . .
H2A H 0.118616 0.553164 0.482674 0.032 Uiso 1 1 calc R U . . .
H2B H 0.083446 0.668119 0.528654 0.032 Uiso 1 1 calc R U . . .
C3 C 0.09358(18) 0.53571(13) 0.61019(10) 0.0196(3) Uani 1 1 d . . . . .
H3A H 0.027793 0.470897 0.592506 0.024 Uiso 1 1 calc R U . . .
H3B H 0.022422 0.585019 0.643637 0.024 Uiso 1 1 calc R U . . .
C4 C 0.23264(16) 0.49408(11) 0.66666(9) 0.0135(2) Uani 1 1 d . . . . .
H4 H 0.283191 0.428350 0.638490 0.016 Uiso 1 1 calc R U . . .
C5 C 0.17656(17) 0.45657(12) 0.75434(9) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.273935 0.425846 0.783748 0.020 Uiso 1 1 calc R U . . .
C6 C 0.11535(18) 0.55489(12) 0.80626(10) 0.0194(3) Uani 1 1 d . . . . .
H6A H 0.090417 0.529316 0.863743 0.023 Uiso 1 1 calc R U . . .
H6B H 0.013829 0.583914 0.781242 0.023 Uiso 1 1 calc R U . . .
C7 C 0.24202(18) 0.64847(12) 0.81008(9) 0.0177(3) Uani 1 1 d . . . . .
H7A H 0.337265 0.622425 0.842425 0.021 Uiso 1 1 calc R U . . .
H7B H 0.194922 0.713017 0.839956 0.021 Uiso 1 1 calc R U . . .
C8 C 0.29845(16) 0.68586(11) 0.72249(9) 0.0137(2) Uani 1 1 d . . . . .
H8 H 0.200560 0.713862 0.692013 0.016 Uiso 1 1 calc R U . . .
C9 C 0.36279(15) 0.58438(10) 0.67372(8) 0.0117(2) Uani 1 1 d . . . . .
C10 C 0.64609(16) 0.58461(12) 0.67452(9) 0.0158(3) Uani 1 1 d . . . . .
H10A H 0.737003 0.530797 0.676898 0.019 Uiso 1 1 calc R U . . .
H10B H 0.679498 0.653724 0.703497 0.019 Uiso 1 1 calc R U . . .
C11 C 0.59980(16) 0.60940(11) 0.58308(9) 0.0142(2) Uani 1 1 d . . . . .
H11 H 0.644043 0.683317 0.565600 0.017 Uiso 1 1 calc R U . . .
C12 C 0.65599(16) 0.51936(11) 0.52326(9) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.75383(17) 0.54603(13) 0.45526(10) 0.0183(3) Uani 1 1 d . . . . .
H13 H 0.779734 0.621661 0.444315 0.022 Uiso 1 1 calc R U . . .
C14 C 0.81438(19) 0.46295(14) 0.40294(10) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.882242 0.482058 0.357048 0.026 Uiso 1 1 calc R U . . .
C15 C 0.7756(2) 0.35248(14) 0.41786(11) 0.0258(3) Uani 1 1 d . . . . .
H15 H 0.817089 0.295753 0.382410 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6755(2) 0.32497(13) 0.48504(11) 0.0287(4) Uani 1 1 d . . . . .
H16 H 0.647601 0.249439 0.495043 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6165(2) 0.40769(13) 0.53730(11) 0.0237(3) Uani 1 1 d . . . . .
H17 H 0.548619 0.388362 0.583116 0.028 Uiso 1 1 calc R U . . .
C18 C 0.0503(2) 0.36371(13) 0.75051(11) 0.0231(3) Uani 1 1 d . . . . .
H18A H 0.027160 0.337186 0.807276 0.035 Uiso 1 1 calc R U . . .
H18B H 0.092469 0.302113 0.716697 0.035 Uiso 1 1 calc R U . . .
H18C H -0.049714 0.392199 0.725112 0.035 Uiso 1 1 calc R U . . .
C19 C 0.41787(18) 0.78240(12) 0.72906(10) 0.0189(3) Uani 1 1 d . . . . .
H19A H 0.506104 0.762291 0.767345 0.028 Uiso 1 1 calc R U . . .
H19B H 0.361412 0.848306 0.750454 0.028 Uiso 1 1 calc R U . . .
H19C H 0.462848 0.798668 0.673603 0.028 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 1.2291(18) . ?
O2 C9 1.4281(15) . ?
O2 C10 1.4341(16) . ?
N1 C1 1.3556(18) . ?
N1 C11 1.4699(17) . ?
N1 C9 1.4703(17) . ?
C1 C2 1.509(2) . ?
C2 C3 1.532(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.541(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.5294(18) . ?
C4 C5 1.542(2) . ?
C4 H4 1.0000 . ?
C5 C18 1.526(2) . ?
C5 C6 1.529(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.535(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.541(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C19 1.5246(19) . ?
C8 C9 1.5413(18) . ?
C8 H8 1.0000 . ?
C10 C11 1.5389(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5162(19) . ?
C11 H11 1.0000 . ?
C12 C13 1.3899(19) . ?
C12 C17 1.399(2) . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C9 O2 C10 109.18(9) . . ?
C1 N1 C11 122.39(12) . . ?
C1 N1 C9 124.29(11) . . ?
C11 N1 C9 112.78(11) . . ?
O1 C1 N1 121.70(13) . . ?
O1 C1 C2 121.36(13) . . ?
N1 C1 C2 116.91(12) . . ?
C1 C2 C3 119.35(13) . . ?
C1 C2 H2A 107.5 . . ?
C3 C2 H2A 107.5 . . ?
C1 C2 H2B 107.5 . . ?
C3 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?
C2 C3 C4 114.87(12) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
C9 C4 C3 109.47(11) . . ?
C9 C4 C5 110.50(11) . . ?
C3 C4 C5 113.83(11) . . ?
C9 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C18 C5 C6 111.25(12) . . ?
C18 C5 C4 112.42(12) . . ?
C6 C5 C4 111.43(11) . . ?
C18 C5 H5 107.1 . . ?
C6 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C5 C6 C7 111.34(11) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 112.48(11) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C19 C8 C9 114.55(11) . . ?
C19 C8 C7 110.72(12) . . ?
C9 C8 C7 109.38(11) . . ?
C19 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C7 C8 H8 107.3 . . ?
O2 C9 N1 103.01(10) . . ?
O2 C9 C4 109.17(10) . . ?
N1 C9 C4 109.83(11) . . ?
O2 C9 C8 111.22(10) . . ?
N1 C9 C8 112.32(10) . . ?
C4 C9 C8 110.99(10) . . ?
O2 C10 C11 106.15(10) . . ?
O2 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
O2 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
N1 C11 C12 112.34(11) . . ?
N1 C11 C10 100.64(11) . . ?
C12 C11 C10 112.62(11) . . ?
N1 C11 H11 110.3 . . ?
C12 C11 H11 110.3 . . ?
C10 C11 H11 110.3 . . ?
C13 C12 C17 118.76(13) . . ?
C13 C12 C11 120.33(13) . . ?
C17 C12 C11 120.86(13) . . ?
C12 C13 C14 120.70(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.03(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.75(15) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.07(15) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.68(15) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C11 N1 C1 O1 -16.8(2) . . . . ?
C9 N1 C1 O1 172.30(12) . . . . ?
C11 N1 C1 C2 161.24(14) . . . . ?
C9 N1 C1 C2 -9.7(2) . . . . ?
O1 C1 C2 C3 169.44(14) . . . . ?
N1 C1 C2 C3 -8.6(2) . . . . ?
C1 C2 C3 C4 -9.3(2) . . . . ?
C2 C3 C4 C9 41.75(17) . . . . ?
C2 C3 C4 C5 165.97(13) . . . . ?
C9 C4 C5 C18 -178.17(12) . . . . ?
C3 C4 C5 C18 58.16(16) . . . . ?
C9 C4 C5 C6 56.16(14) . . . . ?
C3 C4 C5 C6 -67.50(15) . . . . ?
C18 C5 C6 C7 -179.91(12) . . . . ?
C4 C5 C6 C7 -53.61(16) . . . . ?
C5 C6 C7 C8 54.03(16) . . . . ?
C6 C7 C8 C19 177.31(11) . . . . ?
C6 C7 C8 C9 -55.53(14) . . . . ?
C10 O2 C9 N1 25.72(12) . . . . ?
C10 O2 C9 C4 142.40(11) . . . . ?
C10 O2 C9 C8 -94.80(12) . . . . ?
C1 N1 C9 O2 160.07(11) . . . . ?
C11 N1 C9 O2 -11.63(14) . . . . ?
C1 N1 C9 C4 43.87(16) . . . . ?
C11 N1 C9 C4 -127.84(12) . . . . ?
C1 N1 C9 C8 -80.16(15) . . . . ?
C11 N1 C9 C8 108.13(12) . . . . ?
C3 C4 C9 O2 -169.48(11) . . . . ?
C5 C4 C9 O2 64.38(13) . . . . ?
C3 C4 C9 N1 -57.22(14) . . . . ?
C5 C4 C9 N1 176.63(10) . . . . ?
C3 C4 C9 C8 67.58(14) . . . . ?
C5 C4 C9 C8 -58.56(14) . . . . ?
C19 C8 C9 O2 60.96(15) . . . . ?
C7 C8 C9 O2 -64.00(13) . . . . ?
C19 C8 C9 N1 -53.90(15) . . . . ?
C7 C8 C9 N1 -178.86(11) . . . . ?
C19 C8 C9 C4 -177.29(12) . . . . ?
C7 C8 C9 C4 57.75(14) . . . . ?
C9 O2 C10 C11 -30.31(13) . . . . ?
C1 N1 C11 C12 -57.46(17) . . . . ?
C9 N1 C11 C12 114.43(12) . . . . ?
C1 N1 C11 C10 -177.48(11) . . . . ?
C9 N1 C11 C10 -5.59(14) . . . . ?
O2 C10 C11 N1 20.90(13) . . . . ?
O2 C10 C11 C12 -98.91(12) . . . . ?
N1 C11 C12 C13 122.92(14) . . . . ?
C10 C11 C12 C13 -124.29(14) . . . . ?
N1 C11 C12 C17 -59.87(18) . . . . ?
C10 C11 C12 C17 52.93(18) . . . . ?
C17 C12 C13 C14 -1.3(2) . . . . ?
C11 C12 C13 C14 175.98(13) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C13 C12 C17 C16 0.8(2) . . . . ?
C11 C12 C17 C16 -176.46(15) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_D59ZB2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217480'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.0138(5)
_cell_length_b                   6.3391(3)
_cell_length_c                   16.0011(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.122(2)
_cell_angle_gamma                90
_cell_volume                     811.65(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      30.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.139
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17964
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.701
_diffrn_reflns_theta_max         30.636
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4884
_reflns_number_gt                4752
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.985

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0539P)²+0.0989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 2095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4884
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 1.10725(12) 0.22018(17) 0.26316(6) 0.0209(2) Uani 1 1 d . . . . .
O2 O 0.83738(12) 0.76635(16) 0.20641(6) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.87812(13) 0.42776(18) 0.24623(7) 0.0147(2) Uani 1 1 d . . . . .
C1 C 0.99789(16) 0.2969(2) 0.21624(8) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.99092(18) 0.2531(2) 0.12319(8) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.913570 0.134176 0.110575 0.026 Uiso 1 1 calc R U . . .
H2B H 1.103300 0.210912 0.106512 0.026 Uiso 1 1 calc R U . . .
C3 C 0.93238(18) 0.4459(3) 0.07221(8) 0.0215(3) Uani 1 1 d . . . . .
H3A H 1.011751 0.564142 0.081987 0.026 Uiso 1 1 calc R U . . .
H3B H 0.926184 0.411868 0.011737 0.026 Uiso 1 1 calc R U . . .
C4 C 0.76084(16) 0.5068(2) 0.10015(8) 0.0170(2) Uani 1 1 d . . . . .
H4A H 0.688722 0.378773 0.092473 0.020 Uiso 1 1 calc R U . . .
C5 C 0.67126(19) 0.6845(2) 0.05152(9) 0.0223(3) Uani 1 1 d . . . . .
H5A H 0.669593 0.654477 -0.009238 0.027 Uiso 1 1 calc R U . . .
H5B H 0.731260 0.819251 0.062044 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4914(2) 0.7028(3) 0.07966(9) 0.0256(3) Uani 1 1 d . . . . .
H6A H 0.436417 0.825171 0.051281 0.031 Uiso 1 1 calc R U . . .
H6B H 0.428466 0.574530 0.062029 0.031 Uiso 1 1 calc R U . . .
C7 C 0.48353(18) 0.7297(2) 0.17453(9) 0.0227(3) Uani 1 1 d . . . . .
H7A H 0.536833 0.868340 0.189405 0.027 Uiso 1 1 calc R U . . .
C8 C 0.58454(16) 0.5580(2) 0.22340(8) 0.0159(2) Uani 1 1 d . . . . .
H8A H 0.590986 0.600655 0.283665 0.019 Uiso 1 1 calc R U . . .
C9 C 0.76512(16) 0.5609(2) 0.19333(8) 0.0145(2) Uani 1 1 d . . . . .
C10 C 0.88377(18) 0.7784(2) 0.29436(8) 0.0202(3) Uani 1 1 d . . . . .
H10A H 0.790277 0.834857 0.325592 0.024 Uiso 1 1 calc R U . . .
H10B H 0.982085 0.871349 0.304361 0.024 Uiso 1 1 calc R U . . .
C11 C 0.92610(16) 0.5491(2) 0.32262(8) 0.0159(2) Uani 1 1 d . . . . .
H11A H 1.049915 0.537898 0.333220 0.019 Uiso 1 1 calc R U . . .
C12 C 0.84342(16) 0.4806(2) 0.40094(8) 0.0175(2) Uani 1 1 d . . . . .
C13 C 0.76473(19) 0.2859(3) 0.40623(9) 0.0237(3) Uani 1 1 d . . . . .
H13A H 0.761136 0.193383 0.359475 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6911(2) 0.2252(3) 0.47935(10) 0.0326(4) Uani 1 1 d . . . . .
H14A H 0.636370 0.092623 0.482146 0.039 Uiso 1 1 calc R U . . .
C15 C 0.6980(2) 0.3587(4) 0.54795(10) 0.0353(4) Uani 1 1 d . . . . .
H15A H 0.647012 0.318062 0.597718 0.042 Uiso 1 1 calc R U . . .
C16 C 0.7788(2) 0.5511(4) 0.54426(9) 0.0333(4) Uani 1 1 d . . . . .
H16A H 0.784655 0.641501 0.591685 0.040 Uiso 1 1 calc R U . . .
C17 C 0.8516(2) 0.6121(3) 0.47095(9) 0.0255(3) Uani 1 1 d . . . . .
H17A H 0.907128 0.744234 0.468602 0.031 Uiso 1 1 calc R U . . .
C18 C 0.30339(19) 0.7415(3) 0.19950(10) 0.0282(3) Uani 1 1 d . . . . .
H18A H 0.244917 0.853985 0.167709 0.042 Uiso 1 1 calc R U . . .
H18B H 0.301410 0.771816 0.259500 0.042 Uiso 1 1 calc R U . . .
H18C H 0.247739 0.606454 0.187391 0.042 Uiso 1 1 calc R U . . .
C19 C 0.50636(17) 0.3382(2) 0.21841(10) 0.0217(3) Uani 1 1 d . . . . .
H19A H 0.462690 0.311130 0.161010 0.033 Uiso 1 1 calc R U . . .
H19B H 0.414929 0.330159 0.256535 0.033 Uiso 1 1 calc R U . . .
H19C H 0.591320 0.232424 0.234467 0.033 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 1.2233(16) . ?
O2 C9 1.4363(15) . ?
O2 C10 1.4379(16) . ?
N1 C1 1.3747(17) . ?
N1 C9 1.4714(16) . ?
N1 C11 1.4773(16) . ?
C1 C2 1.5125(18) . ?
C2 C3 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5185(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5262(19) . ?
C4 C9 1.5285(17) . ?
C4 H4A 1.0000 . ?
C5 C6 1.537(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.532(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C18 1.521(2) . ?
C7 C8 1.5435(19) . ?
C7 H7A 1.0000 . ?
C8 C19 1.5281(19) . ?
C8 C9 1.5497(18) . ?
C8 H8A 1.0000 . ?
C10 C11 1.554(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5127(18) . ?
C11 H11A 1.0000 . ?
C12 C13 1.390(2) . ?
C12 C17 1.3953(19) . ?
C13 C14 1.393(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C9 O2 C10 105.74(9) . . ?
C1 N1 C9 124.38(10) . . ?
C1 N1 C11 116.60(10) . . ?
C9 N1 C11 107.56(10) . . ?
O1 C1 N1 121.07(12) . . ?
O1 C1 C2 121.20(12) . . ?
N1 C1 C2 117.73(11) . . ?
C1 C2 C3 111.87(12) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 107.61(11) . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 C5 116.48(11) . . ?
C3 C4 C9 111.81(11) . . ?
C5 C4 C9 108.47(11) . . ?
C3 C4 H4A 106.5 . . ?
C5 C4 H4A 106.5 . . ?
C9 C4 H4A 106.5 . . ?
C4 C5 C6 109.19(11) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C7 C6 C5 112.86(12) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C18 C7 C6 110.90(12) . . ?
C18 C7 C8 112.38(12) . . ?
C6 C7 C8 112.00(12) . . ?
C18 C7 H7A 107.1 . . ?
C6 C7 H7A 107.1 . . ?
C8 C7 H7A 107.1 . . ?
C19 C8 C7 114.47(11) . . ?
C19 C8 C9 112.42(11) . . ?
C7 C8 C9 107.90(11) . . ?
C19 C8 H8A 107.2 . . ?
C7 C8 H8A 107.2 . . ?
C9 C8 H8A 107.2 . . ?
O2 C9 N1 101.86(9) . . ?
O2 C9 C4 109.45(10) . . ?
N1 C9 C4 114.40(11) . . ?
O2 C9 C8 109.94(10) . . ?
N1 C9 C8 111.76(10) . . ?
C4 C9 C8 109.18(10) . . ?
O2 C10 C11 106.02(10) . . ?
O2 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
O2 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
N1 C11 C12 115.47(11) . . ?
N1 C11 C10 101.73(10) . . ?
C12 C11 C10 114.27(11) . . ?
N1 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C13 C12 C17 118.89(13) . . ?
C13 C12 C11 121.72(12) . . ?
C17 C12 C11 119.34(13) . . ?
C12 C13 C14 120.72(15) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C15 C14 C13 119.76(17) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C16 C15 C14 120.22(15) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 119.95(16) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C12 120.44(17) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_D59YB89_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2217478'
loop_
_audit_author_name
_audit_author_address
'M. Font-Bardia'
;Universitat de Barcelona
Spain
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   13.0323(13)
_cell_length_b                   7.7488(6)
_cell_length_c                   16.1799(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.606(4)
_cell_angle_gamma                90
_cell_volume                     1626.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3446
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.01

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6649
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37613
_diffrn_reflns_av_unetI/netI     0.1399
_diffrn_reflns_av_R_equivalents  0.1209
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.110
_diffrn_reflns_theta_max         30.609
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9872
_reflns_number_gt                5240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.998

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0196(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         9872
_refine_ls_number_parameters     402
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.4086(2) 0.4409(4) 0.54168(17) 0.0303(7) Uani 1 1 d . . . . .
O2 O 0.0860(2) 0.3586(3) 0.42322(15) 0.0242(6) Uani 1 1 d . . . . .
N1 N 0.2580(2) 0.3767(4) 0.46626(18) 0.0218(7) Uani 1 1 d . . . . .
C1 C 0.3509(3) 0.4570(5) 0.4769(2) 0.0255(9) Uani 1 1 d . . . . .
C2 C 0.3787(3) 0.5584(6) 0.4040(2) 0.0287(9) Uani 1 1 d . . . . .
H2A H 0.403277 0.477760 0.362778 0.034 Uiso 1 1 calc R U . . .
H2AB H 0.436504 0.636564 0.422459 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2897(3) 0.6669(5) 0.3610(3) 0.0267(9) Uani 1 1 d . . . . .
H3A H 0.297419 0.787258 0.381259 0.032 Uiso 1 1 calc R U . . .
H3AB H 0.296339 0.668333 0.300596 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1809(3) 0.6042(5) 0.3746(2) 0.0236(9) Uani 1 1 d . . . . .
H4 H 0.159036 0.666290 0.424201 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1021(3) 0.6470(5) 0.3004(2) 0.0252(9) Uani 1 1 d . . . . .
H5A H 0.031677 0.631667 0.317422 0.030 Uiso 1 1 calc R U . . .
H5AB H 0.109843 0.769807 0.285325 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1135(3) 0.5357(5) 0.2242(2) 0.0263(9) Uani 1 1 d . . . . .
H6 H 0.181994 0.561501 0.204005 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1118(3) 0.3456(5) 0.2485(2) 0.0279(9) Uani 1 1 d . . . . .
H7A H 0.120668 0.273657 0.199152 0.033 Uiso 1 1 calc R U . . .
H7AB H 0.044006 0.317421 0.267805 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1973(3) 0.3023(5) 0.3174(2) 0.0239(9) Uani 1 1 d . . . . .
H8 H 0.264701 0.336362 0.297557 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1813(3) 0.4120(5) 0.3940(2) 0.0221(8) Uani 1 1 d . . . . .
C10 C 0.0971(3) 0.3675(6) 0.5123(2) 0.0284(9) Uani 1 1 d . . . . .
H10A H 0.047369 0.289837 0.536114 0.034 Uiso 1 1 calc R U . . .
H10B H 0.085979 0.486762 0.531477 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2081(3) 0.3094(5) 0.5374(2) 0.0251(9) Uani 1 1 d . . . . .
H11 H 0.234922 0.375625 0.587981 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2260(3) 0.1178(5) 0.5550(2) 0.0234(9) Uani 1 1 d . . . . .
C13 C 0.1511(3) 0.0128(5) 0.5835(2) 0.0276(10) Uani 1 1 d . . . . .
H13 H 0.083711 0.057255 0.586943 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1727(3) -0.1558(5) 0.6072(3) 0.0288(10) Uani 1 1 d . . . . .
H14 H 0.120296 -0.225900 0.626544 0.035 Uiso 1 1 calc R U . . .
C15 C 0.2703(3) -0.2227(5) 0.6027(2) 0.0280(10) Uani 1 1 d . . . . .
H15 H 0.285846 -0.337516 0.620243 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3450(3) -0.1206(5) 0.5723(3) 0.0308(10) Uani 1 1 d . . . . .
H16 H 0.411848 -0.166374 0.567656 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3229(3) 0.0488(6) 0.5487(2) 0.0293(10) Uani 1 1 d . . . . .
H17 H 0.374856 0.117928 0.527898 0.035 Uiso 1 1 calc R U . . .
C18 C 0.0292(3) 0.5762(6) 0.1538(3) 0.0367(11) Uani 1 1 d . . . . .
H18A H 0.033304 0.698158 0.138372 0.055 Uiso 1 1 calc R U . . .
H18B H -0.038619 0.552453 0.172583 0.055 Uiso 1 1 calc R U . . .
H18C H 0.039194 0.503929 0.105547 0.055 Uiso 1 1 calc R U . . .
C19 C 0.2011(4) 0.1089(5) 0.3353(3) 0.0319(10) Uani 1 1 d . . . . .
H19A H 0.135170 0.071662 0.353637 0.048 Uiso 1 1 calc R U . . .
H19B H 0.256724 0.084668 0.379008 0.048 Uiso 1 1 calc R U . . .
H19C H 0.213968 0.046306 0.284700 0.048 Uiso 1 1 calc R U . . .
O1A O 0.4312(2) 0.5645(4) 0.20717(17) 0.0316(7) Uani 1 1 d . . . . .
O2A O 0.5916(2) 1.0764(4) 0.20993(16) 0.0273(6) Uani 1 1 d . . . . .
N1A N 0.5139(3) 0.8155(4) 0.1823(2) 0.0240(8) Uani 1 1 d . . . . .
C1A C 0.5102(3) 0.6401(5) 0.1900(2) 0.0270(9) Uani 1 1 d . . . . .
C2A C 0.6056(3) 0.5445(6) 0.1713(3) 0.0352(10) Uani 1 1 d . . . . .
H2AA H 0.604414 0.531592 0.110375 0.042 Uiso 1 1 calc R U . . .
H2AC H 0.603335 0.427233 0.195382 0.042 Uiso 1 1 calc R U . . .
C3A C 0.7075(3) 0.6295(5) 0.2041(3) 0.0323(10) Uani 1 1 d . . . . .
H3AA H 0.738302 0.562651 0.252445 0.039 Uiso 1 1 calc R U . . .
H3AC H 0.755553 0.623187 0.160422 0.039 Uiso 1 1 calc R U . . .
C4A C 0.6976(3) 0.8179(5) 0.2301(2) 0.0282(10) Uani 1 1 d . . . . .
H4A H 0.678588 0.818337 0.288542 0.034 Uiso 1 1 calc R U . . .
C5A C 0.7994(3) 0.9184(6) 0.2293(3) 0.0328(10) Uani 1 1 d . . . . .
H5AA H 0.793196 1.029178 0.258887 0.039 Uiso 1 1 calc R U . . .
H5AC H 0.855428 0.851207 0.259978 0.039 Uiso 1 1 calc R U . . .
C6A C 0.8287(3) 0.9555(6) 0.1419(3) 0.0327(10) Uani 1 1 d . . . . .
H6A H 0.842760 0.842491 0.115326 0.039 Uiso 1 1 calc R U . . .
C7A C 0.7385(3) 1.0403(6) 0.0903(3) 0.0310(10) Uani 1 1 d . . . . .
H7AA H 0.726757 1.156032 0.113461 0.037 Uiso 1 1 calc R U . . .
H7AC H 0.757024 1.056219 0.032853 0.037 Uiso 1 1 calc R U . . .
C8A C 0.6386(3) 0.9377(6) 0.0873(2) 0.0245(9) Uani 1 1 d . . . . .
H8A H 0.652123 0.821603 0.063595 0.029 Uiso 1 1 calc R U . . .
C9A C 0.6116(3) 0.9098(5) 0.1765(2) 0.0233(9) Uani 1 1 d . . . . .
C10A C 0.5090(3) 1.0590(6) 0.2620(2) 0.0301(10) Uani 1 1 d . . . . .
H10C H 0.473386 1.170550 0.267560 0.036 Uiso 1 1 calc R U . . .
H10D H 0.535196 1.017263 0.317937 0.036 Uiso 1 1 calc R U . . .
C11A C 0.4371(3) 0.9273(5) 0.2174(2) 0.0256(9) Uani 1 1 d . . . . .
H11A H 0.403393 0.859674 0.259919 0.031 Uiso 1 1 calc R U . . .
C12A C 0.3542(3) 0.9937(5) 0.1535(2) 0.0261(10) Uani 1 1 d . . . . .
C13A C 0.3361(4) 1.1672(5) 0.1373(3) 0.0299(10) Uani 1 1 d . . . . .
H13A H 0.379039 1.251569 0.165796 0.036 Uiso 1 1 calc R U . . .
C14A C 0.2559(3) 1.2195(6) 0.0797(3) 0.0343(11) Uani 1 1 d . . . . .
H14A H 0.245432 1.338985 0.068885 0.041 Uiso 1 1 calc R U . . .
C15A C 0.1914(4) 1.1004(6) 0.0382(3) 0.0362(11) Uani 1 1 d . . . . .
H15A H 0.135839 1.137534 -0.000102 0.043 Uiso 1 1 calc R U . . .
C16A C 0.2084(4) 0.9264(6) 0.0528(3) 0.0378(11) Uani 1 1 d . . . . .
H16A H 0.165253 0.842917 0.023800 0.045 Uiso 1 1 calc R U . . .
C17A C 0.2888(3) 0.8742(6) 0.1100(3) 0.0318(10) Uani 1 1 d . . . . .
H17A H 0.299657 0.754498 0.119977 0.038 Uiso 1 1 calc R U . . .
C18A C 0.9260(3) 1.0634(6) 0.1444(3) 0.0433(12) Uani 1 1 d . . . . .
H18D H 0.945988 1.077176 0.087920 0.065 Uiso 1 1 calc R U . . .
H18E H 0.981587 1.005747 0.179030 0.065 Uiso 1 1 calc R U . . .
H18F H 0.913178 1.177189 0.167782 0.065 Uiso 1 1 calc R U . . .
C19A C 0.5530(3) 1.0217(6) 0.0305(2) 0.0307(10) Uani 1 1 d . . . . .
H19D H 0.574551 1.031250 -0.025706 0.046 Uiso 1 1 calc R U . . .
H19E H 0.538817 1.137057 0.051449 0.046 Uiso 1 1 calc R U . . .
H19F H 0.490514 0.951015 0.029069 0.046 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 1.235(5) . ?
O2 C9 1.432(4) . ?
O2 C10 1.436(4) . ?
N1 C1 1.358(5) . ?
N1 C11 1.472(5) . ?
N1 C9 1.487(5) . ?
C1 C2 1.491(5) . ?
C2 C3 1.542(6) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.535(5) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.522(5) . ?
C4 C5 1.538(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.524(5) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.526(5) . ?
C6 C18 1.536(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.534(5) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C19 1.526(5) . ?
C8 C9 1.533(5) . ?
C8 H8 1.0000 . ?
C10 C11 1.531(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.525(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.384(5) . ?
C12 C17 1.385(5) . ?
C13 C14 1.382(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O1A C1A 1.241(5) . ?
O2A C9A 1.433(5) . ?
O2A C10A 1.436(4) . ?
N1A C1A 1.366(5) . ?
N1A C11A 1.478(5) . ?
N1A C9A 1.478(5) . ?
C1A C2A 1.502(6) . ?
C2A C3A 1.530(6) . ?
C2A H2AA 0.9900 . ?
C2A H2AC 0.9900 . ?
C3A C4A 1.528(6) . ?
C3A H3AA 0.9900 . ?
C3A H3AC 0.9900 . ?
C4A C9A 1.526(5) . ?
C4A C5A 1.539(6) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.528(6) . ?
C5A H5AA 0.9900 . ?
C5A H5AC 0.9900 . ?
C6A C18A 1.516(6) . ?
C6A C7A 1.523(6) . ?
C6A H6A 1.0000 . ?
C7A C8A 1.522(5) . ?
C7A H7AA 0.9900 . ?
C7A H7AC 0.9900 . ?
C8A C19A 1.521(6) . ?
C8A C9A 1.534(5) . ?
C8A H8A 1.0000 . ?
C10A C11A 1.520(6) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C12A 1.510(6) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.386(6) . ?
C12A C17A 1.401(6) . ?
C13A C14A 1.390(6) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.378(6) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.383(6) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.389(6) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 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
C9 O2 C10 108.2(3) . . ?
C1 N1 C11 121.3(3) . . ?
C1 N1 C9 122.5(3) . . ?
C11 N1 C9 111.5(3) . . ?
O1 C1 N1 121.5(4) . . ?
O1 C1 C2 123.4(4) . . ?
N1 C1 C2 115.0(3) . . ?
C1 C2 C3 114.5(3) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2AB 108.6 . . ?
C3 C2 H2AB 108.6 . . ?
H2A C2 H2AB 107.6 . . ?
C4 C3 C2 115.3(3) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3AB 108.5 . . ?
C2 C3 H3AB 108.5 . . ?
H3A C3 H3AB 107.5 . . ?
C9 C4 C3 110.8(3) . . ?
C9 C4 C5 111.1(3) . . ?
C3 C4 C5 112.0(3) . . ?
C9 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C6 C5 C4 113.5(3) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5AB 108.9 . . ?
C4 C5 H5AB 108.9 . . ?
H5A C5 H5AB 107.7 . . ?
C5 C6 C7 109.4(3) . . ?
C5 C6 C18 111.4(3) . . ?
C7 C6 C18 111.2(3) . . ?
C5 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
C18 C6 H6 108.2 . . ?
C6 C7 C8 111.8(3) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7AB 109.3 . . ?
C8 C7 H7AB 109.3 . . ?
H7A C7 H7AB 107.9 . . ?
C19 C8 C9 113.3(3) . . ?
C19 C8 C7 111.1(3) . . ?
C9 C8 C7 108.6(3) . . ?
C19 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
O2 C9 N1 103.0(3) . . ?
O2 C9 C4 111.4(3) . . ?
N1 C9 C4 109.3(3) . . ?
O2 C9 C8 107.3(3) . . ?
N1 C9 C8 113.5(3) . . ?
C4 C9 C8 112.0(3) . . ?
O2 C10 C11 104.6(3) . . ?
O2 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
O2 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
N1 C11 C12 114.8(3) . . ?
N1 C11 C10 99.6(3) . . ?
C12 C11 C10 117.4(4) . . ?
N1 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C10 C11 H11 108.2 . . ?
C13 C12 C17 118.4(4) . . ?
C13 C12 C11 122.3(4) . . ?
C17 C12 C11 119.1(4) . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.7(4) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9A O2A C10A 108.1(3) . . ?
C1A N1A C11A 121.1(3) . . ?
C1A N1A C9A 122.4(4) . . ?
C11A N1A C9A 110.7(3) . . ?
O1A C1A N1A 121.9(4) . . ?
O1A C1A C2A 122.2(4) . . ?
N1A C1A C2A 115.8(4) . . ?
C1A C2A C3A 115.2(4) . . ?
C1A C2A H2AA 108.5 . . ?
C3A C2A H2AA 108.5 . . ?
C1A C2A H2AC 108.5 . . ?
C3A C2A H2AC 108.5 . . ?
H2AA C2A H2AC 107.5 . . ?
C4A C3A C2A 114.4(4) . . ?
C4A C3A H3AA 108.7 . . ?
C2A C3A H3AA 108.7 . . ?
C4A C3A H3AC 108.7 . . ?
C2A C3A H3AC 108.7 . . ?
H3AA C3A H3AC 107.6 . . ?
C9A C4A C3A 111.5(3) . . ?
C9A C4A C5A 110.2(3) . . ?
C3A C4A C5A 112.6(4) . . ?
C9A C4A H4A 107.4 . . ?
C3A C4A H4A 107.4 . . ?
C5A C4A H4A 107.4 . . ?
C6A C5A C4A 113.4(3) . . ?
C6A C5A H5AA 108.9 . . ?
C4A C5A H5AA 108.9 . . ?
C6A C5A H5AC 108.9 . . ?
C4A C5A H5AC 108.9 . . ?
H5AA C5A H5AC 107.7 . . ?
C18A C6A C7A 112.0(4) . . ?
C18A C6A C5A 111.3(4) . . ?
C7A C6A C5A 109.9(3) . . ?
C18A C6A H6A 107.8 . . ?
C7A C6A H6A 107.8 . . ?
C5A C6A H6A 107.8 . . ?
C8A C7A C6A 113.8(4) . . ?
C8A C7A H7AA 108.8 . . ?
C6A C7A H7AA 108.8 . . ?
C8A C7A H7AC 108.8 . . ?
C6A C7A H7AC 108.8 . . ?
H7AA C7A H7AC 107.7 . . ?
C19A C8A C7A 111.7(3) . . ?
C19A C8A C9A 114.0(3) . . ?
C7A C8A C9A 108.6(3) . . ?
C19A C8A H8A 107.4 . . ?
C7A C8A H8A 107.4 . . ?
C9A C8A H8A 107.4 . . ?
O2A C9A N1A 103.4(3) . . ?
O2A C9A C4A 110.9(3) . . ?
N1A C9A C4A 108.8(3) . . ?
O2A C9A C8A 107.2(3) . . ?
N1A C9A C8A 114.0(3) . . ?
C4A C9A C8A 112.2(3) . . ?
O2A C10A C11A 104.3(3) . . ?
O2A C10A H10C 110.9 . . ?
C11A C10A H10C 110.9 . . ?
O2A C10A H10D 110.9 . . ?
C11A C10A H10D 110.9 . . ?
H10C C10A H10D 108.9 . . ?
N1A C11A C12A 113.8(3) . . ?
N1A C11A C10A 99.6(3) . . ?
C12A C11A C10A 117.5(4) . . ?
N1A C11A H11A 108.5 . . ?
C12A C11A H11A 108.5 . . ?
C10A C11A H11A 108.5 . . ?
C13A C12A C17A 117.5(4) . . ?
C13A C12A C11A 123.9(4) . . ?
C17A C12A C11A 118.5(4) . . ?
C12A C13A C14A 120.8(4) . . ?
C12A C13A H13A 119.6 . . ?
C14A C13A H13A 119.6 . . ?
C15A C14A C13A 121.0(4) . . ?
C15A C14A H14A 119.5 . . ?
C13A C14A H14A 119.5 . . ?
C14A C15A C16A 119.3(4) . . ?
C14A C15A H15A 120.4 . . ?
C16A C15A H15A 120.4 . . ?
C15A C16A C17A 119.7(5) . . ?
C15A C16A H16A 120.2 . . ?
C17A C16A H16A 120.2 . . ?
C16A C17A C12A 121.7(4) . . ?
C16A C17A H17A 119.2 . . ?
C12A C17A H17A 119.2 . . ?
C6A C18A H18D 109.5 . . ?
C6A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C6A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C8A C19A H19D 109.5 . . ?
C8A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C8A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.070

