# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cb62
_database_code_depnum_ccdc_archive 'CCDC 2072225'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR Istituto di Chimica dei Composti Organometallici
Italy
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_formula_moiety         'C23 H25 N O3'
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44

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                   9.6415(7)
_cell_length_b                   9.7108(8)
_cell_length_c                   11.1357(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.262(1)
_cell_angle_gamma                90
_cell_volume                     1034.24(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2080
_cell_measurement_theta_min      5.27
_cell_measurement_theta_max      43.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            8352
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         28.762
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4719
_reflns_number_gt                2967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.820
_reflns_Friedel_fraction_full    0.967

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²+0.0321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4719
_refine_ls_number_parameters     254
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1804
_refine_ls_wR_factor_gt          0.1572
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.6933(3) 0.2812(3) 0.1948(3) 0.0571(8) Uani 1 1 d . . . . .
H1 H 0.739235 0.248971 0.273258 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6842(3) 0.4367(3) 0.2004(3) 0.0547(8) Uani 1 1 d . . . . .
C3 C 0.5787(4) 0.5088(4) 0.1320(3) 0.0658(9) Uani 1 1 d . . . . .
O1 O 0.4789(3) 0.4452(3) 0.0528(3) 0.0878(8) Uani 1 1 d D . . . .
H1O H 0.483(6) 0.353(6) 0.082(5) 0.132 Uiso 1 1 d D U . . .
C4 C 0.5695(5) 0.6519(5) 0.1389(4) 0.0794(11) Uani 1 1 d . . . . .
H4 H 0.496097 0.697279 0.093035 0.095 Uiso 1 1 calc R U . . .
C5 C 0.6633(5) 0.7241(4) 0.2095(4) 0.0874(13) Uani 1 1 d . . . . .
H5 H 0.653648 0.819201 0.213244 0.105 Uiso 1 1 calc R U . . .
C6 C 0.7780(5) 0.6601(4) 0.2795(3) 0.0739(11) Uani 1 1 d . . . . .
C7 C 0.8815(6) 0.7353(5) 0.3516(4) 0.1001(15) Uani 1 1 d . . . . .
H7 H 0.873519 0.830573 0.355429 0.120 Uiso 1 1 calc R U . . .
C8 C 0.9919(7) 0.6729(6) 0.4152(5) 0.1093(17) Uani 1 1 d . . . . .
H8 H 1.059257 0.725136 0.462037 0.131 Uiso 1 1 calc R U . . .
C9 C 1.0057(5) 0.5278(6) 0.4111(4) 0.0966(14) Uani 1 1 d . . . . .
H9 H 1.082055 0.484689 0.454899 0.116 Uiso 1 1 calc R U . . .
C10 C 0.9062(4) 0.4514(4) 0.3423(3) 0.0716(10) Uani 1 1 d . . . . .
H10 H 0.916197 0.356252 0.340198 0.086 Uiso 1 1 calc R U . . .
C11 C 0.7889(4) 0.5130(3) 0.2744(3) 0.0593(8) Uani 1 1 d . . . . .
C12 C 0.7761(3) 0.2262(4) 0.0974(3) 0.0659(9) Uani 1 1 d D . . . .
C13 C 0.7940(4) 0.3003(5) -0.0039(4) 0.0833(12) Uani 1 1 d D . . . .
H13 H 0.760130 0.389857 -0.012688 0.100 Uiso 1 1 calc R U . . .
C14 C 0.8627(6) 0.2418(8) -0.0936(5) 0.1139(18) Uani 1 1 d D . . . .
H14 H 0.875432 0.294057 -0.161358 0.137 Uiso 1 1 calc R U . . .
C15 C 0.9105(7) 0.1146(9) -0.0859(7) 0.134(3) Uani 1 1 d D . . . .
H15 H 0.955582 0.077808 -0.147663 0.161 Uiso 1 1 calc R U . . .
C16 C 0.8933(6) 0.0382(7) 0.0122(9) 0.139(3) Uani 1 1 d D . . . .
H16 H 0.925630 -0.052128 0.017378 0.167 Uiso 1 1 calc R U . . .
C17 C 0.8264(4) 0.0943(5) 0.1080(5) 0.0972(14) Uani 1 1 d D . . . .
H17 H 0.816890 0.042336 0.176637 0.117 Uiso 1 1 calc R U . . .
N1 N 0.5512(3) 0.2186(4) 0.1751(3) 0.0678(8) Uani 1 1 d . . . . .
H1N H 0.553(4) 0.139(5) 0.147(3) 0.072(12) Uiso 1 1 d . . . . .
C18 C 0.4788(4) 0.2148(5) 0.2816(4) 0.0771(10) Uani 1 1 d . . . . .
H18 H 0.463481 0.309681 0.306977 0.093 Uiso 1 1 calc R U . . .
C19 C 0.3333(5) 0.1435(9) 0.2504(6) 0.139(2) Uani 1 1 d . . . . .
H19 H 0.351188 0.053117 0.216215 0.166 Uiso 1 1 calc R U . . .
C20 C 0.2605(9) 0.1177(15) 0.3575(8) 0.226(6) Uani 1 1 d . . . . .
H20A H 0.266409 0.198372 0.407728 0.338 Uiso 1 1 calc R U . . .
H20B H 0.303825 0.041553 0.402630 0.338 Uiso 1 1 calc R U . . .
H20C H 0.164121 0.096616 0.331521 0.338 Uiso 1 1 calc R U . . .
C21 C 0.2416(7) 0.2211(14) 0.1535(9) 0.205(5) Uani 1 1 d . . . . .
H21A H 0.154220 0.173587 0.134983 0.308 Uiso 1 1 calc R U . . .
H21B H 0.287450 0.226912 0.082018 0.308 Uiso 1 1 calc R U . . .
H21C H 0.224831 0.312158 0.181936 0.308 Uiso 1 1 calc R U . . .
C22 C 0.5609(5) 0.1399(5) 0.3854(4) 0.0885(13) Uani 1 1 d . . . . .
O2 O 0.6335(5) 0.0405(4) 0.3767(4) 0.1277(14) Uani 1 1 d . . . . .
O3 O 0.5462(4) 0.1961(5) 0.4892(3) 0.1189(13) Uani 1 1 d . . . . .
C23 C 0.6067(9) 0.1245(13) 0.5974(6) 0.189(4) Uani 1 1 d . . . . .
H23A H 0.548817 0.047297 0.611924 0.284 Uiso 1 1 calc R U . . .
H23B H 0.612672 0.186152 0.665267 0.284 Uiso 1 1 calc R U . . .
H23C H 0.698564 0.092547 0.586840 0.284 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
C1 N1 1.490(4) . ?
C1 C2 1.514(5) . ?
C1 C12 1.523(4) . ?
C2 C3 1.381(5) . ?
C2 C11 1.427(5) . ?
C3 O1 1.368(5) . ?
C3 C4 1.395(6) . ?
C4 C5 1.322(6) . ?
C5 C6 1.413(6) . ?
C6 C7 1.403(6) . ?
C6 C11 1.434(5) . ?
C7 C8 1.347(8) . ?
C8 C9 1.416(8) . ?
C9 C10 1.368(6) . ?
C10 C11 1.411(5) . ?
C12 C13 1.367(6) . ?
C12 C17 1.369(6) . ?
C13 C14 1.389(6) . ?
C14 C15 1.317(10) . ?
C15 C16 1.348(11) . ?
C16 C17 1.424(9) . ?
N1 C18 1.451(5) . ?
C18 C22 1.504(6) . ?
C18 C19 1.564(7) . ?
C19 C20 1.479(9) . ?
C19 C21 1.507(11) . ?
C22 O2 1.204(5) . ?
C22 O3 1.302(6) . ?
O3 C23 1.449(8) . ?

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
N1 C1 C2 110.9(3) . . ?
N1 C1 C12 107.9(3) . . ?
C2 C1 C12 114.7(3) . . ?
C3 C2 C11 118.2(3) . . ?
C3 C2 C1 121.7(3) . . ?
C11 C2 C1 120.0(3) . . ?
O1 C3 C2 122.4(3) . . ?
O1 C3 C4 116.2(3) . . ?
C2 C3 C4 121.5(4) . . ?
C5 C4 C3 121.1(4) . . ?
C4 C5 C6 121.6(4) . . ?
C7 C6 C5 122.4(4) . . ?
C7 C6 C11 119.4(4) . . ?
C5 C6 C11 118.2(4) . . ?
C8 C7 C6 121.7(5) . . ?
C7 C8 C9 120.1(5) . . ?
C10 C9 C8 119.7(5) . . ?
C9 C10 C11 121.9(4) . . ?
C10 C11 C2 123.4(3) . . ?
C10 C11 C6 117.3(4) . . ?
C2 C11 C6 119.3(3) . . ?
C13 C12 C17 118.9(4) . . ?
C13 C12 C1 122.4(3) . . ?
C17 C12 C1 118.6(4) . . ?
C12 C13 C14 120.0(5) . . ?
C15 C14 C13 122.1(6) . . ?
C14 C15 C16 119.4(6) . . ?
C15 C16 C17 120.7(6) . . ?
C12 C17 C16 118.8(6) . . ?
C18 N1 C1 114.8(3) . . ?
N1 C18 C22 112.3(3) . . ?
N1 C18 C19 109.9(4) . . ?
C22 C18 C19 109.1(4) . . ?
C20 C19 C21 111.5(6) . . ?
C20 C19 C18 113.5(6) . . ?
C21 C19 C18 111.5(6) . . ?
O2 C22 O3 122.5(5) . . ?
O2 C22 C18 125.5(4) . . ?
O3 C22 C18 111.9(4) . . ?
C22 O3 C23 117.4(5) . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.191
_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_tc5
_database_code_depnum_ccdc_archive 'CCDC 2072228'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR Istituto di Chimica dei Composti Organometallici
Italy
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_formula_moiety         'C23 H24 Cl N O3'
_chemical_formula_sum            'C23 H24 Cl N O3'
_chemical_formula_weight         397.88

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'
Cl Cl 0.1484 0.1585 '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                   9.5094(5)
_cell_length_b                   18.3294(9)
_cell_length_c                   12.3185(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.750(1)
_cell_angle_gamma                90
_cell_volume                     2132.25(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5965
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      42.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            17187
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.665
_diffrn_reflns_theta_max         28.749
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             9787
_reflns_number_gt                7310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.836
_reflns_Friedel_fraction_full    0.966

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 2713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(19)
_chemical_absolute_configuration sym
_refine_ls_number_reflns         9787
_refine_ls_number_parameters     523
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.017
_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
C101 C 0.3337(3) 0.53057(17) 0.8844(2) 0.0555(7) Uani 1 1 d . . . . .
H101 H 0.385114 0.547945 0.825014 0.067 Uiso 1 1 calc R U . . .
C102 C 0.2651(3) 0.59585(16) 0.9314(2) 0.0579(7) Uani 1 1 d . . . . .
C103 C 0.2379(4) 0.5972(2) 1.0393(3) 0.0743(9) Uani 1 1 d . . . . .
O101 O 0.2721(4) 0.54072(16) 1.1090(2) 0.0974(9) Uani 1 1 d . . . . .
H12O H 0.338(6) 0.508(3) 1.080(5) 0.146 Uiso 1 1 d . U . . .
C104 C 0.1716(5) 0.6576(2) 1.0823(4) 0.0945(13) Uani 1 1 d . . . . .
H104 H 0.153176 0.657151 1.154805 0.113 Uiso 1 1 calc R U . . .
C105 C 0.1349(5) 0.7159(2) 1.0189(4) 0.0919(12) Uani 1 1 d . . . . .
H105 H 0.093917 0.755902 1.049292 0.110 Uiso 1 1 calc R U . . .
C106 C 0.1568(4) 0.71810(19) 0.9079(3) 0.0741(9) Uani 1 1 d . . . . .
C107 C 0.1216(4) 0.7791(2) 0.8422(4) 0.0907(12) Uani 1 1 d . . . . .
H107 H 0.084189 0.820101 0.872748 0.109 Uiso 1 1 calc R U . . .
C108 C 0.1410(5) 0.7798(2) 0.7345(4) 0.0958(13) Uani 1 1 d . . . . .
H108 H 0.116305 0.820907 0.692295 0.115 Uiso 1 1 calc R U . . .
C109 C 0.1974(5) 0.7194(2) 0.6877(3) 0.0857(11) Uani 1 1 d . . . . .
H109 H 0.209461 0.719785 0.613904 0.103 Uiso 1 1 calc R U . . .
C110 C 0.2354(4) 0.65904(19) 0.7501(3) 0.0681(9) Uani 1 1 d . . . . .
H110 H 0.272243 0.618685 0.717430 0.082 Uiso 1 1 calc R U . . .
C111 C 0.2203(3) 0.65659(17) 0.8624(3) 0.0589(7) Uani 1 1 d . . . . .
C112 C 0.2294(3) 0.47266(16) 0.8377(2) 0.0529(6) Uani 1 1 d D . . . .
C113 C 0.0901(3) 0.46962(18) 0.8606(3) 0.0657(8) Uani 1 1 d D . . . .
H113 H 0.056891 0.505565 0.904373 0.079 Uiso 1 1 calc R U . . .
C114 C -0.0002(3) 0.41459(18) 0.8202(3) 0.0690(8) Uani 1 1 d D . . . .
H114 H -0.093697 0.413902 0.835447 0.083 Uiso 1 1 calc R U . . .
C115 C 0.0498(3) 0.36066(17) 0.7568(3) 0.0628(8) Uani 1 1 d D . . . .
Cl11 Cl -0.06085(11) 0.28996(6) 0.70641(9) 0.0905(3) Uani 1 1 d . . . . .
C116 C 0.1871(3) 0.36229(18) 0.7316(3) 0.0650(8) Uani 1 1 d D . . . .
H116 H 0.220006 0.326012 0.688232 0.078 Uiso 1 1 calc R U . . .
C117 C 0.2752(3) 0.41824(17) 0.7714(2) 0.0627(8) Uani 1 1 d D . . . .
H117 H 0.367508 0.419672 0.753536 0.075 Uiso 1 1 calc R U . . .
N101 N 0.4382(3) 0.49552(16) 0.9678(2) 0.0601(6) Uani 1 1 d . . . . .
H11N H 0.456(4) 0.450(2) 0.944(3) 0.072 Uiso 1 1 d . U . . .
C118 C 0.5742(3) 0.53346(19) 0.9875(3) 0.0632(8) Uani 1 1 d . . . . .
H118 H 0.558474 0.582292 1.016094 0.076 Uiso 1 1 calc R U . . .
C119 C 0.6764(4) 0.4905(3) 1.0737(3) 0.0881(11) Uani 1 1 d . . . . .
H119 H 0.693918 0.442470 1.043007 0.106 Uiso 1 1 calc R U . . .
C120 C 0.6132(5) 0.4790(3) 1.1791(4) 0.1070(14) Uani 1 1 d . . . . .
H12D H 0.684230 0.459991 1.233601 0.161 Uiso 1 1 calc R U . . .
H12E H 0.536071 0.445072 1.167222 0.161 Uiso 1 1 calc R U . . .
H12F H 0.579055 0.524731 1.203684 0.161 Uiso 1 1 calc R U . . .
C121 C 0.8174(5) 0.5304(4) 1.0943(4) 0.129(2) Uani 1 1 d . . . . .
H12A H 0.800961 0.580518 1.111580 0.193 Uiso 1 1 calc R U . . .
H12B H 0.865294 0.527918 1.030024 0.193 Uiso 1 1 calc R U . . .
H12C H 0.874952 0.507905 1.154407 0.193 Uiso 1 1 calc R U . . .
C122 C 0.6437(3) 0.5408(2) 0.8831(3) 0.0688(9) Uani 1 1 d . . . . .
O102 O 0.6520(3) 0.49243(17) 0.8194(2) 0.0931(8) Uani 1 1 d . . . . .
O103 O 0.6958(3) 0.60706(16) 0.8727(3) 0.0970(8) Uani 1 1 d . . . . .
C123 C 0.7703(6) 0.6196(4) 0.7779(5) 0.134(2) Uani 1 1 d . . . . .
H12G H 0.836717 0.580824 0.771782 0.201 Uiso 1 1 calc R U . . .
H12H H 0.820009 0.665242 0.786195 0.201 Uiso 1 1 calc R U . . .
H12I H 0.703399 0.621105 0.713234 0.201 Uiso 1 1 calc R U . . .
C201 C 0.2838(3) 0.36457(16) 0.3656(2) 0.0518(6) Uani 1 1 d . . . . .
H201 H 0.183322 0.353648 0.368125 0.062 Uiso 1 1 calc R U . . .
C202 C 0.3672(3) 0.32756(17) 0.4636(2) 0.0533(6) Uani 1 1 d . . . . .
C203 C 0.4963(3) 0.3554(2) 0.5075(3) 0.0671(8) Uani 1 1 d . . . . .
O201 O 0.5566(2) 0.41421(17) 0.4658(3) 0.0930(9) Uani 1 1 d . . . . .
H22O H 0.491(6) 0.441(3) 0.432(5) 0.139 Uiso 1 1 d . U . . .
C204 C 0.5712(4) 0.3235(2) 0.6013(3) 0.0812(10) Uani 1 1 d . . . . .
H204 H 0.656728 0.343827 0.631137 0.097 Uiso 1 1 calc R U . . .
C205 C 0.5216(4) 0.2646(2) 0.6480(3) 0.0752(10) Uani 1 1 d . . . . .
H205 H 0.572272 0.244950 0.710350 0.090 Uiso 1 1 calc R U . . .
C206 C 0.3927(4) 0.23178(18) 0.6038(3) 0.0635(8) Uani 1 1 d . . . . .
C207 C 0.3386(5) 0.1696(2) 0.6531(3) 0.0765(10) Uani 1 1 d . . . . .
H207 H 0.389481 0.149185 0.714812 0.092 Uiso 1 1 calc R U . . .
C208 C 0.2158(6) 0.1398(2) 0.6121(3) 0.0914(13) Uani 1 1 d . . . . .
H208 H 0.180186 0.099879 0.646686 0.110 Uiso 1 1 calc R U . . .
C209 C 0.1398(5) 0.1686(2) 0.5169(3) 0.0843(11) Uani 1 1 d . . . . .
H209 H 0.056066 0.146383 0.487331 0.101 Uiso 1 1 calc R U . . .
C210 C 0.1876(4) 0.22866(18) 0.4674(3) 0.0644(8) Uani 1 1 d . . . . .
H210 H 0.135518 0.247158 0.404803 0.077 Uiso 1 1 calc R U . . .
C211 C 0.3147(3) 0.26316(16) 0.5096(2) 0.0536(7) Uani 1 1 d . . . . .
C212 C 0.3225(3) 0.33828(15) 0.2558(2) 0.0530(7) Uani 1 1 d D . . . .
C213 C 0.4422(4) 0.2980(2) 0.2456(3) 0.0750(9) Uani 1 1 d D . . . .
H213 H 0.502864 0.286274 0.307993 0.090 Uiso 1 1 calc R U . . .
C214 C 0.4742(4) 0.2747(2) 0.1455(3) 0.0860(11) Uani 1 1 d D . . . .
H214 H 0.557042 0.248681 0.139985 0.103 Uiso 1 1 calc R U . . .
C215 C 0.3834(4) 0.2900(2) 0.0541(3) 0.0760(9) Uani 1 1 d D . . . .
Cl21 Cl 0.42262(19) 0.25876(9) -0.07181(9) 0.1340(6) Uani 1 1 d . . . . .
C216 C 0.2633(4) 0.3306(2) 0.0603(3) 0.0764(10) Uani 1 1 d D . . . .
H216 H 0.202689 0.341610 -0.002335 0.092 Uiso 1 1 calc R U . . .
C217 C 0.2345(3) 0.35466(19) 0.1616(2) 0.0655(8) Uani 1 1 d D . . . .
H217 H 0.153812 0.382588 0.166505 0.079 Uiso 1 1 calc R U . . .
N201 N 0.3012(2) 0.44534(13) 0.3731(2) 0.0511(5) Uani 1 1 d . . . . .
H21N H 0.269(3) 0.4671(18) 0.307(3) 0.061 Uiso 1 1 d . U . . .
C218 C 0.2269(3) 0.47781(16) 0.4597(2) 0.0491(6) Uani 1 1 d . . . . .
H218 H 0.258773 0.451848 0.527680 0.059 Uiso 1 1 calc R U . . .
C219 C 0.2629(3) 0.55895(17) 0.4791(2) 0.0590(7) Uani 1 1 d . . . . .
H219 H 0.204939 0.576229 0.534608 0.071 Uiso 1 1 calc R U . . .
C220 C 0.2232(5) 0.60532(19) 0.3775(3) 0.0789(10) Uani 1 1 d . . . . .
H22A H 0.239258 0.655851 0.395334 0.118 Uiso 1 1 calc R U . . .
H22B H 0.125023 0.598008 0.351524 0.118 Uiso 1 1 calc R U . . .
H22C H 0.280276 0.591329 0.321663 0.118 Uiso 1 1 calc R U . . .
C221 C 0.4166(4) 0.5711(2) 0.5249(3) 0.0845(11) Uani 1 1 d . . . . .
H22G H 0.476731 0.560627 0.469493 0.127 Uiso 1 1 calc R U . . .
H22H H 0.440637 0.539511 0.586396 0.127 Uiso 1 1 calc R U . . .
H22I H 0.429548 0.621013 0.547757 0.127 Uiso 1 1 calc R U . . .
C222 C 0.0679(3) 0.46761(15) 0.4375(2) 0.0515(6) Uani 1 1 d . . . . .
O202 O 0.0041(2) 0.45531(14) 0.35004(19) 0.0728(6) Uani 1 1 d . . . . .
O203 O 0.0086(2) 0.47466(14) 0.52901(18) 0.0711(6) Uani 1 1 d . . . . .
C223 C -0.1424(3) 0.4617(2) 0.5225(4) 0.0840(11) Uani 1 1 d . . . . .
H22D H -0.191439 0.495104 0.471225 0.126 Uiso 1 1 calc R U . . .
H22E H -0.173211 0.468915 0.593219 0.126 Uiso 1 1 calc R U . . .
H22F H -0.162751 0.412550 0.498789 0.126 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
C101 N101 1.488(4) . ?
C101 C102 1.510(4) . ?
C101 C112 1.520(4) . ?
C102 C103 1.384(5) . ?
C102 C111 1.435(4) . ?
C103 O101 1.360(4) . ?
C103 C104 1.407(5) . ?
C104 C105 1.346(6) . ?
C105 C106 1.408(6) . ?
C106 C107 1.398(6) . ?
C106 C111 1.424(5) . ?
C107 C108 1.360(6) . ?
C108 C109 1.385(6) . ?
C109 C110 1.371(5) . ?
C110 C111 1.408(5) . ?
C112 C113 1.387(4) . ?
C112 C117 1.391(4) . ?
C113 C114 1.380(4) . ?
C114 C115 1.378(4) . ?
C115 C116 1.378(4) . ?
C115 Cl11 1.737(3) . ?
C116 C117 1.377(4) . ?
N101 C118 1.463(4) . ?
C118 C122 1.519(5) . ?
C118 C119 1.565(5) . ?
C119 C120 1.509(6) . ?
C119 C121 1.522(7) . ?
C122 O102 1.192(5) . ?
C122 O103 1.324(5) . ?
O103 C123 1.453(6) . ?
C201 N201 1.491(4) . ?
C201 C212 1.521(4) . ?
C201 C202 1.524(4) . ?
C202 C203 1.380(4) . ?
C202 C211 1.425(4) . ?
C203 O201 1.350(4) . ?
C203 C204 1.411(5) . ?
C204 C205 1.335(6) . ?
C205 C206 1.415(5) . ?
C206 C207 1.417(5) . ?
C206 C211 1.423(4) . ?
C207 C208 1.333(6) . ?
C208 C209 1.406(6) . ?
C209 C210 1.362(5) . ?
C210 C211 1.408(5) . ?
C212 C213 1.375(4) . ?
C212 C217 1.381(4) . ?
C213 C214 1.373(4) . ?
C214 C215 1.365(4) . ?
C215 C216 1.372(4) . ?
C215 Cl21 1.734(3) . ?
C216 C217 1.381(4) . ?
N201 C218 1.472(4) . ?
C218 C222 1.516(4) . ?
C218 C219 1.538(4) . ?
C219 C221 1.521(5) . ?
C219 C220 1.523(5) . ?
C222 O202 1.194(3) . ?
C222 O203 1.325(4) . ?
O203 C223 1.448(4) . ?

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
N101 C101 C102 111.2(2) . . ?
N101 C101 C112 108.3(2) . . ?
C102 C101 C112 114.0(2) . . ?
C103 C102 C111 118.6(3) . . ?
C103 C102 C101 121.3(3) . . ?
C111 C102 C101 120.0(3) . . ?
O101 C103 C102 122.3(3) . . ?
O101 C103 C104 116.4(3) . . ?
C102 C103 C104 121.3(3) . . ?
C105 C104 C103 120.2(4) . . ?
C104 C105 C106 122.0(4) . . ?
C107 C106 C105 122.2(4) . . ?
C107 C106 C111 119.3(4) . . ?
C105 C106 C111 118.5(3) . . ?
C108 C107 C106 121.4(4) . . ?
C107 C108 C109 120.1(4) . . ?
C110 C109 C108 120.1(4) . . ?
C109 C110 C111 121.7(3) . . ?
C110 C111 C106 117.3(3) . . ?
C110 C111 C102 123.3(3) . . ?
C106 C111 C102 119.5(3) . . ?
C113 C112 C117 117.6(3) . . ?
C113 C112 C101 123.2(2) . . ?
C117 C112 C101 119.2(2) . . ?
C114 C113 C112 121.7(3) . . ?
C115 C114 C113 119.1(3) . . ?
C116 C115 C114 120.7(3) . . ?
C116 C115 Cl11 119.1(2) . . ?
C114 C115 Cl11 120.2(2) . . ?
C117 C116 C115 119.3(3) . . ?
C116 C117 C112 121.6(3) . . ?
C118 N101 C101 114.5(3) . . ?
N101 C118 C122 111.4(3) . . ?
N101 C118 C119 109.8(3) . . ?
C122 C118 C119 108.8(3) . . ?
C120 C119 C121 110.8(4) . . ?
C120 C119 C118 112.1(3) . . ?
C121 C119 C118 109.6(4) . . ?
O102 C122 O103 124.3(4) . . ?
O102 C122 C118 124.1(4) . . ?
O103 C122 C118 111.6(3) . . ?
C122 O103 C123 116.5(4) . . ?
N201 C201 C212 109.5(2) . . ?
N201 C201 C202 110.4(2) . . ?
C212 C201 C202 113.9(2) . . ?
C203 C202 C211 119.2(3) . . ?
C203 C202 C201 120.2(3) . . ?
C211 C202 C201 120.6(3) . . ?
O201 C203 C202 122.9(3) . . ?
O201 C203 C204 116.5(3) . . ?
C202 C203 C204 120.5(3) . . ?
C205 C204 C203 121.2(3) . . ?
C204 C205 C206 120.8(3) . . ?
C205 C206 C207 121.3(3) . . ?
C205 C206 C211 119.1(3) . . ?
C207 C206 C211 119.6(3) . . ?
C208 C207 C206 120.9(3) . . ?
C207 C208 C209 120.2(4) . . ?
C210 C209 C208 120.8(4) . . ?
C209 C210 C211 121.0(3) . . ?
C210 C211 C206 117.5(3) . . ?
C210 C211 C202 123.4(3) . . ?
C206 C211 C202 119.0(3) . . ?
C213 C212 C217 117.8(3) . . ?
C213 C212 C201 122.7(2) . . ?
C217 C212 C201 119.5(2) . . ?
C214 C213 C212 121.5(3) . . ?
C215 C214 C213 119.4(3) . . ?
C214 C215 C216 121.0(3) . . ?
C214 C215 Cl21 119.2(3) . . ?
C216 C215 Cl21 119.8(3) . . ?
C215 C216 C217 118.6(3) . . ?
C216 C217 C212 121.6(3) . . ?
C218 N201 C201 112.8(2) . . ?
N201 C218 C222 111.9(2) . . ?
N201 C218 C219 112.7(2) . . ?
C222 C218 C219 110.2(2) . . ?
C221 C219 C220 110.9(3) . . ?
C221 C219 C218 112.7(3) . . ?
C220 C219 C218 112.5(3) . . ?
O202 C222 O203 124.3(3) . . ?
O202 C222 C218 125.1(3) . . ?
O203 C222 C218 110.5(2) . . ?
C222 O203 C223 117.1(3) . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_tc1
_database_code_depnum_ccdc_archive 'CCDC 2072227'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR Istituto di Chimica dei Composti Organometallici
Italy
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_formula_moiety         'C23 H24 F N O3'
_chemical_formula_sum            'C23 H24 F N O3'
_chemical_formula_weight         381.43

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.0522(5)
_cell_length_b                   13.5590(7)
_cell_length_c                   16.6684(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2045.86(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5181
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      43.67

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            16466
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.936
_diffrn_reflns_theta_max         28.748
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4789
_reflns_number_gt                3845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.847
_reflns_Friedel_fraction_full    0.973

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+0.1443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4789
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.4650(2) 0.90474(14) 0.77835(11) 0.0451(4) Uani 1 1 d . . . . .
H1A H 0.535777 0.862861 0.749736 0.054 Uiso 1 1 calc R U . . .
C2 C 0.3831(2) 0.96541(15) 0.71629(12) 0.0463(4) Uani 1 1 d . . . . .
C3 C 0.3247(2) 1.05683(15) 0.73419(13) 0.0521(5) Uani 1 1 d . . . . .
O1 O 0.3435(2) 1.10062(13) 0.80709(10) 0.0687(5) Uani 1 1 d . . . . .
H1O H 0.415(4) 1.063(3) 0.835(2) 0.103 Uiso 1 1 d . U . . .
C4 C 0.2427(3) 1.11058(18) 0.67717(16) 0.0634(6) Uani 1 1 d . . . . .
H4 H 0.203392 1.171667 0.690932 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2206(3) 1.07427(19) 0.60287(16) 0.0670(6) Uani 1 1 d . . . . .
H5 H 0.166299 1.110713 0.565935 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2785(2) 0.98197(18) 0.58034(13) 0.0588(6) Uani 1 1 d . . . . .
C7 C 0.2543(3) 0.9416(2) 0.50303(15) 0.0752(7) Uani 1 1 d . . . . .
H7 H 0.198942 0.977334 0.466101 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3089(4) 0.8529(2) 0.48124(15) 0.0805(8) Uani 1 1 d . . . . .
H8 H 0.291102 0.827940 0.430177 0.097 Uiso 1 1 calc R U . . .
C9 C 0.3918(4) 0.7996(2) 0.53591(14) 0.0754(7) Uani 1 1 d . . . . .
H9 H 0.431158 0.739017 0.520763 0.090 Uiso 1 1 calc R U . . .
C10 C 0.4171(3) 0.83418(17) 0.61179(13) 0.0599(6) Uani 1 1 d . . . . .
H10 H 0.472296 0.796308 0.647343 0.072 Uiso 1 1 calc R U . . .
C11 C 0.3610(2) 0.92619(15) 0.63726(12) 0.0480(5) Uani 1 1 d . . . . .
C12 C 0.3666(2) 0.83749(15) 0.82847(11) 0.0460(4) Uani 1 1 d . . . . .
C13 C 0.2206(2) 0.85735(16) 0.84490(13) 0.0562(5) Uani 1 1 d . . . . .
H13 H 0.176978 0.913365 0.823080 0.067 Uiso 1 1 calc R U . . .
C14 C 0.1375(3) 0.79580(18) 0.89311(15) 0.0663(6) Uani 1 1 d . . . . .
H14 H 0.038845 0.809840 0.903825 0.080 Uiso 1 1 calc R U . . .
C15 C 0.2028(3) 0.71446(19) 0.92447(15) 0.0657(6) Uani 1 1 d . . . . .
F1 F 0.12053(18) 0.65351(14) 0.97190(11) 0.0997(6) Uani 1 1 d . . . . .
C16 C 0.3464(3) 0.69073(19) 0.90916(17) 0.0764(8) Uani 1 1 d . . . . .
H16 H 0.388222 0.633892 0.930580 0.092 Uiso 1 1 calc R U . . .
C17 C 0.4281(3) 0.75310(18) 0.86112(15) 0.0663(6) Uani 1 1 d . . . . .
H17 H 0.526415 0.738127 0.850472 0.080 Uiso 1 1 calc R U . . .
N1 N 0.55078(18) 0.96950(14) 0.83381(10) 0.0490(4) Uani 1 1 d . . . . .
H1N H 0.582(3) 0.9295(17) 0.8762(14) 0.059 Uiso 1 1 d . U . . .
C18 C 0.6806(2) 1.01487(14) 0.79570(12) 0.0473(4) Uani 1 1 d . . . . .
H18 H 0.645547 1.054450 0.750335 0.057 Uiso 1 1 calc R U . . .
C19 C 0.7588(3) 1.08481(17) 0.85460(15) 0.0625(6) Uani 1 1 d . . . . .
H19 H 0.685527 1.134072 0.870988 0.075 Uiso 1 1 calc R U . . .
C20 C 0.8128(4) 1.0355(3) 0.93055(17) 0.0960(10) Uani 1 1 d . . . . .
H20A H 0.854820 1.084173 0.965595 0.144 Uiso 1 1 calc R U . . .
H20B H 0.886457 0.987233 0.917305 0.144 Uiso 1 1 calc R U . . .
H20C H 0.731378 1.003782 0.956945 0.144 Uiso 1 1 calc R U . . .
C21 C 0.8837(4) 1.1408(2) 0.8143(2) 0.0957(10) Uani 1 1 d . . . . .
H21A H 0.961808 1.095740 0.800976 0.144 Uiso 1 1 calc R U . . .
H21B H 0.920618 1.190334 0.850213 0.144 Uiso 1 1 calc R U . . .
H21C H 0.847717 1.171548 0.766281 0.144 Uiso 1 1 calc R U . . .
C22 C 0.7850(2) 0.93727(16) 0.76295(15) 0.0553(5) Uani 1 1 d . . . . .
O2 O 0.8209(2) 0.86460(13) 0.79815(13) 0.0835(6) Uani 1 1 d . . . . .
O3 O 0.8296(2) 0.95980(14) 0.68913(11) 0.0808(5) Uani 1 1 d . . . . .
C23 C 0.9290(4) 0.8900(3) 0.6517(3) 0.1227(14) Uani 1 1 d . . . . .
H23A H 0.878419 0.828731 0.643151 0.184 Uiso 1 1 calc R U . . .
H23B H 1.012635 0.879252 0.686089 0.184 Uiso 1 1 calc R U . . .
H23C H 0.962070 0.915852 0.601206 0.184 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
C1 N1 1.493(3) . ?
C1 C2 1.515(3) . ?
C1 C12 1.524(3) . ?
C2 C3 1.380(3) . ?
C2 C11 1.435(3) . ?
C3 O1 1.363(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.348(4) . ?
C5 C6 1.408(3) . ?
C6 C7 1.417(4) . ?
C6 C11 1.425(3) . ?
C7 C8 1.350(4) . ?
C8 C9 1.384(4) . ?
C9 C10 1.368(3) . ?
C10 C11 1.412(3) . ?
C12 C13 1.377(3) . ?
C12 C17 1.384(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.356(3) . ?
C15 C16 1.363(4) . ?
C15 F1 1.365(3) . ?
C16 C17 1.380(3) . ?
N1 C18 1.470(3) . ?
C18 C22 1.516(3) . ?
C18 C19 1.538(3) . ?
C19 C20 1.513(4) . ?
C19 C21 1.518(4) . ?
C22 O2 1.192(3) . ?
C22 O3 1.331(3) . ?
O3 C23 1.447(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.97(16) . . ?
N1 C1 C12 108.45(15) . . ?
C2 C1 C12 114.40(16) . . ?
C3 C2 C11 118.55(19) . . ?
C3 C2 C1 121.83(18) . . ?
C11 C2 C1 119.59(17) . . ?
O1 C3 C2 122.40(19) . . ?
O1 C3 C4 116.23(19) . . ?
C2 C3 C4 121.4(2) . . ?
C5 C4 C3 120.6(2) . . ?
C4 C5 C6 121.0(2) . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 C11 119.3(2) . . ?
C7 C6 C11 118.8(2) . . ?
C8 C7 C6 122.1(2) . . ?
C7 C8 C9 119.1(2) . . ?
C10 C9 C8 121.3(3) . . ?
C9 C10 C11 121.4(2) . . ?
C10 C11 C6 117.20(19) . . ?
C10 C11 C2 123.60(19) . . ?
C6 C11 C2 119.19(19) . . ?
C13 C12 C17 118.0(2) . . ?
C13 C12 C1 123.59(18) . . ?
C17 C12 C1 118.38(19) . . ?
C12 C13 C14 121.4(2) . . ?
C15 C14 C13 118.5(2) . . ?
C14 C15 C16 122.4(2) . . ?
C14 C15 F1 118.5(2) . . ?
C16 C15 F1 119.1(2) . . ?
C15 C16 C17 118.4(2) . . ?
C16 C17 C12 121.3(2) . . ?
C18 N1 C1 113.21(16) . . ?
N1 C18 C22 111.31(16) . . ?
N1 C18 C19 110.49(17) . . ?
C22 C18 C19 111.77(17) . . ?
C20 C19 C21 110.5(2) . . ?
C20 C19 C18 114.2(2) . . ?
C21 C19 C18 111.6(2) . . ?
O2 C22 O3 124.2(2) . . ?
O2 C22 C18 124.5(2) . . ?
O3 C22 C18 111.28(19) . . ?
C22 O3 C23 115.9(3) . . ?

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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_vi33
_database_code_depnum_ccdc_archive 'CCDC 2072226'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR Istituto di Chimica dei Composti Organometallici
Italy
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_formula_moiety         'C23 H25 N O3'
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.1174(7)
_cell_length_b                   13.0496(11)
_cell_length_c                   16.4573(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.831(2)
_cell_angle_gamma                90
_cell_volume                     1939.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1603
_cell_measurement_theta_min      5.27
_cell_measurement_theta_max      43.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            15332
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.999
_diffrn_reflns_theta_max         28.809
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4686
_reflns_number_gt                2562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.1622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4686
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
N1 N 0.77315(17) 0.81530(12) 0.18790(10) 0.0394(4) Uani 1 1 d . . . . .
H1N H 0.704(2) 0.8181(14) 0.2231(12) 0.050(6) Uiso 1 1 d . . . . .
O1 O 0.79789(17) 0.94823(11) 0.06750(10) 0.0591(4) Uani 1 1 d . . . . .
H1O H 0.777(3) 0.9227(19) 0.1155(15) 0.083(9) Uiso 1 1 d . . . . .
C12 C 0.81788(19) 0.68313(15) -0.00832(11) 0.0411(5) Uani 1 1 d . . . . .
O2 O 1.02822(15) 0.63066(10) 0.29052(9) 0.0565(4) Uani 1 1 d . . . . .
C13 C 0.78815(19) 0.76643(14) 0.04371(11) 0.0373(4) Uani 1 1 d . . . . .
C1 C 0.5441(2) 0.76052(13) 0.10403(11) 0.0369(4) Uani 1 1 d . . . . .
C14 C 0.8263(2) 0.86443(16) 0.02308(12) 0.0441(5) Uani 1 1 d . . . . .
C19 C 0.8990(2) 0.67984(15) 0.27614(11) 0.0430(5) Uani 1 1 d . . . . .
C18 C 0.91532(19) 0.78004(14) 0.23097(11) 0.0389(4) Uani 1 1 d . . . . .
H18 H 0.980959 0.767182 0.189619 0.047 Uiso 1 1 calc R U . . .
C2 C 0.4617(2) 0.72538(16) 0.16278(12) 0.0464(5) Uani 1 1 d . . . . .
H2 H 0.509078 0.692417 0.209176 0.056 Uiso 1 1 calc R U . . .
O3 O 0.78666(17) 0.64888(12) 0.29691(10) 0.0688(5) Uani 1 1 d . . . . .
C17 C 0.71180(19) 0.74649(14) 0.11863(11) 0.0375(4) Uani 1 1 d . . . . .
H17 H 0.732427 0.675510 0.135993 0.045 Uiso 1 1 calc R U . . .
C21 C 0.9895(2) 0.86187(16) 0.29027(13) 0.0515(5) Uani 1 1 d . . . . .
H21 H 1.078641 0.830581 0.320194 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8918(2) 0.70305(18) -0.07752(12) 0.0500(5) Uani 1 1 d . . . . .
C16 C 0.9301(2) 0.8047(2) -0.09402(13) 0.0603(6) Uani 1 1 d . . . . .
H16 H 0.978999 0.818124 -0.138914 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8975(2) 0.88305(18) -0.04633(13) 0.0561(6) Uani 1 1 d . . . . .
H15 H 0.922117 0.949708 -0.059222 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4705(2) 0.80758(16) 0.03502(12) 0.0507(5) Uani 1 1 d . . . . .
H6 H 0.523740 0.830913 -0.005660 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3183(2) 0.82036(17) 0.02578(13) 0.0566(6) Uani 1 1 d . . . . .
H5 H 0.270042 0.852736 -0.020671 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2389(2) 0.78543(17) 0.08488(14) 0.0546(6) Uani 1 1 d . . . . .
H4 H 0.136677 0.793574 0.078383 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3101(2) 0.73837(17) 0.15377(14) 0.0550(6) Uani 1 1 d . . . . .
H3 H 0.256272 0.715297 0.194287 0.066 Uiso 1 1 calc R U . . .
C7 C 0.7753(2) 0.58089(16) 0.00416(13) 0.0543(6) Uani 1 1 d . . . . .
H7 H 0.723862 0.566010 0.047798 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8076(3) 0.50334(19) -0.04620(15) 0.0731(7) Uani 1 1 d . . . . .
H8 H 0.779074 0.436613 -0.036145 0.088 Uiso 1 1 calc R U . . .
C10 C 0.9238(3) 0.6205(2) -0.12793(14) 0.0683(7) Uani 1 1 d . . . . .
H10 H 0.973736 0.633288 -0.172513 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8833(3) 0.5237(2) -0.11280(15) 0.0780(8) Uani 1 1 d . . . . .
H9 H 0.905825 0.470481 -0.146637 0.094 Uiso 1 1 calc R U . . .
C20 C 1.0302(3) 0.53490(17) 0.33510(15) 0.0719(7) Uani 1 1 d . . . . .
H20A H 0.987789 0.545101 0.384783 0.108 Uiso 1 1 calc R U . . .
H20B H 1.130454 0.511587 0.348257 0.108 Uiso 1 1 calc R U . . .
H20C H 0.973539 0.484530 0.301818 0.108 Uiso 1 1 calc R U . . .
C22 C 1.0399(3) 0.95368(18) 0.24441(16) 0.0765(8) Uani 1 1 d . . . . .
H22A H 1.101074 0.930775 0.204940 0.115 Uiso 1 1 calc R U . . .
H22B H 1.095407 0.999448 0.282609 0.115 Uiso 1 1 calc R U . . .
H22C H 0.954899 0.988802 0.216723 0.115 Uiso 1 1 calc R U . . .
C23 C 0.8921(3) 0.8938(2) 0.35363(15) 0.0848(8) Uani 1 1 d . . . . .
H23A H 0.946579 0.938801 0.392920 0.127 Uiso 1 1 calc R U . . .
H23B H 0.861922 0.834149 0.381147 0.127 Uiso 1 1 calc R U . . .
H23C H 0.806169 0.928800 0.326891 0.127 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
N1 C18 1.464(2) . ?
N1 C17 1.498(2) . ?
O1 C14 1.360(2) . ?
C12 C7 1.412(3) . ?
C12 C11 1.424(3) . ?
C12 C13 1.432(2) . ?
O2 C19 1.334(2) . ?
O2 C20 1.448(2) . ?
C13 C14 1.380(3) . ?
C13 C17 1.519(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C1 C17 1.526(2) . ?
C14 C15 1.410(3) . ?
C19 O3 1.194(2) . ?
C19 C18 1.521(3) . ?
C18 C21 1.540(3) . ?
C2 C3 1.380(3) . ?
C21 C23 1.517(3) . ?
C21 C22 1.520(3) . ?
C11 C16 1.408(3) . ?
C11 C10 1.414(3) . ?
C16 C15 1.346(3) . ?
C6 C5 1.386(3) . ?
C5 C4 1.367(3) . ?
C4 C3 1.372(3) . ?
C7 C8 1.366(3) . ?
C8 C9 1.398(3) . ?
C10 C9 1.349(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C17 113.21(14) . . ?
C7 C12 C11 117.27(19) . . ?
C7 C12 C13 123.48(17) . . ?
C11 C12 C13 119.23(18) . . ?
C19 O2 C20 117.04(16) . . ?
C14 C13 C12 118.79(17) . . ?
C14 C13 C17 121.15(17) . . ?
C12 C13 C17 120.03(16) . . ?
C2 C1 C6 118.26(18) . . ?
C2 C1 C17 118.62(16) . . ?
C6 C1 C17 123.12(17) . . ?
O1 C14 C13 122.70(17) . . ?
O1 C14 C15 116.07(19) . . ?
C13 C14 C15 121.2(2) . . ?
O3 C19 O2 123.91(19) . . ?
O3 C19 C18 125.14(18) . . ?
O2 C19 C18 110.95(16) . . ?
N1 C18 C19 111.58(15) . . ?
N1 C18 C21 111.86(15) . . ?
C19 C18 C21 110.49(15) . . ?
C3 C2 C1 121.08(19) . . ?
N1 C17 C13 110.49(14) . . ?
N1 C17 C1 108.06(14) . . ?
C13 C17 C1 114.33(14) . . ?
C23 C21 C22 111.7(2) . . ?
C23 C21 C18 112.24(18) . . ?
C22 C21 C18 111.61(17) . . ?
C16 C11 C10 121.9(2) . . ?
C16 C11 C12 118.88(19) . . ?
C10 C11 C12 119.2(2) . . ?
C15 C16 C11 121.53(19) . . ?
C16 C15 C14 120.3(2) . . ?
C1 C6 C5 120.69(19) . . ?
C4 C5 C6 120.08(19) . . ?
C5 C4 C3 120.05(19) . . ?
C4 C3 C2 119.8(2) . . ?
C8 C7 C12 121.7(2) . . ?
C7 C8 C9 120.4(2) . . ?
C9 C10 C11 121.5(2) . . ?
C10 C9 C8 119.9(2) . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_cb107
_database_code_depnum_ccdc_archive 'CCDC 2072229'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR Istituto di Chimica dei Composti Organometallici
Italy
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_formula_moiety         'C23 H24 Cl N O3'
_chemical_formula_sum            'C23 H24 Cl N O3'
_chemical_formula_weight         397.88

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.0861(7)
_cell_length_b                   9.8938(5)
_cell_length_c                   16.1156(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.9280(10)
_cell_angle_gamma                90
_cell_volume                     2078.79(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5027
_cell_measurement_theta_min      4.84
_cell_measurement_theta_max      49.86

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            16222
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         28.747
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5033
_reflns_number_gt                3514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+0.3706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5033
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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
C1 C 0.03650(11) 0.42149(14) 0.72922(9) 0.0474(3) Uani 1 1 d . . . . .
H1 H -0.029547 0.386561 0.705041 0.057 Uiso 1 1 calc R U . . .
C2 C 0.03337(12) 0.57433(14) 0.71964(9) 0.0479(3) Uani 1 1 d . . . . .
C3 C 0.12279(13) 0.64784(16) 0.72174(10) 0.0550(4) Uani 1 1 d . . . . .
C4 C 0.12157(16) 0.78947(17) 0.71501(12) 0.0678(5) Uani 1 1 d . . . . .
H4 H 0.183076 0.837039 0.718186 0.081 Uiso 1 1 calc R U . . .
C5 C 0.03170(17) 0.85705(17) 0.70394(12) 0.0706(5) Uani 1 1 d . . . . .
H5 H 0.032163 0.950823 0.699958 0.085 Uiso 1 1 calc R U . . .
C6 C -0.06224(15) 0.78807(16) 0.69838(10) 0.0589(4) Uani 1 1 d . . . . .
C7 C -0.15697(19) 0.8567(2) 0.68336(13) 0.0767(6) Uani 1 1 d . . . . .
H7 H -0.156927 0.950230 0.677348 0.092 Uiso 1 1 calc R U . . .
C8 C -0.24727(19) 0.7902(2) 0.67755(14) 0.0846(7) Uani 1 1 d . . . . .
H8 H -0.308484 0.837362 0.667072 0.101 Uiso 1 1 calc R U . . .
C9 C -0.24821(15) 0.6499(2) 0.68738(14) 0.0789(6) Uani 1 1 d . . . . .
H9 H -0.310495 0.604157 0.684082 0.095 Uiso 1 1 calc R U . . .
C10 C -0.15888(13) 0.57920(19) 0.70175(12) 0.0639(4) Uani 1 1 d . . . . .
H10 H -0.161513 0.485870 0.708124 0.077 Uiso 1 1 calc R U . . .
C11 C -0.06243(12) 0.64454(15) 0.70718(9) 0.0506(4) Uani 1 1 d . . . . .
C12 C 0.05133(11) 0.37035(15) 0.81858(10) 0.0477(3) Uani 1 1 d . . . . .
C13 C 0.08064(13) 0.45158(17) 0.88562(11) 0.0596(4) Uani 1 1 d . . . . .
H13 H 0.094237 0.542536 0.877035 0.072 Uiso 1 1 calc R U . . .
C14 C 0.09023(15) 0.3997(2) 0.96601(11) 0.0682(5) Uani 1 1 d . . . . .
H14 H 0.110754 0.455334 1.010918 0.082 Uiso 1 1 calc R U . . .
C15 C 0.06921(14) 0.2661(2) 0.97858(12) 0.0657(5) Uani 1 1 d . . . . .
C16 C 0.04071(16) 0.18296(19) 0.91347(13) 0.0714(5) Uani 1 1 d . . . . .
H16 H 0.027260 0.092096 0.922538 0.086 Uiso 1 1 calc R U . . .
C17 C 0.03201(14) 0.23514(17) 0.83379(12) 0.0623(4) Uani 1 1 d . . . . .
H17 H 0.012742 0.178299 0.789208 0.075 Uiso 1 1 calc R U . . .
C18 C 0.08372(12) 0.35841(15) 0.59054(10) 0.0518(4) Uani 1 1 d . . . . .
H18 H 0.062389 0.449588 0.572726 0.062 Uiso 1 1 calc R U . . .
C19 C 0.16827(16) 0.3130(2) 0.53647(12) 0.0711(5) Uani 1 1 d . . . . .
H19 H 0.139888 0.318384 0.478275 0.085 Uiso 1 1 calc R U . . .
C20 C 0.25966(19) 0.4072(4) 0.54603(17) 0.1252(11) Uani 1 1 d . . . . .
H20A H 0.296064 0.393812 0.599697 0.188 Uiso 1 1 calc R U . . .
H20B H 0.236450 0.499140 0.541175 0.188 Uiso 1 1 calc R U . . .
H20C H 0.304440 0.388418 0.503297 0.188 Uiso 1 1 calc R U . . .
C21 C 0.2003(3) 0.1685(3) 0.55278(18) 0.1337(13) Uani 1 1 d . . . . .
H21A H 0.251422 0.143772 0.516266 0.200 Uiso 1 1 calc R U . . .
H21B H 0.141768 0.110426 0.542880 0.200 Uiso 1 1 calc R U . . .
H21C H 0.228100 0.159344 0.609588 0.200 Uiso 1 1 calc R U . . .
C22 C -0.00851(15) 0.26632(16) 0.57574(11) 0.0605(4) Uani 1 1 d . . . . .
C23 C -0.1605(2) 0.2207(3) 0.49251(17) 0.1095(9) Uani 1 1 d . . . . .
H23A H -0.140861 0.129819 0.480454 0.164 Uiso 1 1 calc R U . . .
H23B H -0.201499 0.257174 0.445517 0.164 Uiso 1 1 calc R U . . .
H23C H -0.199453 0.220863 0.540333 0.164 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07749(6) 0.20370(7) 1.08022(4) 0.1027(2) Uani 1 1 d . . . . .
N1 N 0.11735(10) 0.36426(13) 0.67967(8) 0.0498(3) Uani 1 1 d . . . . .
H1N H 0.1320(14) 0.2841(19) 0.6968(11) 0.060 Uiso 1 1 d . U . . .
O1 O 0.21721(9) 0.58814(14) 0.73042(9) 0.0703(4) Uani 1 1 d . . . . .
H1O H 0.2029(19) 0.503(3) 0.7130(15) 0.105 Uiso 1 1 d . U . . .
O2 O -0.02613(14) 0.17184(14) 0.61885(10) 0.0948(5) Uani 1 1 d . . . . .
O3 O -0.06921(10) 0.30300(14) 0.50947(8) 0.0745(4) Uani 1 1 d . . . . .


_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
C1 N1 1.491(2) . ?
C1 C2 1.520(2) . ?
C1 C12 1.523(2) . ?
C2 C3 1.376(2) . ?
C2 C11 1.432(2) . ?
C3 O1 1.366(2) . ?
C3 C4 1.406(2) . ?
C4 C5 1.351(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.416(3) . ?
C6 C11 1.427(2) . ?
C7 C8 1.349(3) . ?
C8 C9 1.397(3) . ?
C9 C10 1.365(3) . ?
C10 C11 1.414(2) . ?
C12 C13 1.374(2) . ?
C12 C17 1.387(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.370(3) . ?
C15 C16 1.360(3) . ?
C15 Cl1 1.7449(18) . ?
C16 C17 1.380(3) . ?
C18 N1 1.467(2) . ?
C18 C22 1.515(2) . ?
C18 C19 1.533(2) . ?
C19 C21 1.506(3) . ?
C19 C20 1.514(3) . ?
C22 O2 1.199(2) . ?
C22 O3 1.326(2) . ?
C23 O3 1.452(2) . ?

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
N1 C1 C2 109.72(13) . . ?
N1 C1 C12 109.98(11) . . ?
C2 C1 C12 115.26(12) . . ?
C3 C2 C11 118.65(14) . . ?
C3 C2 C1 120.53(14) . . ?
C11 C2 C1 120.81(13) . . ?
O1 C3 C2 122.28(14) . . ?
O1 C3 C4 116.31(15) . . ?
C2 C3 C4 121.41(16) . . ?
C5 C4 C3 120.50(17) . . ?
C4 C5 C6 121.06(16) . . ?
C5 C6 C7 121.81(17) . . ?
C5 C6 C11 119.14(16) . . ?
C7 C6 C11 119.04(18) . . ?
C8 C7 C6 121.76(18) . . ?
C7 C8 C9 119.56(18) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 121.52(18) . . ?
C10 C11 C6 117.25(15) . . ?
C10 C11 C2 123.56(14) . . ?
C6 C11 C2 119.18(15) . . ?
C13 C12 C17 117.89(15) . . ?
C13 C12 C1 123.59(14) . . ?
C17 C12 C1 118.50(14) . . ?
C12 C13 C14 120.93(16) . . ?
C15 C14 C13 119.42(17) . . ?
C16 C15 C14 121.00(17) . . ?
C16 C15 Cl1 120.09(15) . . ?
C14 C15 Cl1 118.90(16) . . ?
C15 C16 C17 119.16(17) . . ?
C16 C17 C12 121.58(17) . . ?
N1 C18 C22 110.23(13) . . ?
N1 C18 C19 113.44(13) . . ?
C22 C18 C19 109.78(14) . . ?
C21 C19 C20 111.2(2) . . ?
C21 C19 C18 112.47(19) . . ?
C20 C19 C18 111.36(17) . . ?
O2 C22 O3 123.27(17) . . ?
O2 C22 C18 124.62(16) . . ?
O3 C22 C18 112.11(14) . . ?
C18 N1 C1 111.87(11) . . ?
C22 O3 C23 115.13(16) . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.034

