# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_191216e_0m
_database_code_depnum_ccdc_archive 'CCDC 2023204'
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   27.510(2)
_cell_length_b                   5.7053(5)
_cell_length_c                   10.3731(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.370(2)
_cell_angle_gamma                90
_cell_volume                     1620.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0900 before and 0.0311 after correction. The Ra'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             632
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12012
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.675
_diffrn_reflns_theta_min         1.487
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3896
_reflns_number_total             4164
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1625 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.6(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.3526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C1(H1), C2(H2), C10(H10) 
2.b Secondary CH2 refined with riding coordinates: 
 C3(H3A,H3B), C15(H15A,H15B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C17(H17) 
2.d X=CH2 refined with riding coordinates: 
 C18(H18A,H18B), C19(H19A,H19B) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1B) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59656(6) 0.9560(3) -0.00864(14) 0.0294(3) Uani 1 1 d . . . . .
H1 H 0.5660 1.0368 0.0046 0.035 Uiso 1 1 calc R . . . .
C2 C 0.58961(6) 0.6911(3) 0.01856(15) 0.0325(3) Uani 1 1 d . . . . .
H2 H 0.5717 0.6657 0.0946 0.039 Uiso 1 1 calc R . . . .
C3 C 0.56050(6) 0.6062(3) -0.10637(16) 0.0373(4) Uani 1 1 d . . . . .
H3A H 0.5656 0.4403 -0.1204 0.045 Uiso 1 1 calc R . . . .
H3B H 0.5259 0.6357 -0.1044 0.045 Uiso 1 1 calc R . . . .
C4 C 0.58161(6) 0.7521(3) -0.20851(16) 0.0343(3) Uani 1 1 d . . . . .
C5 C 0.60232(6) 0.9548(3) -0.15260(15) 0.0316(3) Uani 1 1 d . . . . .
C6 C 0.62431(7) 1.1184(3) -0.22648(18) 0.0398(4) Uani 1 1 d . . . . .
H6 H 0.6383 1.2531 -0.1886 0.048 Uiso 1 1 calc R . . . .
C7 C 0.62515(8) 1.0781(4) -0.35858(19) 0.0494(5) Uani 1 1 d . . . . .
H7 H 0.6394 1.1876 -0.4097 0.059 Uiso 1 1 calc R . . . .
C8 C 0.60490(8) 0.8760(5) -0.41413(19) 0.0522(5) Uani 1 1 d . . . . .
H8 H 0.6058 0.8508 -0.5024 0.063 Uiso 1 1 calc R . . . .
C9 C 0.58313(7) 0.7095(4) -0.33980(18) 0.0450(4) Uani 1 1 d . . . . .
H9 H 0.5699 0.5729 -0.3773 0.054 Uiso 1 1 calc R . . . .
C10 C 0.63766(6) 1.0509(3) 0.20890(15) 0.0329(3) Uani 1 1 d . . . . .
H10 H 0.6389 0.8836 0.2305 0.039 Uiso 1 1 calc R . . . .
C11 C 0.59398(6) 1.1588(3) 0.26069(15) 0.0364(4) Uani 1 1 d . . . . .
C12 C 0.58681(7) 1.3729(4) 0.30844(19) 0.0440(4) Uani 1 1 d . . . . .
H12 H 0.6093 1.4949 0.3157 0.053 Uiso 1 1 calc R . . . .
C13 C 0.53845(8) 1.3789(5) 0.3459(2) 0.0563(6) Uani 1 1 d . . . . .
H13 H 0.5233 1.5045 0.3829 0.068 Uiso 1 1 calc R . . . .
C14 C 0.51926(8) 1.1706(6) 0.3176(2) 0.0636(6) Uani 1 1 d . . . . .
H14 H 0.4876 1.1260 0.3312 0.076 Uiso 1 1 calc R . . . .
C15 C 0.68437(7) 1.1716(4) 0.27099(18) 0.0436(4) Uani 1 1 d . . . . .
H15A H 0.6830 1.3367 0.2487 0.052 Uiso 1 1 calc R . . . .
H15B H 0.6850 1.1596 0.3644 0.052 Uiso 1 1 calc R . . . .
C16 C 0.73081(8) 1.0691(5) 0.2292(2) 0.0608(6) Uani 1 1 d . . . . .
C17 C 0.74761(12) 0.8462(7) 0.2859(4) 0.0875(11) Uani 1 1 d . . . . .
H17 H 0.7738 0.7766 0.2502 0.105 Uiso 1 1 calc R . . . .
C18 C 0.73059(15) 0.7353(6) 0.3785(4) 0.0977(12) Uani 1 1 d . . . . .
H18A H 0.7044 0.7965 0.4180 0.117 Uiso 1 1 calc R . . . .
H18B H 0.7444 0.5934 0.4066 0.117 Uiso 1 1 calc R . . . .
C19 C 0.75593(11) 1.1845(10) 0.1422(3) 0.0949(12) Uani 1 1 d . . . . .
H19A H 0.7848 1.1216 0.1170 0.114 Uiso 1 1 calc R . . . .
H19B H 0.7443 1.3265 0.1077 0.114 Uiso 1 1 calc R . . . .
N1 N 0.63641(5) 1.0788(2) 0.06649(13) 0.0314(3) Uani 1 1 d . . . . .
H1A H 0.6645(8) 1.023(4) 0.045(2) 0.038 Uiso 1 1 d R . . . .
O1 O 0.63691(4) 0.5897(2) 0.03472(13) 0.0400(3) Uani 1 1 d . . . . .
H1B H 0.6345 0.4470 0.0413 0.060 Uiso 1 1 calc GR . . . .
O2 O 0.55309(6) 1.0285(3) 0.26488(16) 0.0564(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 C2 1.553(2) . ?
C1 C5 1.516(2) . ?
C1 N1 1.463(2) . ?
C2 C3 1.537(2) . ?
C2 O1 1.420(2) . ?
C3 C4 1.506(2) . ?
C4 C5 1.392(2) . ?
C4 C9 1.388(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.392(3) . ?
C7 C8 1.383(3) . ?
C8 C9 1.394(3) . ?
C10 C11 1.494(2) . ?
C10 C15 1.544(2) . ?
C10 N1 1.483(2) . ?
C11 C12 1.340(3) . ?
C11 O2 1.352(2) . ?
C12 C13 1.421(3) . ?
C13 C14 1.322(4) . ?
C14 O2 1.385(3) . ?
C15 C16 1.505(3) . ?
C16 C17 1.458(5) . ?
C16 C19 1.358(5) . ?
C17 C18 1.276(6) . ?

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
C5 C1 C2 101.57(12) . . ?
N1 C1 C2 117.93(13) . . ?
N1 C1 C5 112.61(13) . . ?
C3 C2 C1 102.52(13) . . ?
O1 C2 C1 106.92(13) . . ?
O1 C2 C3 111.76(14) . . ?
C4 C3 C2 102.38(13) . . ?
C5 C4 C3 109.63(14) . . ?
C9 C4 C3 129.99(17) . . ?
C9 C4 C5 120.38(17) . . ?
C4 C5 C1 109.74(13) . . ?
C6 C5 C1 129.37(15) . . ?
C6 C5 C4 120.89(15) . . ?
C5 C6 C7 118.85(17) . . ?
C8 C7 C6 120.34(19) . . ?
C7 C8 C9 121.00(18) . . ?
C4 C9 C8 118.53(19) . . ?
C11 C10 C15 109.39(14) . . ?
N1 C10 C11 111.67(13) . . ?
N1 C10 C15 107.96(13) . . ?
C12 C11 C10 131.28(17) . . ?
C12 C11 O2 109.74(16) . . ?
O2 C11 C10 118.98(16) . . ?
C11 C12 C13 107.3(2) . . ?
C14 C13 C12 106.4(2) . . ?
C13 C14 O2 110.18(19) . . ?
C16 C15 C10 113.72(16) . . ?
C17 C16 C15 118.0(3) . . ?
C19 C16 C15 120.1(3) . . ?
C19 C16 C17 122.0(3) . . ?
C18 C17 C16 127.7(3) . . ?
C1 N1 C10 115.18(12) . . ?
C11 O2 C14 106.40(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1B N1 0.82 2.12 2.9331(18) 173.7 1_545

_olex2_submission_special_instructions 'No special instructions were received'
