# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_020TOR22
_database_code_depnum_ccdc_archive 'CCDC 2155771'
loop_
_audit_author_name
_audit_author_address
'Simon Hernandez-Ortega'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2022-03-01 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        5-Methyl-2,4-diphenylfuran-3-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          356-358
_chemical_formula_moiety         'C18 H13 N O'
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.7123(2)
_cell_length_b                   15.2241(4)
_cell_length_c                   18.7948(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.0860(10)
_cell_angle_gamma                90
_cell_volume                     2727.16(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      68.31

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.171
_exptl_absorpt_coefficient_mu    0.617
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            13468
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.765
_diffrn_reflns_theta_max         68.328
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4942
_reflns_number_gt                3828
_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       'APEX3 v2018.2 (Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.2 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2018 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0506P)²+1.6590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4942
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 0.88158(16) 0.67486(10) 0.45516(8) 0.0445(4) Uani 1 1 d . . . . .
C2 C 0.8846(2) 0.76516(15) 0.45726(12) 0.0424(5) Uani 1 1 d . . . . .
C3 C 0.7844(2) 0.79877(15) 0.40340(12) 0.0390(5) Uani 1 1 d . . . . .
C4 C 0.7154(2) 0.72275(15) 0.36574(12) 0.0394(5) Uani 1 1 d . . . . .
C5 C 0.7775(2) 0.64916(15) 0.39925(12) 0.0398(5) Uani 1 1 d . . . . .
C6 C 0.9964(3) 0.80360(18) 0.51365(15) 0.0566(7) Uani 1 1 d . . . . .
H6A H 0.997305 0.867560 0.507859 0.085 Uiso 1 1 calc R U . . .
H6B H 1.087567 0.779516 0.508536 0.085 Uiso 1 1 calc R U . . .
H6C H 0.978185 0.789111 0.561800 0.085 Uiso 1 1 calc R U . . .
C7 C 0.7525(2) 0.89184(15) 0.38691(12) 0.0375(5) Uani 1 1 d . . . . .
C8 C 0.7148(2) 0.92018(17) 0.31531(13) 0.0466(6) Uani 1 1 d . . . . .
H8 H 0.708483 0.878947 0.276879 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6866(3) 1.00794(17) 0.29978(14) 0.0503(6) Uani 1 1 d . . . . .
H9 H 0.659895 1.026195 0.250729 0.060 Uiso 1 1 calc R U . . .
C10 C 0.6967(2) 1.06932(17) 0.35459(14) 0.0489(6) Uani 1 1 d . . . . .
H10 H 0.678830 1.129635 0.343526 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7331(2) 1.04170(16) 0.42595(14) 0.0476(6) Uani 1 1 d . . . . .
H11 H 0.739769 1.083317 0.464121 0.057 Uiso 1 1 calc R U . . .
C12 C 0.7599(2) 0.95406(16) 0.44200(12) 0.0416(5) Uani 1 1 d . . . . .
H12 H 0.783636 0.935931 0.491205 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5990(3) 0.72423(16) 0.30640(14) 0.0488(6) Uani 1 1 d . . . . .
C14 C 0.7578(2) 0.55504(15) 0.38977(12) 0.0396(5) Uani 1 1 d . . . . .
C15 C 0.6829(3) 0.51954(17) 0.32518(13) 0.0504(6) Uani 1 1 d . . . . .
H15 H 0.643072 0.557423 0.286499 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6664(3) 0.42975(18) 0.31728(14) 0.0566(7) Uani 1 1 d . . . . .
H16 H 0.614342 0.406370 0.273387 0.068 Uiso 1 1 calc R U . . .
C17 C 0.7249(3) 0.37372(17) 0.37252(14) 0.0532(6) Uani 1 1 d . . . . .
H17 H 0.714316 0.311969 0.366565 0.064 Uiso 1 1 calc R U . . .
C18 C 0.7987(3) 0.40806(17) 0.43647(14) 0.0525(6) Uani 1 1 d . . . . .
H18 H 0.839102 0.369610 0.474620 0.063 Uiso 1 1 calc R U . . .
C19 C 0.8146(3) 0.49757(16) 0.44567(13) 0.0468(6) Uani 1 1 d . . . . .
H19 H 0.864509 0.520306 0.490323 0.056 Uiso 1 1 calc R U . . .
N20 N 0.5062(3) 0.72587(16) 0.25901(14) 0.0723(8) Uani 1 1 d . . . . .
O21 O 0.61217(16) 0.31759(11) 0.55511(8) 0.0467(4) Uani 1 1 d . . . . .
C22 C 0.6075(2) 0.22709(17) 0.55424(12) 0.0444(6) Uani 1 1 d . . . . .
C23 C 0.7093(2) 0.19289(16) 0.60618(13) 0.0439(5) Uani 1 1 d . . . . .
C24 C 0.7830(2) 0.26839(17) 0.64181(13) 0.0460(6) Uani 1 1 d . . . . .
C25 C 0.7210(2) 0.34244(17) 0.60881(12) 0.0443(6) Uani 1 1 d . . . . .
C26 C 0.4986(3) 0.19028(18) 0.49515(13) 0.0508(6) Uani 1 1 d . . . . .
H26A H 0.502452 0.125978 0.496947 0.076 Uiso 1 1 calc R U . . .
H26B H 0.515883 0.210543 0.448165 0.076 Uiso 1 1 calc R U . . .
H26C H 0.405646 0.210082 0.501437 0.076 Uiso 1 1 calc R U . . .
C27 C 0.7430(2) 0.10037(16) 0.62344(12) 0.0425(5) Uani 1 1 d . . . . .
C28 C 0.6377(2) 0.03775(16) 0.62417(12) 0.0436(5) Uani 1 1 d . . . . .
H28 H 0.542136 0.055317 0.613398 0.052 Uiso 1 1 calc R U . . .
C29 C 0.6706(3) -0.04905(17) 0.64026(13) 0.0494(6) Uani 1 1 d . . . . .
H29 H 0.597588 -0.090545 0.640497 0.059 Uiso 1 1 calc R U . . .
C30 C 0.8091(3) -0.07604(18) 0.65605(14) 0.0539(6) Uani 1 1 d . . . . .
H30 H 0.831741 -0.135870 0.666923 0.065 Uiso 1 1 calc R U . . .
C31 C 0.9140(3) -0.01493(19) 0.65580(14) 0.0571(7) Uani 1 1 d . . . . .
H31 H 1.009416 -0.032889 0.666889 0.068 Uiso 1 1 calc R U . . .
C32 C 0.8817(3) 0.07198(18) 0.63961(14) 0.0518(6) Uani 1 1 d . . . . .
H32 H 0.955344 0.113050 0.639501 0.062 Uiso 1 1 calc R U . . .
C33 C 0.8924(3) 0.26633(18) 0.70491(16) 0.0615(7) Uani 1 1 d . . . . .
C34 C 0.7447(3) 0.43629(16) 0.61765(12) 0.0448(6) Uani 1 1 d . . . . .
C35 C 0.8774(3) 0.46869(18) 0.64988(13) 0.0521(6) Uani 1 1 d . . . . .
H35 H 0.952422 0.429201 0.666554 0.063 Uiso 1 1 calc R U . . .
C36 C 0.8985(3) 0.55851(19) 0.65726(14) 0.0606(7) Uani 1 1 d . . . . .
H36 H 0.988055 0.580350 0.679593 0.073 Uiso 1 1 calc R U . . .
C37 C 0.7906(3) 0.6167(2) 0.63245(16) 0.0650(8) Uani 1 1 d . . . . .
H37 H 0.806053 0.678157 0.637474 0.078 Uiso 1 1 calc R U . . .
C38 C 0.6599(3) 0.58471(19) 0.60019(16) 0.0652(8) Uani 1 1 d . . . . .
H38 H 0.585711 0.624584 0.582989 0.078 Uiso 1 1 calc R U . . .
C39 C 0.6366(3) 0.49572(18) 0.59287(15) 0.0556(7) Uani 1 1 d . . . . .
H39 H 0.546400 0.474590 0.570836 0.067 Uiso 1 1 calc R U . . .
N40 N 0.9775(3) 0.26302(18) 0.75577(17) 0.0939(11) 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
O1 C5 1.367(3) . ?
O1 C2 1.376(3) . ?
C2 C3 1.362(3) . ?
C2 C6 1.484(3) . ?
C3 C4 1.451(3) . ?
C3 C7 1.471(3) . ?
C4 C5 1.367(3) . ?
C4 C13 1.428(3) . ?
C5 C14 1.452(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.393(3) . ?
C7 C12 1.395(3) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N20 1.139(3) . ?
C14 C19 1.397(3) . ?
C14 C15 1.399(3) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O21 C25 1.367(3) . ?
O21 C22 1.378(3) . ?
C22 C23 1.353(3) . ?
C22 C26 1.488(3) . ?
C23 C24 1.448(3) . ?
C23 C27 1.468(3) . ?
C24 C25 1.369(3) . ?
C24 C33 1.432(3) . ?
C25 C34 1.452(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.392(3) . ?
C27 C28 1.400(3) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.383(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.380(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 N40 1.138(3) . ?
C34 C39 1.396(4) . ?
C34 C35 1.404(3) . ?
C35 C36 1.386(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.382(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.386(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.376(4) . ?
C38 H38 0.9500 . ?
C39 H39 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
C5 O1 C2 108.45(17) . . ?
C3 C2 O1 110.24(19) . . ?
C3 C2 C6 134.7(2) . . ?
O1 C2 C6 115.0(2) . . ?
C2 C3 C4 105.0(2) . . ?
C2 C3 C7 127.6(2) . . ?
C4 C3 C7 127.37(19) . . ?
C5 C4 C13 125.9(2) . . ?
C5 C4 C3 107.90(19) . . ?
C13 C4 C3 126.2(2) . . ?
C4 C5 O1 108.4(2) . . ?
C4 C5 C14 135.7(2) . . ?
O1 C5 C14 115.92(19) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.2(2) . . ?
C8 C7 C3 120.5(2) . . ?
C12 C7 C3 121.3(2) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.0(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N20 C13 C4 179.6(3) . . ?
C19 C14 C15 118.4(2) . . ?
C19 C14 C5 120.1(2) . . ?
C15 C14 C5 121.5(2) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C25 O21 C22 107.71(18) . . ?
C23 C22 O21 111.0(2) . . ?
C23 C22 C26 135.2(2) . . ?
O21 C22 C26 113.7(2) . . ?
C22 C23 C24 104.8(2) . . ?
C22 C23 C27 129.0(2) . . ?
C24 C23 C27 126.2(2) . . ?
C25 C24 C33 125.8(2) . . ?
C25 C24 C23 108.0(2) . . ?
C33 C24 C23 126.0(2) . . ?
O21 C25 C24 108.5(2) . . ?
O21 C25 C34 116.1(2) . . ?
C24 C25 C34 135.4(2) . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 117.7(2) . . ?
C32 C27 C23 120.7(2) . . ?
C28 C27 C23 121.6(2) . . ?
C29 C28 C27 121.1(2) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 120.4(2) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 119.2(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C27 121.0(2) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
N40 C33 C24 178.3(3) . . ?
C39 C34 C35 119.0(2) . . ?
C39 C34 C25 120.5(2) . . ?
C35 C34 C25 120.5(2) . . ?
C36 C35 C34 119.7(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 120.7(3) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 119.6(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 120.6(3) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C34 120.4(3) . . ?
C38 C39 H39 119.8 . . ?
C34 C39 H39 119.8 . . ?

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
C5 O1 C2 C3 -0.2(3) . . . . ?
C5 O1 C2 C6 -177.7(2) . . . . ?
O1 C2 C3 C4 0.0(3) . . . . ?
C6 C2 C3 C4 176.8(3) . . . . ?
O1 C2 C3 C7 179.9(2) . . . . ?
C6 C2 C3 C7 -3.3(4) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C7 C3 C4 C5 -179.6(2) . . . . ?
C2 C3 C4 C13 177.5(2) . . . . ?
C7 C3 C4 C13 -2.4(4) . . . . ?
C13 C4 C5 O1 -177.7(2) . . . . ?
C3 C4 C5 O1 -0.4(2) . . . . ?
C13 C4 C5 C14 1.5(4) . . . . ?
C3 C4 C5 C14 178.8(2) . . . . ?
C2 O1 C5 C4 0.4(2) . . . . ?
C2 O1 C5 C14 -178.99(19) . . . . ?
C2 C3 C7 C8 142.5(2) . . . . ?
C4 C3 C7 C8 -37.6(3) . . . . ?
C2 C3 C7 C12 -37.0(3) . . . . ?
C4 C3 C7 C12 142.9(2) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C3 C7 C8 C9 -179.2(2) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C8 C7 C12 C11 -1.2(3) . . . . ?
C3 C7 C12 C11 178.4(2) . . . . ?
C4 C5 C14 C19 -162.5(3) . . . . ?
O1 C5 C14 C19 16.7(3) . . . . ?
C4 C5 C14 C15 17.8(4) . . . . ?
O1 C5 C14 C15 -163.0(2) . . . . ?
C19 C14 C15 C16 -0.2(4) . . . . ?
C5 C14 C15 C16 179.5(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C14 -1.0(4) . . . . ?
C15 C14 C19 C18 1.1(4) . . . . ?
C5 C14 C19 C18 -178.7(2) . . . . ?
C25 O21 C22 C23 0.5(3) . . . . ?
C25 O21 C22 C26 -176.58(19) . . . . ?
O21 C22 C23 C24 -0.2(3) . . . . ?
C26 C22 C23 C24 176.0(3) . . . . ?
O21 C22 C23 C27 -179.1(2) . . . . ?
C26 C22 C23 C27 -2.9(5) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C27 C23 C24 C25 178.8(2) . . . . ?
C22 C23 C24 C33 174.2(3) . . . . ?
C27 C23 C24 C33 -6.9(4) . . . . ?
C22 O21 C25 C24 -0.6(3) . . . . ?
C22 O21 C25 C34 179.1(2) . . . . ?
C33 C24 C25 O21 -173.9(2) . . . . ?
C23 C24 C25 O21 0.5(3) . . . . ?
C33 C24 C25 C34 6.5(5) . . . . ?
C23 C24 C25 C34 -179.1(3) . . . . ?
C22 C23 C27 C32 138.2(3) . . . . ?
C24 C23 C27 C32 -40.5(4) . . . . ?
C22 C23 C27 C28 -41.7(4) . . . . ?
C24 C23 C27 C28 139.6(2) . . . . ?
C32 C27 C28 C29 -0.1(3) . . . . ?
C23 C27 C28 C29 179.8(2) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C28 C29 C30 C31 0.3(4) . . . . ?
C29 C30 C31 C32 -0.4(4) . . . . ?
C30 C31 C32 C27 0.3(4) . . . . ?
C28 C27 C32 C31 0.0(4) . . . . ?
C23 C27 C32 C31 -179.9(2) . . . . ?
O21 C25 C34 C39 22.5(3) . . . . ?
C24 C25 C34 C39 -157.9(3) . . . . ?
O21 C25 C34 C35 -156.1(2) . . . . ?
C24 C25 C34 C35 23.4(4) . . . . ?
C39 C34 C35 C36 0.7(4) . . . . ?
C25 C34 C35 C36 179.4(2) . . . . ?
C34 C35 C36 C37 -0.8(4) . . . . ?
C35 C36 C37 C38 0.3(4) . . . . ?
C36 C37 C38 C39 0.2(4) . . . . ?
C37 C38 C39 C34 -0.2(4) . . . . ?
C35 C34 C39 C38 -0.2(4) . . . . ?
C25 C34 C39 C38 -178.9(2) . . . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/heptane'
_chemical_properties_physical    Moisture-sensitive,Light-sensitive
####################################################################### 
# 
# 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_114TOO22
_database_code_depnum_ccdc_archive 'CCDC 2177946'
loop_
_audit_author_name
_audit_author_address
'Diego Martinez Otero'
;CCIQS UAEM UNAM
Mexico
;
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27

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                   7.57260(10)
_cell_length_b                   12.6658(2)
_cell_length_c                   12.7853(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.7740(10)
_cell_angle_gamma                90
_cell_volume                     1224.84(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      35.59

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 83.333
_diffrn_reflns_number            25655
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         34.972
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5361
_reflns_number_gt                4572
_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       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_cell_refinement       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0624P)²+0.2569P] 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         5361
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O1 O 0.74448(8) 0.22674(5) 0.68195(5) 0.01999(12) Uani 1 1 d . . . . .
O2 O 0.52260(8) 0.11594(5) 0.63550(4) 0.01755(11) Uani 1 1 d . . . . .
N1 N 0.45028(8) 0.30371(5) 0.37112(5) 0.01235(11) Uani 1 1 d . . . . .
H1 H 0.3782(16) 0.3056(9) 0.3152(9) 0.015 Uiso 1 1 d . U . . .
C2 C 0.44620(9) 0.22976(5) 0.44758(5) 0.01195(12) Uani 1 1 d . . . . .
C3 C 0.58265(9) 0.25404(5) 0.52104(5) 0.01114(11) Uani 1 1 d . . . . .
C4 C 0.67040(9) 0.34707(5) 0.48574(5) 0.01207(12) Uani 1 1 d . . . . .
C5 C 0.58414(9) 0.37651(5) 0.39261(5) 0.01139(11) Uani 1 1 d . . . . .
C6 C 0.30840(11) 0.14535(6) 0.44285(6) 0.01905(15) Uani 1 1 d . . . . .
H6A H 0.364942 0.076326 0.453431 0.029 Uiso 1 1 calc R U . . .
H6B H 0.244961 0.146893 0.374214 0.029 Uiso 1 1 calc R U . . .
H6C H 0.224846 0.157441 0.497801 0.029 Uiso 1 1 calc R U . . .
C7 C 0.62646(9) 0.19990(6) 0.61879(5) 0.01267(12) Uani 1 1 d . . . . .
C8 C 0.82993(12) 0.39848(7) 0.53677(7) 0.02269(16) Uani 1 1 d . . . . .
H8A H 0.888436 0.441887 0.485258 0.034 Uiso 1 1 calc R U . . .
H8B H 0.911945 0.344071 0.563932 0.034 Uiso 1 1 calc R U . . .
H8C H 0.794053 0.443212 0.594570 0.034 Uiso 1 1 calc R U . . .
C9 C 0.61374(9) 0.46537(5) 0.32185(5) 0.01228(12) Uani 1 1 d . . . . .
C10 C 0.58895(10) 0.45420(6) 0.21271(6) 0.01464(13) Uani 1 1 d . . . . .
H10 H 0.550690 0.388450 0.183926 0.018 Uiso 1 1 calc R U . . .
C11 C 0.62004(10) 0.53871(6) 0.14653(6) 0.01751(14) Uani 1 1 d . . . . .
H11 H 0.602608 0.530187 0.072931 0.021 Uiso 1 1 calc R U . . .
C12 C 0.67652(11) 0.63574(6) 0.18721(7) 0.01885(14) Uani 1 1 d . . . . .
H12 H 0.698688 0.693036 0.141725 0.023 Uiso 1 1 calc R U . . .
C13 C 0.70009(11) 0.64779(6) 0.29512(7) 0.01896(14) Uani 1 1 d . . . . .
H13 H 0.738500 0.713728 0.323379 0.023 Uiso 1 1 calc R U . . .
C14 C 0.66784(10) 0.56400(6) 0.36207(6) 0.01570(13) Uani 1 1 d . . . . .
H14 H 0.682567 0.573641 0.435661 0.019 Uiso 1 1 calc R U . . .
C15 C 0.55900(11) 0.06172(7) 0.73338(6) 0.02116(15) Uani 1 1 d . . . . .
H15A H 0.481985 -0.000219 0.737033 0.032 Uiso 1 1 calc R U . . .
H15B H 0.536845 0.109439 0.791642 0.032 Uiso 1 1 calc R U . . .
H15C H 0.682891 0.039104 0.737970 0.032 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 C7 1.2233(9) . ?
O2 C7 1.3459(9) . ?
O2 C15 1.4423(9) . ?
N1 C2 1.3553(9) . ?
N1 C5 1.3879(9) . ?
N1 H1 0.879(12) . ?
C2 C3 1.3966(9) . ?
C2 C6 1.4931(10) . ?
C3 C4 1.4361(9) . ?
C3 C7 1.4499(9) . ?
C4 C5 1.3814(9) . ?
C4 C8 1.4943(10) . ?
C5 C9 1.4681(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.4044(10) . ?
C9 C10 1.4061(10) . ?
C10 C11 1.3916(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.3936(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.3910(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.3924(11) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C7 O2 C15 115.17(6) . . ?
C2 N1 C5 110.99(6) . . ?
C2 N1 H1 124.8(8) . . ?
C5 N1 H1 124.2(8) . . ?
N1 C2 C3 106.92(6) . . ?
N1 C2 C6 120.39(6) . . ?
C3 C2 C6 132.67(6) . . ?
C2 C3 C4 107.93(6) . . ?
C2 C3 C7 127.34(6) . . ?
C4 C3 C7 124.67(6) . . ?
C5 C4 C3 106.60(6) . . ?
C5 C4 C8 126.67(7) . . ?
C3 C4 C8 126.65(6) . . ?
C4 C5 N1 107.56(6) . . ?
C4 C5 C9 131.16(6) . . ?
N1 C5 C9 121.27(6) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 O2 121.91(6) . . ?
O1 C7 C3 124.54(7) . . ?
O2 C7 C3 113.54(6) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.39(6) . . ?
C14 C9 C5 120.45(6) . . ?
C10 C9 C5 121.16(6) . . ?
C11 C10 C9 120.50(7) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.62(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.29(7) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.54(7) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.64(7) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 N1 C2 C3 -0.61(8) . . . . ?
C5 N1 C2 C6 177.84(7) . . . . ?
N1 C2 C3 C4 0.17(8) . . . . ?
C6 C2 C3 C4 -178.01(8) . . . . ?
N1 C2 C3 C7 177.43(7) . . . . ?
C6 C2 C3 C7 -0.75(13) . . . . ?
C2 C3 C4 C5 0.32(8) . . . . ?
C7 C3 C4 C5 -177.04(7) . . . . ?
C2 C3 C4 C8 -176.65(8) . . . . ?
C7 C3 C4 C8 5.99(12) . . . . ?
C3 C4 C5 N1 -0.67(8) . . . . ?
C8 C4 C5 N1 176.30(7) . . . . ?
C3 C4 C5 C9 179.32(7) . . . . ?
C8 C4 C5 C9 -3.71(13) . . . . ?
C2 N1 C5 C4 0.82(8) . . . . ?
C2 N1 C5 C9 -179.17(6) . . . . ?
C15 O2 C7 O1 0.97(11) . . . . ?
C15 O2 C7 C3 -178.36(7) . . . . ?
C2 C3 C7 O1 -177.59(7) . . . . ?
C4 C3 C7 O1 -0.76(12) . . . . ?
C2 C3 C7 O2 1.73(11) . . . . ?
C4 C3 C7 O2 178.56(7) . . . . ?
C4 C5 C9 C14 -35.78(11) . . . . ?
N1 C5 C9 C14 144.21(7) . . . . ?
C4 C5 C9 C10 144.20(8) . . . . ?
N1 C5 C9 C10 -35.81(10) . . . . ?
C14 C9 C10 C11 0.93(11) . . . . ?
C5 C9 C10 C11 -179.05(7) . . . . ?
C9 C10 C11 C12 0.11(11) . . . . ?
C10 C11 C12 C13 -0.61(12) . . . . ?
C11 C12 C13 C14 0.03(12) . . . . ?
C12 C13 C14 C9 1.04(12) . . . . ?
C10 C9 C14 C13 -1.51(11) . . . . ?
C5 C9 C14 C13 178.48(7) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.879(12) 1.982(12) 2.8394(8) 164.9(11) 4_565 yes

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 'Vapour deposition'
