# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_190523sf_0m
_database_code_depnum_ccdc_archive 'CCDC 1964048'
loop_
_audit_author_name
_audit_author_address
'xiaochen Zhang' 'Nanjing Tech University'
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(E)-N-benzyl-N-(3-oxo-1,3-diphenylprop-1-en-1-yl)acetamide
_chemical_formula_moiety         'C24 H21 N O2'
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42
_chemical_melting_point          '394.36 - 395.16'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.1551(2)
_cell_length_b                   11.3650(2)
_cell_length_c                   18.1448(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.1240(10)
_cell_angle_gamma                90
_cell_volume                     1883.04(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    124(2)
_cell_measurement_theta_max      54.82
_cell_measurement_theta_min      3.385
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1207 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.7729. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21460
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.950
_diffrn_reflns_theta_min         3.996
_diffrn_ambient_temperature      124.58
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2979
_reflns_number_total             3569
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.070
_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)+(0.0404P)²+0.5245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.23682(11) 0.91156(8) 0.58260(6) 0.0377(3) Uani 1 1 d . . . . .
O2 O 0.10018(10) 0.37906(8) 0.59506(5) 0.0339(2) Uani 1 1 d . . . . .
N1 N 0.28531(11) 0.73489(9) 0.63630(6) 0.0269(3) Uani 1 1 d . . . . .
C1 C 0.20390(14) 0.80773(12) 0.58982(7) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.06997(15) 0.75764(13) 0.54840(8) 0.0356(3) Uani 1 1 d . . . . .
H2A H 0.006492 0.821993 0.529606 0.053 Uiso 1 1 calc GR . . . .
H2B H 0.016702 0.708188 0.581662 0.053 Uiso 1 1 calc GR . . . .
H2C H 0.099420 0.710090 0.506917 0.053 Uiso 1 1 calc GR . . . .
C3 C 0.24768(13) 0.61415(11) 0.64843(7) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.26923(13) 0.53685(11) 0.59490(7) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.316109 0.565753 0.553511 0.032 Uiso 1 1 calc R . . . .
C5 C 0.22754(14) 0.40974(12) 0.59311(7) 0.0264(3) Uani 1 1 d . . . . .
C6 C 0.34851(14) 0.32448(11) 0.58501(7) 0.0248(3) Uani 1 1 d . . . . .
C7 C 0.31819(15) 0.20700(11) 0.56701(7) 0.0270(3) Uani 1 1 d . . . . .
H7 H 0.219520 0.180788 0.560931 0.032 Uiso 1 1 calc R . . . .
C8 C 0.43102(15) 0.12887(12) 0.55802(7) 0.0305(3) Uani 1 1 d . . . . .
H8 H 0.409745 0.049390 0.545074 0.037 Uiso 1 1 calc R . . . .
C9 C 0.57539(16) 0.16617(12) 0.56784(7) 0.0321(3) Uani 1 1 d . . . . .
H9 H 0.652734 0.112346 0.561183 0.039 Uiso 1 1 calc R . . . .
C10 C 0.60700(15) 0.28172(13) 0.58734(8) 0.0324(3) Uani 1 1 d . . . . .
H10 H 0.705924 0.306713 0.595144 0.039 Uiso 1 1 calc R . . . .
C11 C 0.49405(14) 0.36076(12) 0.59543(7) 0.0294(3) Uani 1 1 d . . . . .
H11 H 0.515903 0.440230 0.608164 0.035 Uiso 1 1 calc R . . . .
C12 C 0.19381(13) 0.58731(11) 0.72157(7) 0.0254(3) Uani 1 1 d . . . . .
C13 C 0.11223(14) 0.67091(12) 0.75722(8) 0.0298(3) Uani 1 1 d . . . . .
H13 H 0.095543 0.746090 0.735328 0.036 Uiso 1 1 calc R . . . .
C14 C 0.05533(15) 0.64563(13) 0.82406(8) 0.0344(3) Uani 1 1 d . . . . .
H14 H -0.000810 0.703083 0.847481 0.041 Uiso 1 1 calc R . . . .
C15 C 0.08002(16) 0.53705(13) 0.85677(8) 0.0373(3) Uani 1 1 d . . . . .
H15 H 0.039568 0.519150 0.902223 0.045 Uiso 1 1 calc R . . . .
C16 C 0.16413(16) 0.45428(13) 0.82296(8) 0.0371(3) Uani 1 1 d . . . . .
H16 H 0.182258 0.379879 0.845670 0.045 Uiso 1 1 calc R . . . .
C17 C 0.22170(14) 0.47941(12) 0.75644(7) 0.0307(3) Uani 1 1 d . . . . .
H17 H 0.280851 0.422697 0.734233 0.037 Uiso 1 1 calc R . . . .
C18 C 0.41315(14) 0.78080(12) 0.68161(8) 0.0320(3) Uani 1 1 d . . . . .
H18A H 0.387320 0.789596 0.733371 0.038 Uiso 1 1 calc R . . . .
H18B H 0.438908 0.859570 0.663180 0.038 Uiso 1 1 calc R . . . .
C19 C 0.54373(14) 0.70049(12) 0.67943(7) 0.0271(3) Uani 1 1 d . . . . .
C20 C 0.59581(15) 0.63921(13) 0.74175(8) 0.0329(3) Uani 1 1 d . . . . .
H20 H 0.548122 0.647763 0.786239 0.039 Uiso 1 1 calc R . . . .
C21 C 0.71612(16) 0.56566(14) 0.74049(9) 0.0392(4) Uani 1 1 d . . . . .
H21 H 0.750873 0.524785 0.783939 0.047 Uiso 1 1 calc R . . . .
C22 C 0.78582(15) 0.55175(13) 0.67566(9) 0.0384(4) Uani 1 1 d . . . . .
H22 H 0.868766 0.501748 0.674462 0.046 Uiso 1 1 calc R . . . .
C23 C 0.73339(14) 0.61139(13) 0.61277(8) 0.0351(3) Uani 1 1 d . . . . .
H23 H 0.780005 0.601425 0.568076 0.042 Uiso 1 1 calc R . . . .
C24 C 0.61384(14) 0.68532(13) 0.61435(7) 0.0307(3) Uani 1 1 d . . . . .
H24 H 0.579195 0.726074 0.570840 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2272(16) . ?
O2 C5 1.2200(15) . ?
N1 C1 1.3644(17) . ?
N1 C3 1.4356(16) . ?
N1 C18 1.4763(17) . ?
C1 C2 1.5033(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.3348(18) . ?
C3 C12 1.4805(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.4939(18) . ?
C5 C6 1.4868(18) . ?
C6 C7 1.3976(18) . ?
C6 C11 1.3946(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3807(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3855(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3958(18) . ?
C12 C17 1.3950(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3812(19) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5069(19) . ?
C19 C20 1.3833(19) . ?
C19 C24 1.3946(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(2) . ?
C24 H24 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
C1 N1 C3 123.24(11) . . ?
C1 N1 C18 120.38(11) . . ?
C3 N1 C18 116.23(11) . . ?
O1 C1 N1 121.47(12) . . ?
O1 C1 C2 120.56(13) . . ?
N1 C1 C2 117.97(12) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C12 115.69(11) . . ?
C4 C3 N1 117.90(12) . . ?
C4 C3 C12 126.36(12) . . ?
C3 C4 H4 116.5 . . ?
C3 C4 C5 126.97(12) . . ?
C5 C4 H4 116.5 . . ?
O2 C5 C4 121.26(12) . . ?
O2 C5 C6 122.47(12) . . ?
C6 C5 C4 116.20(11) . . ?
C7 C6 C5 120.59(12) . . ?
C11 C6 C5 120.34(12) . . ?
C11 C6 C7 119.07(12) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.28(12) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.16(13) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.14(13) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.86(13) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 C6 120.46(13) . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C3 119.94(12) . . ?
C17 C12 C3 121.72(12) . . ?
C17 C12 C13 118.34(12) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.83(13) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.12(13) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.67(13) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.36(14) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.61(13) . . ?
C16 C17 H17 119.7 . . ?
N1 C18 H18A 109.3 . . ?
N1 C18 H18B 109.3 . . ?
N1 C18 C19 111.71(11) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C20 C19 C18 120.73(12) . . ?
C20 C19 C24 118.51(13) . . ?
C24 C19 C18 120.76(12) . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.23(13) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.86(14) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.36(14) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.62(13) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.41(13) . . ?
C23 C24 H24 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
####################################################################### 
# 
# 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_190726sf_0m
_database_code_depnum_ccdc_archive 'CCDC 1964135'
loop_
_audit_author_name
_audit_author_address
'xiaochen Zhang' 'Nanjing Tech University'
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 F3 N O2'
_chemical_formula_sum            'C24 H18 F3 N O2'
_chemical_formula_weight         409.39
_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 0.0148 0.0070 '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'
F F 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.3957(7)
_cell_length_b                   9.8622(5)
_cell_length_c                   14.7627(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.800(2)
_cell_angle_gamma                90
_cell_volume                     2058.78(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.38
_cell_measurement_theta_min      3.90
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1362 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.7552.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21558
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.352
_diffrn_reflns_theta_min         3.424
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3514
_reflns_number_total             3935
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.044
_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)+(0.0705P)²+0.3573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1234
_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
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F 0.18305(8) 0.69359(10) 0.44575(8) 0.0742(3) Uani 1 1 d . . . . .
F2 F 0.13197(7) 0.64701(11) 0.57012(7) 0.0692(3) Uani 1 1 d . . . . .
F3 F 0.06880(7) 0.55523(11) 0.44170(8) 0.0730(3) Uani 1 1 d . . . . .
O1 O 0.33291(9) 0.71067(10) 0.60382(8) 0.0616(3) Uani 1 1 d . . . . .
O2 O 0.19617(7) 0.37567(11) 0.45718(7) 0.0550(3) Uani 1 1 d . . . . .
N1 N 0.33992(8) 0.24874(12) 0.55365(8) 0.0470(3) Uani 1 1 d . . . . .
H1 H 0.283238 0.242833 0.519010 0.056 Uiso 1 1 calc R . . . .
C1 C 0.35952(9) 0.36361(13) 0.59873(8) 0.0367(3) Uani 1 1 d . . . . .
C2 C 0.29921(9) 0.47708(13) 0.58243(9) 0.0379(3) Uani 1 1 d . . . . .
C3 C 0.21940(9) 0.47294(14) 0.50963(9) 0.0411(3) Uani 1 1 d . . . . .
C4 C 0.15092(10) 0.59391(16) 0.49233(11) 0.0518(4) Uani 1 1 d . . . . .
C5 C 0.32363(9) 0.60187(13) 0.63970(9) 0.0402(3) Uani 1 1 d . . . . .
C6 C 0.33543(9) 0.59046(12) 0.74154(9) 0.0374(3) Uani 1 1 d . . . . .
C7 C 0.39199(11) 0.68427(16) 0.79667(11) 0.0525(4) Uani 1 1 d . . . . .
H7 H 0.420405 0.756306 0.768933 0.063 Uiso 1 1 calc R . . . .
C8 C 0.40702(14) 0.6733(2) 0.89119(13) 0.0717(5) Uani 1 1 d . . . . .
H8 H 0.446006 0.737555 0.928389 0.086 Uiso 1 1 calc R . . . .
C9 C 0.36595(15) 0.5700(2) 0.93202(12) 0.0711(5) Uani 1 1 d . . . . .
H9 H 0.377952 0.561595 0.997283 0.085 Uiso 1 1 calc R . . . .
C10 C 0.30771(13) 0.47896(17) 0.87894(12) 0.0578(4) Uani 1 1 d . . . . .
H10 H 0.277932 0.409086 0.907393 0.069 Uiso 1 1 calc R . . . .
C11 C 0.29228(10) 0.48902(14) 0.78349(10) 0.0435(3) Uani 1 1 d . . . . .
H11 H 0.251853 0.425864 0.746749 0.052 Uiso 1 1 calc R . . . .
C12 C 0.45036(8) 0.37304(12) 0.66616(8) 0.0352(3) Uani 1 1 d . . . . .
C13 C 0.46555(10) 0.29488(13) 0.74541(9) 0.0401(3) Uani 1 1 d . . . . .
H13 H 0.418983 0.231766 0.756230 0.048 Uiso 1 1 calc R . . . .
C14 C 0.54908(10) 0.30911(16) 0.80894(10) 0.0491(4) Uani 1 1 d . . . . .
H14 H 0.559256 0.256975 0.864030 0.059 Uiso 1 1 calc R . . . .
C15 C 0.61715(10) 0.39853(17) 0.79232(11) 0.0542(4) Uani 1 1 d . . . . .
H15 H 0.674369 0.407621 0.835941 0.065 Uiso 1 1 calc R . . . .
C16 C 0.60308(10) 0.47488(16) 0.71308(12) 0.0547(4) Uani 1 1 d . . . . .
H16 H 0.650788 0.535658 0.701699 0.066 Uiso 1 1 calc R . . . .
C17 C 0.51912(10) 0.46318(14) 0.64967(10) 0.0454(3) Uani 1 1 d . . . . .
H17 H 0.508851 0.516724 0.595210 0.054 Uiso 1 1 calc R . . . .
C18 C 0.40080(10) 0.12955(15) 0.55402(10) 0.0493(4) Uani 1 1 d . . . . .
H18A H 0.383420 0.059524 0.595911 0.059 Uiso 1 1 calc R . . . .
H18B H 0.467693 0.155112 0.576265 0.059 Uiso 1 1 calc R . . . .
C19 C 0.38850(9) 0.07432(14) 0.45738(9) 0.0389(3) Uani 1 1 d . . . . .
C20 C 0.41147(12) 0.15179(17) 0.38663(12) 0.0594(4) Uani 1 1 d . . . . .
H20 H 0.437567 0.239678 0.399721 0.071 Uiso 1 1 calc R . . . .
C21 C 0.39715(13) 0.1037(2) 0.29771(12) 0.0651(5) Uani 1 1 d . . . . .
H21 H 0.412425 0.158809 0.249787 0.078 Uiso 1 1 calc R . . . .
C22 C 0.36079(11) -0.02383(18) 0.27813(10) 0.0541(4) Uani 1 1 d . . . . .
H22 H 0.350953 -0.057445 0.216765 0.065 Uiso 1 1 calc R . . . .
C23 C 0.33873(10) -0.10255(15) 0.34788(10) 0.0480(3) Uani 1 1 d . . . . .
H23 H 0.314042 -0.191179 0.334629 0.058 Uiso 1 1 calc R . . . .
C24 C 0.35216(9) -0.05385(13) 0.43724(9) 0.0400(3) Uani 1 1 d . . . . .
H24 H 0.336286 -0.108898 0.484912 0.048 Uiso 1 1 calc R . . . .


_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
F1 C4 1.331(2) . ?
F2 C4 1.3360(19) . ?
F3 C4 1.3306(17) . ?
O1 C5 1.2150(17) . ?
O2 C3 1.2389(16) . ?
N1 H1 0.8800 . ?
N1 C1 1.3175(16) . ?
N1 C18 1.4656(17) . ?
C1 C2 1.4092(18) . ?
C1 C12 1.4906(16) . ?
C2 C3 1.4191(17) . ?
C2 C5 1.4971(18) . ?
C3 C4 1.5382(19) . ?
C5 C6 1.4853(19) . ?
C6 C7 1.3904(18) . ?
C6 C11 1.3836(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3838(18) . ?
C12 C17 1.3856(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3865(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.374(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5062(19) . ?
C19 C20 1.383(2) . ?
C19 C24 1.3790(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.372(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.373(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3830(19) . ?
C24 H24 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
C1 N1 H1 116.0 . . ?
C1 N1 C18 128.06(11) . . ?
C18 N1 H1 116.0 . . ?
N1 C1 C2 122.00(11) . . ?
N1 C1 C12 117.97(11) . . ?
C2 C1 C12 119.99(11) . . ?
C1 C2 C3 119.47(11) . . ?
C1 C2 C5 118.97(11) . . ?
C3 C2 C5 121.50(11) . . ?
O2 C3 C2 125.53(12) . . ?
O2 C3 C4 114.03(12) . . ?
C2 C3 C4 120.41(12) . . ?
F1 C4 F2 107.52(13) . . ?
F1 C4 C3 112.62(13) . . ?
F2 C4 C3 112.89(12) . . ?
F3 C4 F1 106.24(12) . . ?
F3 C4 F2 106.99(13) . . ?
F3 C4 C3 110.20(12) . . ?
O1 C5 C2 120.88(12) . . ?
O1 C5 C6 120.46(12) . . ?
C6 C5 C2 118.65(11) . . ?
C7 C6 C5 119.05(12) . . ?
C11 C6 C5 122.14(11) . . ?
C11 C6 C7 118.81(13) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.34(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.32(15) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.20(16) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.87(16) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 120.40(13) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C1 120.65(12) . . ?
C13 C12 C17 120.07(12) . . ?
C17 C12 C1 119.27(12) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.68(13) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.08(14) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.50(13) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.97(14) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.69(13) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
N1 C18 H18A 109.9 . . ?
N1 C18 H18B 109.9 . . ?
N1 C18 C19 108.81(11) . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 H18A 109.9 . . ?
C19 C18 H18B 109.9 . . ?
C20 C19 C18 120.87(13) . . ?
C24 C19 C18 120.55(13) . . ?
C24 C19 C20 118.57(13) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.08(15) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.03(16) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.53(14) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.54(14) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 120.23(13) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?

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
N1 H1 O2 0.88 1.92 2.6026(14) 133.0 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_191106sf_0m
_database_code_depnum_ccdc_archive 'CCDC 1964133'
loop_
_audit_author_name
_audit_author_address
'xiaochen Zhang' 'Nanjing Tech University'
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
1-(4-benzoyl-3-phenylisoquinolin-2(1H)-yl)ethan-1-one
_chemical_formula_moiety         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_chemical_melting_point          '439.96 - 441.56'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.69230(10)
_cell_length_b                   11.1552(2)
_cell_length_c                   15.2475(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.3580(10)
_cell_angle_gamma                90
_cell_volume                     1803.67(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.897
_cell_measurement_theta_min      5.008
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0871 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.8033. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19169
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.925
_diffrn_reflns_theta_min         5.006
_diffrn_ambient_temperature      170.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2933
_reflns_number_total             3407
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.039
_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)+(0.0389P)²+0.6519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.78083(11) 0.14916(9) 0.39402(7) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.87442(8) 0.73722(8) 0.44429(6) 0.0318(2) Uani 1 1 d . . . . .
N1 N 0.82151(10) 0.34761(9) 0.40711(7) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.92316(12) 0.33985(12) 0.35152(9) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.931631 0.256220 0.331362 0.032 Uiso 1 1 calc R . . . .
H1B H 1.004033 0.364097 0.385943 0.032 Uiso 1 1 calc R . . . .
C2 C 0.89326(12) 0.42122(12) 0.27289(8) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.92794(14) 0.39452(13) 0.19047(9) 0.0326(3) Uani 1 1 d . . . . .
H3 H 0.967017 0.319879 0.181278 0.039 Uiso 1 1 calc R . . . .
C4 C 0.90613(15) 0.47570(14) 0.12146(9) 0.0388(4) Uani 1 1 d . . . . .
H4 H 0.929423 0.456398 0.065074 0.047 Uiso 1 1 calc R . . . .
C5 C 0.85033(14) 0.58496(14) 0.13484(9) 0.0365(4) Uani 1 1 d . . . . .
H5 H 0.836332 0.641026 0.087710 0.044 Uiso 1 1 calc R . . . .
C6 C 0.81478(13) 0.61301(13) 0.21664(9) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.777113 0.688472 0.225406 0.035 Uiso 1 1 calc R . . . .
C7 C 0.83399(11) 0.53090(11) 0.28642(8) 0.0230(3) Uani 1 1 d . . . . .
C8 C 0.80078(11) 0.55582(11) 0.37561(8) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.79342(11) 0.46569(11) 0.43397(8) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.77432(11) 0.48165(11) 0.52793(8) 0.0222(3) Uani 1 1 d . . . . .
C11 C 0.68400(13) 0.55861(12) 0.55469(9) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.628379 0.600507 0.511674 0.034 Uiso 1 1 calc R . . . .
C12 C 0.67482(14) 0.57444(13) 0.64395(9) 0.0338(3) Uani 1 1 d . . . . .
H12 H 0.613739 0.627989 0.661757 0.041 Uiso 1 1 calc R . . . .
C13 C 0.75407(14) 0.51269(13) 0.70697(9) 0.0323(3) Uani 1 1 d . . . . .
H13 H 0.747806 0.523834 0.768022 0.039 Uiso 1 1 calc R . . . .
C14 C 0.84227(13) 0.43482(12) 0.68084(9) 0.0287(3) Uani 1 1 d . . . . .
H14 H 0.896408 0.391958 0.724181 0.034 Uiso 1 1 calc R . . . .
C15 C 0.85279(12) 0.41845(11) 0.59233(8) 0.0250(3) Uani 1 1 d . . . . .
H15 H 0.913544 0.364055 0.575133 0.030 Uiso 1 1 calc R . . . .
C16 C 0.74969(13) 0.24756(12) 0.41837(9) 0.0289(3) Uani 1 1 d . . . . .
C17 C 0.63001(15) 0.26411(15) 0.45920(11) 0.0434(4) Uani 1 1 d . . . . .
H17A H 0.568101 0.203782 0.435505 0.065 Uiso 1 1 calc GR . . . .
H17B H 0.596026 0.344423 0.445194 0.065 Uiso 1 1 calc GR . . . .
H17C H 0.647944 0.254914 0.523503 0.065 Uiso 1 1 calc GR . . . .
C18 C 0.78625(12) 0.68497(11) 0.40217(8) 0.0226(3) Uani 1 1 d . . . . .
C19 C 0.66376(11) 0.74640(11) 0.37462(8) 0.0228(3) Uani 1 1 d . . . . .
C20 C 0.56294(12) 0.68652(12) 0.32636(9) 0.0289(3) Uani 1 1 d . . . . .
H20 H 0.571705 0.604843 0.310584 0.035 Uiso 1 1 calc R . . . .
C21 C 0.45002(13) 0.74574(14) 0.30134(10) 0.0352(3) Uani 1 1 d . . . . .
H21 H 0.381910 0.705092 0.267759 0.042 Uiso 1 1 calc R . . . .
C22 C 0.43682(14) 0.86397(14) 0.32535(11) 0.0396(4) Uani 1 1 d . . . . .
H22 H 0.359325 0.904537 0.308555 0.048 Uiso 1 1 calc R . . . .
C23 C 0.53596(14) 0.92340(14) 0.37372(11) 0.0389(4) Uani 1 1 d . . . . .
H23 H 0.526067 1.004597 0.390311 0.047 Uiso 1 1 calc R . . . .
C24 C 0.64938(13) 0.86576(12) 0.39818(9) 0.0294(3) Uani 1 1 d . . . . .
H24 H 0.717424 0.907431 0.430998 0.035 Uiso 1 1 calc R . . . .


_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 C16 1.2187(17) . ?
O2 C18 1.2190(15) . ?
N1 C1 1.4640(16) . ?
N1 C9 1.4229(16) . ?
N1 C16 1.3779(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5050(18) . ?
C2 C3 1.3875(18) . ?
C2 C7 1.4052(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3854(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3989(18) . ?
C7 C8 1.4753(17) . ?
C8 C9 1.3516(17) . ?
C8 C18 1.5099(17) . ?
C9 C10 1.4836(17) . ?
C10 C11 1.3917(18) . ?
C10 C15 1.3979(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3882(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.3807(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.504(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.4901(17) . ?
C19 C20 1.3953(18) . ?
C19 C24 1.3927(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3862(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(2) . ?
C24 H24 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
C9 N1 C1 114.91(10) . . ?
C16 N1 C1 119.42(11) . . ?
C16 N1 C9 124.92(11) . . ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
N1 C1 C2 109.14(10) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
C3 C2 C1 122.54(12) . . ?
C3 C2 C7 119.85(13) . . ?
C7 C2 C1 117.52(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.61(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.85(13) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.32(14) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.42(14) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C8 117.75(11) . . ?
C6 C7 C2 118.92(12) . . ?
C6 C7 C8 123.26(12) . . ?
C7 C8 C18 118.18(11) . . ?
C9 C8 C7 120.53(11) . . ?
C9 C8 C18 121.10(11) . . ?
N1 C9 C10 116.70(10) . . ?
C8 C9 N1 117.83(11) . . ?
C8 C9 C10 124.98(11) . . ?
C11 C10 C9 122.93(11) . . ?
C11 C10 C15 118.80(12) . . ?
C15 C10 C9 118.25(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.31(13) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.30(13) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.66(12) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.70(13) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.21(12) . . ?
C14 C15 H15 119.9 . . ?
O1 C16 N1 120.88(12) . . ?
O1 C16 C17 121.11(13) . . ?
N1 C16 C17 117.99(12) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 C8 119.89(11) . . ?
O2 C18 C19 121.41(12) . . ?
C19 C18 C8 118.69(11) . . ?
C20 C19 C18 121.35(12) . . ?
C24 C19 C18 119.28(12) . . ?
C24 C19 C20 119.37(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.26(13) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.81(14) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.17(13) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.55(14) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.84(13) . . ?
C23 C24 H24 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
####################################################################### 
# 
# 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_200525sf_0m
_database_code_depnum_ccdc_archive 'CCDC 2005802'
loop_
_audit_author_name
_audit_author_address
'xiaochen Zhang' 'NANJING TECH UNIVERSITY'
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2020-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N O2'
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.9186(12)
_cell_length_b                   11.6675(10)
_cell_length_c                   13.3986(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.007(4)
_cell_angle_gamma                90
_cell_volume                     1909.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8692
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      54.849
_cell_measurement_theta_min      4.561
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.7200
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1630 before and 0.1199 after correction. The Ratio of minimum to maximum transmission is 0.7564. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17533
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.029
_diffrn_reflns_theta_min         4.560
_diffrn_ambient_temperature      185.32
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2530
_reflns_number_total             3621
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1453P)²+0.3254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2161
_refine_ls_wR_factor_ref         0.2502
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.39480(14) 0.60607(16) 0.43313(16) 0.0734(6) Uani 1 1 d . . . . .
O2 O 0.51177(15) 0.75054(17) 0.69895(15) 0.0800(6) Uani 1 1 d . . . . .
N1 N 0.33615(14) 0.74882(16) 0.59237(14) 0.0517(5) Uani 1 1 d . . . . .
C1 C 0.25205(17) 0.77770(19) 0.49491(17) 0.0501(6) Uani 1 1 d . . . . .
C2 C 0.23219(18) 0.7096(2) 0.41158(17) 0.0540(6) Uani 1 1 d . . . . .
H2 H 0.172170 0.729321 0.351048 0.065 Uiso 1 1 calc R . . . .
C3 C 0.2951(2) 0.6051(2) 0.40409(17) 0.0545(6) Uani 1 1 d . . . . .
C4 C 0.23274(19) 0.49887(19) 0.35942(17) 0.0544(6) Uani 1 1 d . . . . .
C5 C 0.2902(2) 0.3975(2) 0.3629(2) 0.0662(7) Uani 1 1 d . . . . .
H5 H 0.367815 0.397437 0.391652 0.079 Uiso 1 1 calc R . . . .
C6 C 0.2356(3) 0.2971(2) 0.3250(2) 0.0757(8) Uani 1 1 d . . . . .
H6 H 0.275906 0.228315 0.328129 0.091 Uiso 1 1 calc R . . . .
C7 C 0.1237(3) 0.2956(3) 0.2826(2) 0.0817(9) Uani 1 1 d . . . . .
H7 H 0.086412 0.225967 0.256744 0.098 Uiso 1 1 calc R . . . .
C8 C 0.0653(3) 0.3959(3) 0.2778(2) 0.0830(9) Uani 1 1 d . . . . .
H8 H -0.012182 0.395426 0.247729 0.100 Uiso 1 1 calc R . . . .
C9 C 0.1192(2) 0.4968(2) 0.3165(2) 0.0687(7) Uani 1 1 d . . . . .
H9 H 0.078485 0.565193 0.313740 0.082 Uiso 1 1 calc R . . . .
C10 C 0.1810(2) 0.8836(2) 0.4953(2) 0.0628(7) Uani 1 1 d . . . . .
C11 C 0.2322(3) 0.9606(3) 0.5910(2) 0.0889(10) Uani 1 1 d . . . . .
H11A H 0.241212 0.917076 0.655817 0.133 Uiso 1 1 calc GR . . . .
H11B H 0.184426 1.026584 0.588059 0.133 Uiso 1 1 calc GR . . . .
H11C H 0.303904 0.987414 0.590367 0.133 Uiso 1 1 calc GR . . . .
C12 C 0.1666(3) 0.9539(3) 0.3956(2) 0.0908(10) Uani 1 1 d . . . . .
H12A H 0.238461 0.978834 0.393876 0.136 Uiso 1 1 calc GR . . . .
H12B H 0.121225 1.021248 0.395532 0.136 Uiso 1 1 calc GR . . . .
H12C H 0.130887 0.906851 0.333261 0.136 Uiso 1 1 calc GR . . . .
C13 C 0.0676(2) 0.8432(3) 0.4930(4) 0.1005(12) Uani 1 1 d . . . . .
H13A H 0.038132 0.789357 0.434427 0.151 Uiso 1 1 calc GR . . . .
H13B H 0.018591 0.909310 0.483406 0.151 Uiso 1 1 calc GR . . . .
H13C H 0.073490 0.804884 0.559741 0.151 Uiso 1 1 calc GR . . . .
C14 C 0.44291(19) 0.7782(2) 0.61505(19) 0.0593(6) Uani 1 1 d . . . . .
C15 C 0.4745(2) 0.8472(3) 0.5355(2) 0.0780(8) Uani 1 1 d . . . . .
H15A H 0.515369 0.915175 0.569634 0.117 Uiso 1 1 calc GR . . . .
H15B H 0.408419 0.870930 0.478813 0.117 Uiso 1 1 calc GR . . . .
H15C H 0.520521 0.800557 0.505814 0.117 Uiso 1 1 calc GR . . . .
C16 C 0.3015(2) 0.6847(2) 0.67094(19) 0.0632(7) Uani 1 1 d . . . . .
H16A H 0.234938 0.721150 0.677694 0.076 Uiso 1 1 calc R . . . .
H16B H 0.359848 0.690358 0.740340 0.076 Uiso 1 1 calc R . . . .
C17 C 0.2780(2) 0.5603(2) 0.64406(17) 0.0580(6) Uani 1 1 d . . . . .
C18 C 0.3609(2) 0.4843(3) 0.6494(2) 0.0740(8) Uani 1 1 d . . . . .
H18 H 0.434555 0.510335 0.669538 0.089 Uiso 1 1 calc R . . . .
C19 C 0.3373(4) 0.3710(3) 0.6257(3) 0.0954(10) Uani 1 1 d . . . . .
H19 H 0.394807 0.318900 0.628719 0.114 Uiso 1 1 calc R . . . .
C20 C 0.2312(4) 0.3319(3) 0.5975(3) 0.1039(13) Uani 1 1 d . . . . .
H20 H 0.215390 0.253006 0.582258 0.125 Uiso 1 1 calc R . . . .
C21 C 0.1485(3) 0.4079(3) 0.5916(3) 0.0998(12) Uani 1 1 d . . . . .
H21 H 0.074813 0.382163 0.571354 0.120 Uiso 1 1 calc R . . . .
C22 C 0.1725(2) 0.5207(3) 0.6149(2) 0.0778(8) Uani 1 1 d . . . . .
H22 H 0.114732 0.572830 0.610753 0.093 Uiso 1 1 calc R . . . .


_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 C3 1.218(3) . ?
O2 C14 1.228(3) . ?
N1 C1 1.440(3) . ?
N1 C14 1.356(3) . ?
N1 C16 1.474(3) . ?
C1 C2 1.326(3) . ?
C1 C10 1.540(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.486(3) . ?
C3 C4 1.494(3) . ?
C4 C5 1.389(3) . ?
C4 C9 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.528(4) . ?
C10 C12 1.527(4) . ?
C10 C13 1.529(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.495(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.503(4) . ?
C17 C18 1.375(4) . ?
C17 C22 1.370(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.371(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.371(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.364(5) . ?
C22 H22 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
C1 N1 C16 116.83(18) . . ?
C14 N1 C1 123.8(2) . . ?
C14 N1 C16 119.40(19) . . ?
N1 C1 C10 117.33(19) . . ?
C2 C1 N1 120.3(2) . . ?
C2 C1 C10 122.1(2) . . ?
C1 C2 H2 117.0 . . ?
C1 C2 C3 126.0(2) . . ?
C3 C2 H2 117.0 . . ?
O1 C3 C2 121.1(2) . . ?
O1 C3 C4 120.8(2) . . ?
C2 C3 C4 118.2(2) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C9 118.6(2) . . ?
C9 C4 C3 122.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C1 112.2(2) . . ?
C11 C10 C13 110.4(3) . . ?
C12 C10 C1 109.3(2) . . ?
C12 C10 C11 108.3(2) . . ?
C12 C10 C13 107.8(3) . . ?
C13 C10 C1 108.7(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 N1 121.3(2) . . ?
O2 C14 C15 120.6(2) . . ?
N1 C14 C15 118.1(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
N1 C16 C17 113.82(19) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C17 C16 121.1(2) . . ?
C22 C17 C16 120.0(3) . . ?
C22 C17 C18 118.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.4(3) . . ?
C21 C22 H22 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_191029sf_0m
_database_code_depnum_ccdc_archive 'CCDC 1964136'
loop_
_audit_author_name
_audit_author_address
'xiaochen Zhang' 'Nanjing Tech University'
_audit_update_record             
;
2019-11-06 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O'
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.5135(6)
_cell_length_b                   11.7884(4)
_cell_length_c                   18.8103(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.090(2)
_cell_angle_gamma                90
_cell_volume                     3059.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.102
_cell_measurement_theta_min      3.909
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1909 before and 0.1078 after correction. The Ratio of minimum to maximum transmission is 0.6486. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29402
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.078
_diffrn_reflns_theta_min         3.908
_diffrn_ambient_temperature      169.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4281
_reflns_number_total             5830
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.031
_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)+(0.1371P)²+0.6294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), N1A(H1A),
  C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C14A(H14A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A),
 C21A(H21A)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O -0.08400(11) 0.34517(12) 0.37135(9) 0.0445(4) Uani 1 1 d . . . . .
N1 N 0.23393(13) 0.37862(14) 0.38683(9) 0.0350(4) Uani 1 1 d . . . . .
H1 H 0.293700 0.368639 0.386053 0.042 Uiso 1 1 calc R . . . .
C1 C 0.19656(16) 0.48058(16) 0.40301(11) 0.0332(5) Uani 1 1 d . . . . .
C2 C 0.24120(17) 0.58546(17) 0.41948(12) 0.0387(5) Uani 1 1 d . . . . .
H2 H 0.306723 0.596315 0.421220 0.046 Uiso 1 1 calc R . . . .
C3 C 0.18631(18) 0.67363(17) 0.43329(12) 0.0431(6) Uani 1 1 d . . . . .
H3 H 0.213932 0.747177 0.443869 0.052 Uiso 1 1 calc R . . . .
C4 C 0.09036(18) 0.65557(18) 0.43182(13) 0.0446(6) Uani 1 1 d . . . . .
H4 H 0.054709 0.717200 0.442661 0.053 Uiso 1 1 calc R . . . .
C5 C 0.04594(17) 0.55110(17) 0.41514(12) 0.0390(5) Uani 1 1 d . . . . .
H5 H -0.019282 0.540369 0.414254 0.047 Uiso 1 1 calc R . . . .
C6 C 0.09995(16) 0.46141(16) 0.39956(11) 0.0333(5) Uani 1 1 d . . . . .
C7 C 0.07974(15) 0.34226(16) 0.38032(11) 0.0324(5) Uani 1 1 d . . . . .
C8 C 0.16504(15) 0.29700(17) 0.37246(11) 0.0329(5) Uani 1 1 d . . . . .
C9 C 0.18819(16) 0.18177(16) 0.35166(11) 0.0338(5) Uani 1 1 d . . . . .
C10 C 0.13283(17) 0.13088(17) 0.28577(12) 0.0380(5) Uani 1 1 d . . . . .
H10 H 0.081539 0.172246 0.251957 0.046 Uiso 1 1 calc R . . . .
C11 C 0.15115(18) 0.02079(18) 0.26855(13) 0.0443(6) Uani 1 1 d . . . . .
H11 H 0.112478 -0.013309 0.223379 0.053 Uiso 1 1 calc R . . . .
C12 C 0.22625(18) -0.03937(19) 0.31759(14) 0.0463(6) Uani 1 1 d . . . . .
H12 H 0.238695 -0.115299 0.306319 0.056 Uiso 1 1 calc R . . . .
C13 C 0.28315(18) 0.01078(19) 0.38291(14) 0.0455(6) Uani 1 1 d . . . . .
H13 H 0.334884 -0.030522 0.416310 0.055 Uiso 1 1 calc R . . . .
C14 C 0.26473(17) 0.12136(17) 0.39968(13) 0.0394(5) Uani 1 1 d . . . . .
H14 H 0.304601 0.156039 0.444203 0.047 Uiso 1 1 calc R . . . .
C15 C -0.01166(16) 0.28802(17) 0.37220(11) 0.0350(5) Uani 1 1 d . . . . .
C16 C -0.02329(16) 0.16174(17) 0.36447(11) 0.0357(5) Uani 1 1 d . . . . .
C17 C -0.09437(17) 0.11704(19) 0.30337(12) 0.0423(6) Uani 1 1 d . . . . .
H17 H -0.134986 0.166222 0.266930 0.051 Uiso 1 1 calc R . . . .
C18 C -0.10597(19) 0.0008(2) 0.29562(13) 0.0490(6) Uani 1 1 d . . . . .
H18 H -0.153914 -0.029705 0.253322 0.059 Uiso 1 1 calc R . . . .
C19 C -0.0487(2) -0.07090(19) 0.34860(14) 0.0497(6) Uani 1 1 d . . . . .
H19 H -0.057015 -0.150676 0.342901 0.060 Uiso 1 1 calc R . . . .
C20 C 0.02123(19) -0.02683(18) 0.41038(13) 0.0462(6) Uani 1 1 d . . . . .
H20 H 0.060359 -0.076402 0.447353 0.055 Uiso 1 1 calc R . . . .
C21 C 0.03419(17) 0.08941(17) 0.41834(12) 0.0380(5) Uani 1 1 d . . . . .
H21 H 0.082362 0.119575 0.460623 0.046 Uiso 1 1 calc R . . . .
O1A O 0.41626(11) 0.32979(12) 0.37491(9) 0.0438(4) Uani 1 1 d . . . . .
N1A N 0.73133(13) 0.30353(14) 0.38241(9) 0.0348(4) Uani 1 1 d . . . . .
H1A H 0.790579 0.314825 0.380789 0.042 Uiso 1 1 calc R . . . .
C1A C 0.69512(16) 0.19987(17) 0.39631(11) 0.0336(5) Uani 1 1 d . . . . .
C2A C 0.74074(18) 0.09471(18) 0.40925(12) 0.0406(5) Uani 1 1 d . . . . .
H2A H 0.806320 0.085515 0.410683 0.049 Uiso 1 1 calc R . . . .
C3A C 0.68594(19) 0.00433(18) 0.41993(13) 0.0465(6) Uani 1 1 d . . . . .
H3A H 0.714053 -0.069174 0.428540 0.056 Uiso 1 1 calc R . . . .
C4A C 0.58995(19) 0.01929(18) 0.41826(13) 0.0461(6) Uani 1 1 d . . . . .
H4A H 0.554241 -0.044613 0.425864 0.055 Uiso 1 1 calc R . . . .
C5A C 0.54541(18) 0.12347(17) 0.40597(12) 0.0407(5) Uani 1 1 d . . . . .
H5A H 0.480121 0.132037 0.405445 0.049 Uiso 1 1 calc R . . . .
C6A C 0.59864(17) 0.21669(16) 0.39424(11) 0.0352(5) Uani 1 1 d . . . . .
C7A C 0.57789(15) 0.33663(16) 0.37885(11) 0.0331(5) Uani 1 1 d . . . . .
C8A C 0.66266(15) 0.38470(17) 0.37172(11) 0.0334(5) Uani 1 1 d . . . . .
C9A C 0.68627(16) 0.50221(16) 0.35548(11) 0.0329(5) Uani 1 1 d . . . . .
C10A C 0.63060(17) 0.55981(18) 0.29242(12) 0.0389(5) Uani 1 1 d . . . . .
H10A H 0.577105 0.522837 0.257811 0.047 Uiso 1 1 calc R . . . .
C11A C 0.65247(19) 0.67097(18) 0.27953(14) 0.0460(6) Uani 1 1 d . . . . .
H11A H 0.613672 0.710085 0.236464 0.055 Uiso 1 1 calc R . . . .
C12A C 0.73071(19) 0.72478(19) 0.32935(14) 0.0482(6) Uani 1 1 d . . . . .
H12A H 0.745224 0.801236 0.320929 0.058 Uiso 1 1 calc R . . . .
C13A C 0.78797(19) 0.66714(19) 0.39160(14) 0.0457(6) Uani 1 1 d . . . . .
H13A H 0.842194 0.703878 0.425547 0.055 Uiso 1 1 calc R . . . .
C14A C 0.76637(17) 0.55619(18) 0.40444(12) 0.0390(5) Uani 1 1 d . . . . .
H14A H 0.806340 0.516666 0.446846 0.047 Uiso 1 1 calc R . . . .
C15A C 0.48719(16) 0.38898(17) 0.37447(11) 0.0349(5) Uani 1 1 d . . . . .
C16A C 0.47304(16) 0.51497(17) 0.36914(11) 0.0334(5) Uani 1 1 d . . . . .
C17A C 0.40333(17) 0.56008(18) 0.30756(12) 0.0407(5) Uani 1 1 d . . . . .
H17A H 0.366541 0.511506 0.268813 0.049 Uiso 1 1 calc R . . . .
C18A C 0.38727(18) 0.67668(19) 0.30254(13) 0.0457(6) Uani 1 1 d . . . . .
H18A H 0.340931 0.708089 0.259689 0.055 Uiso 1 1 calc R . . . .
C19A C 0.43879(19) 0.74626(19) 0.35989(14) 0.0482(6) Uani 1 1 d . . . . .
H19A H 0.427646 0.825776 0.356555 0.058 Uiso 1 1 calc R . . . .
C20A C 0.50637(19) 0.70145(18) 0.42209(13) 0.0467(6) Uani 1 1 d . . . . .
H20A H 0.540236 0.749875 0.462023 0.056 Uiso 1 1 calc R . . . .
C21A C 0.52516(16) 0.58587(17) 0.42661(12) 0.0375(5) Uani 1 1 d . . . . .
H21A H 0.573358 0.555344 0.468742 0.045 Uiso 1 1 calc R . . . .


_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 C15 1.243(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.391(2) . ?
N1 C8 1.353(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(3) . ?
C6 C7 1.457(3) . ?
C7 C8 1.397(3) . ?
C7 C15 1.437(3) . ?
C8 C9 1.481(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.391(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.500(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.372(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9500 . ?
O1A C15A 1.246(2) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.387(3) . ?
N1A C8A 1.351(3) . ?
C1A C2A 1.391(3) . ?
C1A C6A 1.403(3) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.381(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.395(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.374(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.400(3) . ?
C6A C7A 1.456(3) . ?
C7A C8A 1.398(3) . ?
C7A C15A 1.433(3) . ?
C8A C9A 1.481(3) . ?
C9A C10A 1.388(3) . ?
C9A C14A 1.393(3) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.387(3) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.382(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.385(3) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(3) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.498(3) . ?
C16A C17A 1.386(3) . ?
C16A C21A 1.390(3) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.392(3) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.377(3) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.377(3) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.387(3) . ?
C21A H21A 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
C1 N1 H1 124.9 . . ?
C8 N1 H1 124.9 . . ?
C8 N1 C1 110.12(17) . . ?
N1 C1 C6 107.64(17) . . ?
C2 C1 N1 129.3(2) . . ?
C2 C1 C6 123.08(19) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C7 106.75(18) . . ?
C5 C6 C1 119.04(19) . . ?
C5 C6 C7 134.2(2) . . ?
C8 C7 C6 106.12(18) . . ?
C8 C7 C15 129.61(18) . . ?
C15 C7 C6 124.27(19) . . ?
N1 C8 C7 109.35(17) . . ?
N1 C8 C9 119.40(18) . . ?
C7 C8 C9 131.25(18) . . ?
C10 C9 C8 121.13(19) . . ?
C10 C9 C14 118.90(19) . . ?
C14 C9 C8 119.94(19) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
O1 C15 C7 120.53(18) . . ?
O1 C15 C16 117.86(19) . . ?
C7 C15 C16 121.60(19) . . ?
C17 C16 C15 119.29(19) . . ?
C21 C16 C15 121.0(2) . . ?
C21 C16 C17 119.69(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.9(2) . . ?
C20 C21 H21 120.1 . . ?
C1A N1A H1A 124.8 . . ?
C8A N1A H1A 124.8 . . ?
C8A N1A C1A 110.30(18) . . ?
N1A C1A C2A 129.1(2) . . ?
N1A C1A C6A 107.68(17) . . ?
C2A C1A C6A 123.21(19) . . ?
C1A C2A H2A 121.7 . . ?
C3A C2A C1A 116.7(2) . . ?
C3A C2A H2A 121.7 . . ?
C2A C3A H3A 119.5 . . ?
C2A C3A C4A 121.0(2) . . ?
C4A C3A H3A 119.5 . . ?
C3A C4A H4A 119.0 . . ?
C5A C4A C3A 122.1(2) . . ?
C5A C4A H4A 119.0 . . ?
C4A C5A H5A 120.8 . . ?
C4A C5A C6A 118.3(2) . . ?
C6A C5A H5A 120.8 . . ?
C1A C6A C7A 106.61(18) . . ?
C5A C6A C1A 118.67(19) . . ?
C5A C6A C7A 134.7(2) . . ?
C8A C7A C6A 106.18(18) . . ?
C8A C7A C15A 129.78(18) . . ?
C15A C7A C6A 124.02(19) . . ?
N1A C8A C7A 109.22(18) . . ?
N1A C8A C9A 119.07(18) . . ?
C7A C8A C9A 131.71(19) . . ?
C10A C9A C8A 121.55(19) . . ?
C10A C9A C14A 119.12(19) . . ?
C14A C9A C8A 119.33(19) . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A C9A 120.5(2) . . ?
C11A C10A H10A 119.8 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A C10A 120.0(2) . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C11A C12A C13A 119.9(2) . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A H13A 119.9 . . ?
C14A C13A C12A 120.1(2) . . ?
C14A C13A H13A 119.9 . . ?
C9A C14A H14A 119.9 . . ?
C13A C14A C9A 120.3(2) . . ?
C13A C14A H14A 119.9 . . ?
O1A C15A C7A 120.31(18) . . ?
O1A C15A C16A 117.34(19) . . ?
C7A C15A C16A 122.36(19) . . ?
C17A C16A C15A 119.05(19) . . ?
C17A C16A C21A 119.95(19) . . ?
C21A C16A C15A 120.92(19) . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 119.9(2) . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.1 . . ?
C19A C18A C17A 119.8(2) . . ?
C19A C18A H18A 120.1 . . ?
C18A C19A H19A 119.8 . . ?
C18A C19A C20A 120.5(2) . . ?
C20A C19A H19A 119.8 . . ?
C19A C20A H20A 119.9 . . ?
C19A C20A C21A 120.2(2) . . ?
C21A C20A H20A 119.9 . . ?
C16A C21A H21A 120.2 . . ?
C20A C21A C16A 119.6(2) . . ?
C20A C21A H21A 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
