# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_mo_201124b_0m
_database_code_depnum_ccdc_archive 'CCDC 2081904'
loop_
_audit_author_name
_audit_author_address
Ac-H
;Wuhan University
China
;
_audit_update_record             
;
2021-05-05 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C-TPA
_chemical_name_systematic        9,9-dimethyl-10-phenyl-9,10-dihydroacridine
_chemical_formula_moiety         'C21 H19 N'
_chemical_formula_sum            'C21 H19 N'
_chemical_formula_weight         285.37
_chemical_melting_point          114
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'

_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                   11.566(3)
_cell_length_b                   8.165(2)
_cell_length_c                   17.398(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.917(5)
_cell_angle_gamma                90
_cell_volume                     1607.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4713
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1615 before and 0.0672 after correction. The Ratio of minimum to maximum transmission is 0.6324. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10847
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.457
_diffrn_reflns_theta_min         1.944
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2240
_reflns_number_total             2927
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0813P)²+0.2615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.037
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.18755(18) 0.4048(3) 0.20157(12) 0.0682(6) Uani 1 1 d . . . . .
H1 H 1.2453 0.4848 0.2156 0.082 Uiso 1 1 calc R . . . .
C2 C 1.21276(16) 0.2655(3) 0.16478(11) 0.0636(5) Uani 1 1 d . . . . .
H2 H 1.2875 0.2514 0.1538 0.076 Uiso 1 1 calc R . . . .
C3 C 1.12785(14) 0.1451(2) 0.14379(10) 0.0497(4) Uani 1 1 d . . . . .
H3 H 1.1449 0.0506 0.1185 0.060 Uiso 1 1 calc R . . . .
C4 C 1.01780(13) 0.1669(2) 0.16085(9) 0.0421(4) Uani 1 1 d . . . . .
C5 C 0.99211(17) 0.3077(2) 0.19806(11) 0.0558(5) Uani 1 1 d . . . . .
H5 H 0.9178(18) 0.318(2) 0.2109(11) 0.058(5) Uiso 1 1 d . . . . .
C6 C 1.07691(19) 0.4279(3) 0.21816(12) 0.0664(5) Uani 1 1 d . . . . .
H6 H 1.0565(19) 0.531(3) 0.2440(13) 0.081(6) Uiso 1 1 d . . . . .
C7 C 0.84072(12) 0.06028(19) 0.07218(9) 0.0395(4) Uani 1 1 d . . . . .
C8 C 0.83042(16) 0.2032(2) 0.02871(10) 0.0515(4) Uani 1 1 d . . . . .
H8 H 0.8867 0.2854 0.0420 0.062 Uiso 1 1 calc R . . . .
C9 C 0.73690(19) 0.2250(3) -0.03442(11) 0.0649(5) Uani 1 1 d . . . . .
H9 H 0.7312 0.3207 -0.0639 0.078 Uiso 1 1 calc R . . . .
C10 C 0.65248(18) 0.1052(3) -0.05348(12) 0.0678(6) Uani 1 1 d . . . . .
H10 H 0.5873 0.1220 -0.0940 0.081 Uiso 1 1 calc R . . . .
C11 C 0.66484(16) -0.0392(3) -0.01239(11) 0.0592(5) Uani 1 1 d . . . . .
H11 H 0.601(2) -0.126(3) -0.0265(12) 0.076(6) Uiso 1 1 d . . . . .
C12 C 0.76059(13) -0.0676(2) 0.04963(9) 0.0448(4) Uani 1 1 d . . . . .
C13 C 0.91403(13) -0.07277(19) 0.19774(9) 0.0419(4) Uani 1 1 d . . . . .
C14 C 0.97341(14) -0.0551(2) 0.27541(10) 0.0527(4) Uani 1 1 d . . . . .
H14 H 1.0272 0.0298 0.2894 0.063 Uiso 1 1 calc R . . . .
C15 C 0.95217(18) -0.1644(3) 0.33202(11) 0.0646(6) Uani 1 1 d . . . . .
H15 H 0.9929 -0.1535 0.3838 0.078 Uiso 1 1 calc R . . . .
C16 C 0.87138(19) -0.2887(3) 0.31208(13) 0.0699(6) Uani 1 1 d . . . . .
H16 H 0.8553 -0.3596 0.3504 0.084 Uiso 1 1 calc R . . . .
C17 C 0.81484(17) -0.3070(2) 0.23530(12) 0.0633(5) Uani 1 1 d . . . . .
H17 H 0.7608 -0.3920 0.2222 0.076 Uiso 1 1 calc R . . . .
C18 C 0.83548(14) -0.2030(2) 0.17627(10) 0.0485(4) Uani 1 1 d . . . . .
C19 C 0.78767(16) -0.2332(2) 0.08944(11) 0.0546(5) Uani 1 1 d . . . . .
C20 C 0.6811(2) -0.3489(3) 0.07395(16) 0.0923(8) Uani 1 1 d . . . . .
H20A H 0.6171 -0.3003 0.0933 0.138 Uiso 1 1 calc GR . . . .
H20B H 0.7025 -0.4511 0.1004 0.138 Uiso 1 1 calc GR . . . .
H20C H 0.6569 -0.3679 0.0185 0.138 Uiso 1 1 calc GR . . . .
C21 C 0.8890(2) -0.3132(2) 0.05586(12) 0.0677(6) Uani 1 1 d . . . . .
H21A H 0.8614 -0.3364 0.0010 0.102 Uiso 1 1 calc GR . . . .
H21B H 0.9133 -0.4132 0.0835 0.102 Uiso 1 1 calc GR . . . .
H21C H 0.9549 -0.2393 0.0623 0.102 Uiso 1 1 calc GR . . . .
N1 N 0.93109(10) 0.04008(16) 0.13987(7) 0.0418(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.366(3) . ?
C1 C6 1.382(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(2) . ?
C4 C5 1.381(2) . ?
C4 N1 1.435(2) . ?
C5 H5 0.94(2) . ?
C5 C6 1.380(3) . ?
C6 H6 1.01(2) . ?
C7 C8 1.383(2) . ?
C7 C12 1.397(2) . ?
C7 N1 1.4136(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C11 H11 1.02(2) . ?
C11 C12 1.397(2) . ?
C12 C19 1.522(3) . ?
C13 C14 1.391(2) . ?
C13 C18 1.398(2) . ?
C13 N1 1.408(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(2) . ?
C18 C19 1.518(3) . ?
C19 C20 1.532(3) . ?
C19 C21 1.557(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.51(18) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.43(18) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.24(17) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.43(16) . . ?
C3 C4 N1 118.71(15) . . ?
C5 C4 N1 120.86(15) . . ?
C4 C5 H5 118.8(11) . . ?
C6 C5 C4 120.00(18) . . ?
C6 C5 H5 121.2(11) . . ?
C1 C6 H6 121.3(13) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 119.3(13) . . ?
C8 C7 C12 119.99(14) . . ?
C8 C7 N1 121.30(14) . . ?
C12 C7 N1 118.71(14) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.47(17) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.02(18) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.61(17) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 118.9(12) . . ?
C10 C11 C12 121.75(18) . . ?
C12 C11 H11 119.3(12) . . ?
C7 C12 C19 118.28(14) . . ?
C11 C12 C7 117.85(16) . . ?
C11 C12 C19 123.69(16) . . ?
C14 C13 C18 120.09(15) . . ?
C14 C13 N1 120.84(15) . . ?
C18 C13 N1 119.06(14) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.89(18) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.41(19) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.35(18) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.23(19) . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C19 118.19(14) . . ?
C17 C18 C13 117.93(17) . . ?
C17 C18 C19 123.55(17) . . ?
C12 C19 C20 112.68(17) . . ?
C12 C19 C21 107.59(14) . . ?
C18 C19 C12 107.87(14) . . ?
C18 C19 C20 112.94(16) . . ?
C18 C19 C21 107.09(15) . . ?
C20 C19 C21 108.41(17) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C4 119.04(12) . . ?
C13 N1 C4 118.94(12) . . ?
C13 N1 C7 118.90(12) . . ?

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
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 N1 -179.05(15) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 N1 C7 -102.03(17) . . . . ?
C3 C4 N1 C13 98.19(17) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C5 C4 N1 C7 78.54(19) . . . . ?
C5 C4 N1 C13 -81.25(19) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C7 C12 C19 C18 41.22(19) . . . . ?
C7 C12 C19 C20 166.56(17) . . . . ?
C7 C12 C19 C21 -74.00(19) . . . . ?
C8 C7 C12 C11 -6.3(2) . . . . ?
C8 C7 C12 C19 168.92(15) . . . . ?
C8 C7 N1 C4 -3.8(2) . . . . ?
C8 C7 N1 C13 156.00(15) . . . . ?
C8 C9 C10 C11 -3.5(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C7 3.9(3) . . . . ?
C10 C11 C12 C19 -171.06(17) . . . . ?
C11 C12 C19 C18 -143.85(16) . . . . ?
C11 C12 C19 C20 -18.5(3) . . . . ?
C11 C12 C19 C21 100.9(2) . . . . ?
C12 C7 C8 C9 4.0(3) . . . . ?
C12 C7 N1 C4 176.44(13) . . . . ?
C12 C7 N1 C13 -23.8(2) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C13 C18 C19 C12 -40.51(19) . . . . ?
C13 C18 C19 C20 -165.70(17) . . . . ?
C13 C18 C19 C21 75.03(18) . . . . ?
C14 C13 C18 C17 3.3(2) . . . . ?
C14 C13 C18 C19 -170.49(15) . . . . ?
C14 C13 N1 C4 4.8(2) . . . . ?
C14 C13 N1 C7 -154.99(14) . . . . ?
C14 C15 C16 C17 2.2(3) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 C13 -2.1(3) . . . . ?
C16 C17 C18 C19 171.25(17) . . . . ?
C17 C18 C19 C12 146.11(16) . . . . ?
C17 C18 C19 C20 20.9(3) . . . . ?
C17 C18 C19 C21 -98.34(19) . . . . ?
C18 C13 C14 C15 -1.7(2) . . . . ?
C18 C13 N1 C4 -175.69(13) . . . . ?
C18 C13 N1 C7 24.5(2) . . . . ?
N1 C4 C5 C6 179.64(17) . . . . ?
N1 C7 C8 C9 -175.80(16) . . . . ?
N1 C7 C12 C11 173.47(14) . . . . ?
N1 C7 C12 C19 -11.3(2) . . . . ?
N1 C13 C14 C15 177.74(14) . . . . ?
N1 C13 C18 C17 -176.23(14) . . . . ?
N1 C13 C18 C19 10.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 2081906'
loop_
_audit_author_name
_audit_author_address
Ac-OMe
;Wuhan University
China
;
_audit_update_record             
;
2021-05-05 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C-TPA-OMe
_chemical_name_systematic        
10-(4-methoxyphenyl)-9,9-dimethyl-9,10-dihydroacridine
_chemical_formula_moiety         'C22 H21 N O'
_chemical_formula_sum            'C22 H21 N O'
_chemical_formula_weight         315.40
_chemical_melting_point          152
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.852(9)
_cell_length_b                   8.143(6)
_cell_length_c                   17.994(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.816(12)
_cell_angle_gamma                90
_cell_volume                     1724(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5128
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.89
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1336 before and 0.0555 after correction. The Ratio of minimum to maximum transmission is 0.8533. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17517
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.845
_diffrn_reflns_theta_min         1.956
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3653
_reflns_number_total             5515
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+0.4140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3), C15(H15), C16(H16), C17(H17), C18(H18), C10(H10),
 C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.033
;
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
C22 C 0.9683(2) 0.8439(3) 0.22844(16) 0.1003(9) Uani 1 1 d . . . . .
H22A H 1.0470 0.8678 0.2258 0.150 Uiso 1 1 calc GR . . . .
H22B H 0.9601 0.7917 0.2753 0.150 Uiso 1 1 calc GR . . . .
H22C H 0.9254 0.9442 0.2246 0.150 Uiso 1 1 calc GR . . . .
C7 C 0.73237(14) 0.2026(2) -0.08048(8) 0.0499(4) Uani 1 1 d . . . . .
H7 H 0.7326 0.2086 -0.1321 0.060 Uiso 1 1 calc R . . . .
O1 O 0.64918(12) -0.05696(16) -0.09776(7) 0.0645(3) Uani 1 1 d . . . . .
C4 C 0.73011(13) 0.1855(2) 0.07236(8) 0.0469(3) Uani 1 1 d . . . . .
H4 H 0.7291 0.1802 0.1239 0.056 Uiso 1 1 calc R . . . .
C3 C 0.68569(13) 0.0570(2) 0.02794(8) 0.0486(3) Uani 1 1 d . . . . .
H3 H 0.6546 -0.0339 0.0493 0.058 Uiso 1 1 calc R . . . .
C21 C 0.94268(16) 0.8151(2) 0.08926(12) 0.0640(5) Uani 1 1 d . . . . .
H21A H 0.8978 0.9134 0.0835 0.096 Uiso 1 1 calc GR . . . .
H21B H 0.9201 0.7420 0.0483 0.096 Uiso 1 1 calc GR . . . .
H21C H 1.0215 0.8425 0.0897 0.096 Uiso 1 1 calc GR . . . .
C20 C 0.92425(14) 0.7298(2) 0.16434(9) 0.0509(4) Uani 1 1 d . . . . .
N1 N 0.82465(9) 0.45449(14) 0.08738(7) 0.0403(3) Uani 1 1 d . . . . .
C6 C 0.77637(13) 0.3311(2) -0.03570(8) 0.0455(3) Uani 1 1 d . . . . .
C2 C 0.68803(12) 0.06504(19) -0.04901(8) 0.0452(3) Uani 1 1 d . . . . .
C9 C 0.98626(12) 0.56603(18) 0.16643(7) 0.0412(3) Uani 1 1 d . . . . .
C8 C 0.93738(11) 0.43729(17) 0.12242(7) 0.0376(3) Uani 1 1 d . . . . .
C5 C 0.77612(11) 0.32229(18) 0.04121(7) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.6170(2) -0.2083(3) -0.06677(13) 0.0784(6) Uani 1 1 d . . . . .
H1A H 0.6796 -0.2512 -0.0338 0.118 Uiso 1 1 calc GR . . . .
H1B H 0.5961 -0.2854 -0.1064 0.118 Uiso 1 1 calc GR . . . .
H1C H 0.5534 -0.1903 -0.0393 0.118 Uiso 1 1 calc GR . . . .
C19 C 0.79729(13) 0.69533(19) 0.16224(8) 0.0455(3) Uani 1 1 d . . . . .
C14 C 0.75095(11) 0.56543(17) 0.11768(7) 0.0403(3) Uani 1 1 d . . . . .
C15 C 0.63259(13) 0.5477(2) 0.10336(10) 0.0541(4) Uani 1 1 d . . . . .
H15 H 0.6018 0.4640 0.0721 0.065 Uiso 1 1 calc R . . . .
C16 C 0.56130(16) 0.6546(3) 0.13558(12) 0.0679(5) Uani 1 1 d . . . . .
H16 H 0.4829 0.6437 0.1250 0.081 Uiso 1 1 calc R . . . .
C17 C 0.60581(18) 0.7765(3) 0.18311(12) 0.0717(6) Uani 1 1 d . . . . .
H17 H 0.5579 0.8449 0.2064 0.086 Uiso 1 1 calc R . . . .
C18 C 0.72219(17) 0.7968(2) 0.19598(10) 0.0615(5) Uani 1 1 d . . . . .
H18 H 0.7517 0.8801 0.2279 0.074 Uiso 1 1 calc R . . . .
C10 C 1.09427(14) 0.5413(2) 0.20478(9) 0.0525(4) Uani 1 1 d . . . . .
H10 H 1.1267 0.6236 0.2362 0.063 Uiso 1 1 calc R . . . .
C11 C 1.15426(14) 0.3984(3) 0.19752(10) 0.0598(5) Uani 1 1 d . . . . .
H11 H 1.2259 0.3847 0.2240 0.072 Uiso 1 1 calc R . . . .
C12 C 1.10788(14) 0.2764(2) 0.15104(11) 0.0582(4) Uani 1 1 d . . . . .
H12 H 1.1494 0.1816 0.1445 0.070 Uiso 1 1 calc R . . . .
C13 C 0.99925(13) 0.29400(19) 0.11387(9) 0.0487(3) Uani 1 1 d . . . . .
H13 H 0.9675 0.2101 0.0831 0.058 Uiso 1 1 calc R . . . .
H6 H 0.8091(15) 0.427(2) -0.0580(10) 0.053(5) Uiso 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
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C20 1.524(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.384(2) . ?
C7 C2 1.386(2) . ?
O1 C2 1.368(2) . ?
O1 C1 1.423(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(2) . ?
C4 C5 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.390(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 C20 1.558(3) . ?
C20 C9 1.521(2) . ?
C20 C19 1.527(3) . ?
N1 C8 1.4150(19) . ?
N1 C5 1.4375(19) . ?
N1 C14 1.4105(18) . ?
C6 C5 1.386(2) . ?
C6 H6 0.982(18) . ?
C9 C8 1.397(2) . ?
C9 C10 1.395(2) . ?
C8 C13 1.396(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C19 C14 1.400(2) . ?
C19 C18 1.404(2) . ?
C14 C15 1.403(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9300 . ?

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
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C2 120.52(14) . . ?
C2 C7 H7 119.7 . . ?
C2 O1 C1 117.58(15) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.01(14) . . ?
C5 C4 H4 119.5 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.27(14) . . ?
C2 C3 H3 120.4 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
C22 C20 C21 108.28(19) . . ?
C22 C20 C19 112.25(15) . . ?
C9 C20 C22 113.26(16) . . ?
C9 C20 C21 107.18(13) . . ?
C9 C20 C19 108.16(13) . . ?
C19 C20 C21 107.44(13) . . ?
C8 N1 C5 118.38(11) . . ?
C14 N1 C8 119.11(12) . . ?
C14 N1 C5 118.64(12) . . ?
C7 C6 C5 119.79(15) . . ?
C7 C6 H6 120.4(10) . . ?
C5 C6 H6 119.8(10) . . ?
C7 C2 C3 119.90(14) . . ?
O1 C2 C7 116.09(14) . . ?
O1 C2 C3 124.01(15) . . ?
C8 C9 C20 118.49(13) . . ?
C10 C9 C20 123.46(14) . . ?
C10 C9 C8 117.80(14) . . ?
C9 C8 N1 118.97(12) . . ?
C13 C8 N1 120.93(13) . . ?
C13 C8 C9 120.10(14) . . ?
C4 C5 N1 121.15(13) . . ?
C6 C5 C4 119.49(14) . . ?
C6 C5 N1 119.35(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C19 C20 118.14(12) . . ?
C14 C19 C18 117.82(16) . . ?
C18 C19 C20 123.68(16) . . ?
C19 C14 N1 119.12(13) . . ?
C19 C14 C15 119.90(13) . . ?
C15 C14 N1 120.98(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.28(18) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.37(18) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.52(15) . . ?
C18 C17 H17 120.2 . . ?
C19 C18 H18 119.0 . . ?
C17 C18 C19 121.92(19) . . ?
C17 C18 H18 119.0 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.92(16) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.72(15) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.10(16) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.22(16) . . ?
C12 C13 H13 119.9 . . ?

_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_y_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2081905'
loop_
_audit_author_name
_audit_author_address
Ac-Me
;Wuhan University
China
;
_audit_update_record             
;
2021-05-05 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C-TPA-Me
_chemical_name_systematic        
9,9-dimethyl-10-(p-tolyl)-9,10-dihydroacridine
_chemical_formula_moiety         'C22 H21 N'
_chemical_formula_sum            'C22 H21 N'
_chemical_formula_weight         299.40
_chemical_melting_point          150
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'

_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                   9.385(2)
_cell_length_b                   22.876(6)
_cell_length_c                   8.232(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.446(3)
_cell_angle_gamma                90
_cell_volume                     1703.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.54
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.3476
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11608
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.780
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2794
_reflns_number_total             3321
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0814P)²+1.8668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2090
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C6(H6), C9(H9), C11(H11), C7(H7), C4(H4), C10(H10), C16(H16), C18(H18), 
 C19(H19), C12(H12), C17(H17), C3(H3) 
2.b Idealised Me refined as rotating group: 
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.033 
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1245(2) 0.38174(9) 0.1220(3) 0.0309(5) Uani 1 1 d . . . . .
C5 C 0.1946(2) 0.41158(10) 0.0092(3) 0.0294(5) Uani 1 1 d . . . . .
C15 C -0.0981(3) 0.34210(10) 0.1777(3) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.2134(3) 0.35116(10) 0.2605(3) 0.0287(5) Uani 1 1 d . . . . .
C20 C -0.0268(3) 0.36708(10) 0.0641(3) 0.0295(5) Uani 1 1 d . . . . .
C13 C 0.1457(3) 0.32451(10) 0.3758(3) 0.0294(5) Uani 1 1 d . . . . .
C6 C 0.2511(3) 0.38109(11) -0.1051(3) 0.0373(6) Uani 1 1 d . . . . .
H6 H 0.2436 0.3406 -0.1111 0.045 Uiso 1 1 calc R . . . .
C14 C -0.0147(3) 0.33996(11) 0.3635(3) 0.0344(6) Uani 1 1 d . . . . .
C9 C 0.3663(3) 0.34677(12) 0.2859(3) 0.0369(6) Uani 1 1 d . . . . .
H9 H 0.4122 0.3663 0.2147 0.044 Uiso 1 1 calc R . . . .
C11 C 0.3830(3) 0.28324(12) 0.5227(3) 0.0443(7) Uani 1 1 d . . . . .
H11 H 0.4388 0.2590 0.6066 0.053 Uiso 1 1 calc R . . . .
C7 C 0.3191(3) 0.41115(13) -0.2111(3) 0.0407(6) Uani 1 1 d . . . . .
H7 H 0.3564 0.3904 -0.2879 0.049 Uiso 1 1 calc R . . . .
C4 C 0.2057(3) 0.47177(11) 0.0173(4) 0.0415(6) Uani 1 1 d . . . . .
H4 H 0.1677 0.4924 0.0937 0.050 Uiso 1 1 calc R . . . .
C10 C 0.4492(3) 0.31321(12) 0.4174(4) 0.0420(6) Uani 1 1 d . . . . .
H10 H 0.5511 0.3109 0.4348 0.050 Uiso 1 1 calc R . . . .
C16 C -0.2446(3) 0.32482(12) 0.1160(4) 0.0408(6) Uani 1 1 d . . . . .
H16 H -0.2919 0.3069 0.1887 0.049 Uiso 1 1 calc R . . . .
C18 C -0.2526(3) 0.36025(14) -0.1582(4) 0.0470(7) Uani 1 1 d . . . . .
H18 H -0.3052 0.3673 -0.2692 0.056 Uiso 1 1 calc R . . . .
C2 C 0.3319(3) 0.47148(13) -0.2038(4) 0.0426(7) Uani 1 1 d . . . . .
C19 C -0.1054(3) 0.37669(12) -0.1035(3) 0.0382(6) Uani 1 1 d . . . . .
H19 H -0.0592 0.3941 -0.1781 0.046 Uiso 1 1 calc R . . . .
C12 C 0.2326(3) 0.28947(11) 0.5027(3) 0.0386(6) Uani 1 1 d . . . . .
H12 H 0.1885 0.2698 0.5756 0.046 Uiso 1 1 calc R . . . .
C17 C -0.3218(3) 0.33350(13) -0.0498(4) 0.0468(7) Uani 1 1 d . . . . .
H17 H -0.4196 0.3214 -0.0883 0.056 Uiso 1 1 calc R . . . .
C3 C 0.2740(3) 0.50136(12) -0.0893(4) 0.0490(7) Uani 1 1 d . . . . .
H3 H 0.2809 0.5419 -0.0837 0.059 Uiso 1 1 calc R . . . .
C22 C -0.0168(3) 0.40266(13) 0.4357(4) 0.0469(7) Uani 1 1 d . . . . .
H22A H -0.1171 0.4141 0.4265 0.070 Uiso 1 1 calc GR . . . .
H22B H 0.0269 0.4295 0.3731 0.070 Uiso 1 1 calc GR . . . .
H22C H 0.0385 0.4031 0.5520 0.070 Uiso 1 1 calc GR . . . .
C21 C -0.0844(4) 0.29792(16) 0.4658(4) 0.0579(9) Uani 1 1 d . . . . .
H21A H -0.0844 0.2590 0.4222 0.087 Uiso 1 1 calc GR . . . .
H21B H -0.1842 0.3098 0.4574 0.087 Uiso 1 1 calc GR . . . .
H21C H -0.0283 0.2987 0.5818 0.087 Uiso 1 1 calc GR . . . .
C1 C 0.4051(4) 0.50315(18) -0.3216(5) 0.0703(11) Uani 1 1 d . . . . .
H1A H 0.3534 0.4944 -0.4362 0.105 Uiso 1 1 calc GR . . . .
H1B H 0.5060 0.4906 -0.3003 0.105 Uiso 1 1 calc GR . . . .
H1C H 0.4022 0.5445 -0.3031 0.105 Uiso 1 1 calc GR . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.444(3) . ?
N1 C8 1.407(3) . ?
N1 C20 1.413(3) . ?
C5 C6 1.386(3) . ?
C5 C4 1.381(4) . ?
C15 C20 1.408(3) . ?
C15 C14 1.522(4) . ?
C15 C16 1.391(3) . ?
C8 C13 1.413(3) . ?
C8 C9 1.397(3) . ?
C20 C19 1.398(3) . ?
C13 C14 1.523(3) . ?
C13 C12 1.395(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(4) . ?
C14 C22 1.555(4) . ?
C14 C21 1.535(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.376(4) . ?
C11 C12 1.384(4) . ?
C7 H7 0.9300 . ?
C7 C2 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.393(4) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(4) . ?
C18 C17 1.379(4) . ?
C2 C3 1.387(4) . ?
C2 C1 1.514(4) . ?
C19 H19 0.9300 . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C5 118.89(19) . . ?
C8 N1 C20 118.76(19) . . ?
C20 N1 C5 118.96(19) . . ?
C6 C5 N1 121.4(2) . . ?
C4 C5 N1 118.8(2) . . ?
C4 C5 C6 119.8(2) . . ?
C20 C15 C14 118.2(2) . . ?
C16 C15 C20 118.1(2) . . ?
C16 C15 C14 123.5(2) . . ?
N1 C8 C13 118.9(2) . . ?
C9 C8 N1 121.4(2) . . ?
C9 C8 C13 119.7(2) . . ?
C15 C20 N1 119.0(2) . . ?
C19 C20 N1 121.0(2) . . ?
C19 C20 C15 120.0(2) . . ?
C8 C13 C14 117.9(2) . . ?
C12 C13 C8 118.2(2) . . ?
C12 C13 C14 123.6(2) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C15 C14 C13 108.00(19) . . ?
C15 C14 C22 107.4(2) . . ?
C15 C14 C21 113.0(2) . . ?
C13 C14 C22 107.6(2) . . ?
C13 C14 C21 112.1(2) . . ?
C21 C14 C22 108.5(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C6 C7 H7 119.5 . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 H7 119.5 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 H16 119.1 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(3) . . ?
C7 C2 C3 118.4(2) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 121.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C13 C12 H12 119.2 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 H12 119.2 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C5 C6 C7 -179.5(2) . . . . ?
N1 C5 C4 C3 179.5(2) . . . . ?
N1 C8 C13 C14 -11.6(3) . . . . ?
N1 C8 C13 C12 173.7(2) . . . . ?
N1 C8 C9 C10 -175.9(2) . . . . ?
N1 C20 C19 C18 178.0(2) . . . . ?
C5 N1 C8 C13 176.7(2) . . . . ?
C5 N1 C8 C9 -3.2(3) . . . . ?
C5 N1 C20 C15 -175.1(2) . . . . ?
C5 N1 C20 C19 5.3(3) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C15 C20 C19 C18 -1.6(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C8 N1 C5 C6 74.3(3) . . . . ?
C8 N1 C5 C4 -105.4(3) . . . . ?
C8 N1 C20 C15 25.9(3) . . . . ?
C8 N1 C20 C19 -153.7(2) . . . . ?
C8 C13 C14 C15 41.4(3) . . . . ?
C8 C13 C14 C22 -74.2(3) . . . . ?
C8 C13 C14 C21 166.6(2) . . . . ?
C8 C13 C12 C11 3.6(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C20 N1 C5 C6 -84.7(3) . . . . ?
C20 N1 C5 C4 95.7(3) . . . . ?
C20 N1 C8 C13 -24.2(3) . . . . ?
C20 N1 C8 C9 155.8(2) . . . . ?
C20 C15 C14 C13 -39.8(3) . . . . ?
C20 C15 C14 C22 75.9(3) . . . . ?
C20 C15 C14 C21 -164.5(2) . . . . ?
C20 C15 C16 C17 -2.4(4) . . . . ?
C13 C8 C9 C10 4.2(4) . . . . ?
C6 C5 C4 C3 -0.2(4) . . . . ?
C6 C7 C2 C3 -0.6(4) . . . . ?
C6 C7 C2 C1 -179.4(3) . . . . ?
C14 C15 C20 N1 8.5(3) . . . . ?
C14 C15 C20 C19 -171.9(2) . . . . ?
C14 C15 C16 C17 172.5(2) . . . . ?
C14 C13 C12 C11 -170.8(2) . . . . ?
C9 C8 C13 C14 168.4(2) . . . . ?
C9 C8 C13 C12 -6.4(3) . . . . ?
C7 C2 C3 C4 0.6(4) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C16 C15 C20 N1 -176.3(2) . . . . ?
C16 C15 C20 C19 3.3(3) . . . . ?
C16 C15 C14 C13 145.3(2) . . . . ?
C16 C15 C14 C22 -99.0(3) . . . . ?
C16 C15 C14 C21 20.6(4) . . . . ?
C19 C18 C17 C16 2.1(4) . . . . ?
C12 C13 C14 C15 -144.1(2) . . . . ?
C12 C13 C14 C22 100.2(3) . . . . ?
C12 C13 C14 C21 -19.0(4) . . . . ?
C12 C11 C10 C9 -3.7(4) . . . . ?
C17 C18 C19 C20 -1.2(4) . . . . ?
C1 C2 C3 C4 179.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
