# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_3ab
_database_code_depnum_ccdc_archive 'CCDC 1905948'
loop_
_audit_author_name
_audit_author_address
'Yaping Shang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4-fluoro-1-methyl-2,3-diphenyl-1H-indole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 F N'
_chemical_formula_sum            'C21 H16 F N'
_chemical_formula_weight         301.35

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8096(5)
_cell_length_b                   9.0152(5)
_cell_length_c                   10.3747(6)
_cell_angle_alpha                74.507(3)
_cell_angle_beta                 77.133(3)
_cell_angle_gamma                80.906(3)
_cell_volume                     769.81(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    9394
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31578
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3565
_reflns_number_gt                2868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0987P)²+0.3444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.23(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3565
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1832
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.16585(12) 0.27070(14) 0.73123(11) 0.0329(3) Uani 1 1 d . . .
N1 N 0.70036(17) 0.19862(17) 0.57272(14) 0.0231(3) Uani 1 1 d . . .
C1 C 0.5909(2) 0.20780(19) 0.68865(17) 0.0226(4) Uani 1 1 d . . .
C2 C 0.4411(2) 0.23904(18) 0.65267(17) 0.0215(4) Uani 1 1 d . . .
C3 C 0.46398(19) 0.25004(18) 0.50902(16) 0.0211(4) Uani 1 1 d . . .
C4 C 0.62321(19) 0.22378(18) 0.46453(16) 0.0209(4) Uani 1 1 d . . .
C5 C 0.3134(2) 0.2457(2) 0.75881(18) 0.0249(4) Uani 1 1 d . . .
C6 C 0.3308(2) 0.2282(2) 0.89050(18) 0.0301(4) Uani 1 1 d . . .
H6A H 0.2414 0.2343 0.9604 0.036 Uiso 1 1 calc R . .
C7 C 0.4815(2) 0.2014(2) 0.92104(19) 0.0327(4) Uani 1 1 d . . .
H7A H 0.4933 0.1911 1.0119 0.039 Uiso 1 1 calc R . .
C8 C 0.6129(2) 0.1895(2) 0.82180(18) 0.0288(4) Uani 1 1 d . . .
H8A H 0.7148 0.1697 0.8430 0.035 Uiso 1 1 calc R . .
C9 C 0.8679(2) 0.1690(2) 0.56870(19) 0.0282(4) Uani 1 1 d . . .
H9A H 0.8890 0.1558 0.6602 0.042 Uiso 1 1 calc R . .
H9B H 0.9197 0.2566 0.5062 0.042 Uiso 1 1 calc R . .
H9C H 0.9083 0.0746 0.5370 0.042 Uiso 1 1 calc R . .
C10 C 0.70768(19) 0.2266(2) 0.32383(17) 0.0227(4) Uani 1 1 d . . .
C11 C 0.8062(2) 0.0990(2) 0.29150(19) 0.0276(4) Uani 1 1 d . . .
H11A H 0.8210 0.0079 0.3610 0.033 Uiso 1 1 calc R . .
C12 C 0.8827(2) 0.1049(2) 0.1580(2) 0.0335(4) Uani 1 1 d . . .
H12A H 0.9506 0.0181 0.1369 0.040 Uiso 1 1 calc R . .
C13 C 0.8606(2) 0.2367(3) 0.05526(19) 0.0342(5) Uani 1 1 d . . .
H13A H 0.9139 0.2406 -0.0357 0.041 Uiso 1 1 calc R . .
C14 C 0.7604(2) 0.3628(2) 0.08604(19) 0.0347(5) Uani 1 1 d . . .
H14A H 0.7435 0.4525 0.0157 0.042 Uiso 1 1 calc R . .
C15 C 0.6845(2) 0.3582(2) 0.21985(19) 0.0283(4) Uani 1 1 d . . .
H15A H 0.6165 0.4451 0.2405 0.034 Uiso 1 1 calc R . .
C16 C 0.34479(19) 0.28271(19) 0.42273(16) 0.0215(4) Uani 1 1 d . . .
C17 C 0.3421(2) 0.1861(2) 0.33821(17) 0.0245(4) Uani 1 1 d . . .
H17A H 0.4158 0.0969 0.3384 0.029 Uiso 1 1 calc R . .
C18 C 0.2326(2) 0.2193(2) 0.25388(18) 0.0289(4) Uani 1 1 d . . .
H18A H 0.2316 0.1523 0.1974 0.035 Uiso 1 1 calc R . .
C19 C 0.1250(2) 0.3494(2) 0.25155(19) 0.0326(5) Uani 1 1 d . . .
H19A H 0.0508 0.3720 0.1933 0.039 Uiso 1 1 calc R . .
C20 C 0.1264(2) 0.4464(2) 0.3350(2) 0.0326(4) Uani 1 1 d . . .
H20A H 0.0529 0.5358 0.3338 0.039 Uiso 1 1 calc R . .
C21 C 0.2350(2) 0.4132(2) 0.42049(18) 0.0273(4) Uani 1 1 d . . .
H21A H 0.2346 0.4798 0.4778 0.033 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 C5 1.365(2) . ?
N1 C1 1.376(2) . ?
N1 C4 1.389(2) . ?
N1 C9 1.451(2) . ?
C1 C8 1.400(2) . ?
C1 C2 1.416(2) . ?
C2 C5 1.394(2) . ?
C2 C3 1.437(2) . ?
C3 C4 1.379(2) . ?
C3 C16 1.473(2) . ?
C4 C10 1.479(2) . ?
C5 C6 1.373(3) . ?
C6 C7 1.402(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.396(2) . ?
C10 C15 1.397(2) . ?
C11 C12 1.390(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.397(2) . ?
C16 C21 1.399(2) . ?
C17 C18 1.389(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.392(3) . ?
C20 H20A 0.9500 . ?
C21 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 C4 108.70(14) . . ?
C1 N1 C9 124.02(14) . . ?
C4 N1 C9 127.28(15) . . ?
N1 C1 C8 129.35(16) . . ?
N1 C1 C2 107.78(14) . . ?
C8 C1 C2 122.87(16) . . ?
C5 C2 C1 116.29(15) . . ?
C5 C2 C3 136.33(16) . . ?
C1 C2 C3 107.33(15) . . ?
C4 C3 C2 106.32(14) . . ?
C4 C3 C16 125.37(15) . . ?
C2 C3 C16 128.31(15) . . ?
C3 C4 N1 109.87(15) . . ?
C3 C4 C10 127.66(15) . . ?
N1 C4 C10 122.42(15) . . ?
F1 C5 C6 118.67(16) . . ?
F1 C5 C2 119.03(15) . . ?
C6 C5 C2 122.30(17) . . ?
C5 C6 C7 119.51(17) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C8 C7 C6 121.31(17) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C1 117.67(17) . . ?
C7 C8 H8A 121.2 . . ?
C1 C8 H8A 121.2 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 119.11(16) . . ?
C11 C10 C4 121.65(15) . . ?
C15 C10 C4 119.21(16) . . ?
C12 C11 C10 120.21(17) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C13 C12 C11 120.43(18) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 119.73(17) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 120.11(18) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 C10 120.39(18) . . ?
C14 C15 H15A 119.8 . . ?
C10 C15 H15A 119.8 . . ?
C17 C16 C21 118.58(16) . . ?
C17 C16 C3 120.52(15) . . ?
C21 C16 C3 120.87(15) . . ?
C18 C17 C16 120.54(17) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C17 120.53(17) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 119.51(17) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C21 C20 C19 120.28(18) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C20 C21 C16 120.55(17) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 119.7 . . ?

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
C4 N1 C1 C8 179.53(17) . . . . ?
C9 N1 C1 C8 -1.1(3) . . . . ?
C4 N1 C1 C2 0.18(18) . . . . ?
C9 N1 C1 C2 179.55(15) . . . . ?
N1 C1 C2 C5 177.24(14) . . . . ?
C8 C1 C2 C5 -2.2(3) . . . . ?
N1 C1 C2 C3 -0.54(18) . . . . ?
C8 C1 C2 C3 -179.94(15) . . . . ?
C5 C2 C3 C4 -176.43(19) . . . . ?
C1 C2 C3 C4 0.69(18) . . . . ?
C5 C2 C3 C16 3.6(3) . . . . ?
C1 C2 C3 C16 -179.25(16) . . . . ?
C2 C3 C4 N1 -0.59(18) . . . . ?
C16 C3 C4 N1 179.35(15) . . . . ?
C2 C3 C4 C10 -178.22(16) . . . . ?
C16 C3 C4 C10 1.7(3) . . . . ?
C1 N1 C4 C3 0.27(19) . . . . ?
C9 N1 C4 C3 -179.08(16) . . . . ?
C1 N1 C4 C10 178.05(15) . . . . ?
C9 N1 C4 C10 -1.3(3) . . . . ?
C1 C2 C5 F1 -178.00(14) . . . . ?
C3 C2 C5 F1 -1.1(3) . . . . ?
C1 C2 C5 C6 2.1(3) . . . . ?
C3 C2 C5 C6 178.99(18) . . . . ?
F1 C5 C6 C7 179.54(17) . . . . ?
C2 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C1 1.0(3) . . . . ?
N1 C1 C8 C7 -178.59(18) . . . . ?
C2 C1 C8 C7 0.7(3) . . . . ?
C3 C4 C10 C11 -123.1(2) . . . . ?
N1 C4 C10 C11 59.5(2) . . . . ?
C3 C4 C10 C15 54.8(2) . . . . ?
N1 C4 C10 C15 -122.58(18) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C4 C10 C11 C12 179.39(16) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C4 C10 C15 C14 -178.83(16) . . . . ?
C4 C3 C16 C17 51.4(2) . . . . ?
C2 C3 C16 C17 -128.65(19) . . . . ?
C4 C3 C16 C21 -126.64(19) . . . . ?
C2 C3 C16 C21 53.3(2) . . . . ?
C21 C16 C17 C18 0.0(3) . . . . ?
C3 C16 C17 C18 -178.12(15) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C17 C16 C21 C20 -0.5(3) . . . . ?
C3 C16 C21 C20 177.65(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.303
####################################################################### 
# 
# 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_full
_database_code_depnum_ccdc_archive 'CCDC 1906495'
loop_
_audit_author_name
_audit_author_address
'Yaping Shang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 3-acetyl-1-methyl-2-phenyl-1H-indole-5-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.34

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcm
_symmetry_space_group_name_Hall  '-P 2c 2b'

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

_cell_length_a                   8.8963(11)
_cell_length_b                   24.680(3)
_cell_length_c                   21.421(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4703.2(10)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3237
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.25

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30645
_diffrn_reflns_av_R_equivalents  0.1440
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4191
_reflns_number_gt                2569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0760P)²+26.5794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4191
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1834
_refine_ls_R_factor_gt           0.1253
_refine_ls_wR_factor_ref         0.3240
_refine_ls_wR_factor_gt          0.2799
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3977(6) 0.03221(18) 0.0869(2) 0.0589(14) Uani 1 1 d . . .
O2 O 0.5423(8) 0.2207(2) 0.0794(3) 0.0727(17) Uani 1 1 d . . .
O3 O 0.7774(6) 0.25236(19) 0.0849(2) 0.0680(16) Uani 1 1 d . . .
O4 O 1.0789(6) 0.4788(2) 0.2500 0.0405(15) Uani 1 2 d S . .
O5 O 0.6873(7) 0.2596(2) 0.2500 0.0439(16) Uani 1 2 d S . .
O6 O 0.9283(8) 0.2903(2) 0.2500 0.0469(17) Uani 1 2 d S . .
N1 N 0.9019(6) 0.0014(2) 0.0821(2) 0.0415(13) Uani 1 1 d . . .
N2 N 0.5725(7) 0.5120(3) 0.2500 0.0298(15) Uani 1 2 d S . .
C1 C 0.8657(8) 0.0566(3) 0.0819(3) 0.0453(17) Uani 1 1 d . . .
C2 C 0.7096(7) 0.0610(2) 0.0827(3) 0.0352(14) Uani 1 1 d . . .
C3 C 0.6455(7) 0.0068(2) 0.0834(3) 0.0350(14) Uani 1 1 d . . .
C4 C 0.7684(6) -0.0279(2) 0.0824(3) 0.0313(13) Uani 1 1 d . . .
C5 C 0.9660(9) 0.1006(3) 0.0811(3) 0.0524(18) Uani 1 1 d . . .
H5A H 1.0719 0.0957 0.0808 0.063 Uiso 1 1 calc R . .
C6 C 0.9017(9) 0.1505(3) 0.0809(3) 0.059(2) Uani 1 1 d . . .
H6A H 0.9653 0.1814 0.0801 0.070 Uiso 1 1 calc R . .
C7 C 0.7483(8) 0.1585(2) 0.0817(3) 0.0426(16) Uani 1 1 d . . .
C8 C 0.6493(9) 0.1138(3) 0.0825(3) 0.0497(18) Uani 1 1 d . . .
H8A H 0.5436 0.1193 0.0829 0.060 Uiso 1 1 calc R . .
C9 C 1.0542(7) -0.0197(3) 0.0814(3) 0.058(2) Uani 1 1 d . . .
H9A H 1.1208 0.0063 0.0606 0.086 Uiso 1 1 calc R . .
H9B H 1.0561 -0.0542 0.0587 0.086 Uiso 1 1 calc R . .
H9C H 1.0885 -0.0255 0.1244 0.086 Uiso 1 1 calc R . .
C10 C 0.4901(8) -0.0058(3) 0.0859(3) 0.0395(15) Uani 1 1 d . . .
C11 C 0.4308(8) -0.0620(3) 0.0890(3) 0.0469(17) Uani 1 1 d . . .
H11A H 0.4031 -0.0742 0.0470 0.070 Uiso 1 1 calc R . .
H11B H 0.3420 -0.0629 0.1160 0.070 Uiso 1 1 calc R . .
H11C H 0.5082 -0.0861 0.1060 0.070 Uiso 1 1 calc R . .
C12 C 0.6803(11) 0.2124(3) 0.0818(3) 0.056(2) Uani 1 1 d . . .
C13 C 0.7230(11) 0.3067(3) 0.0860(4) 0.074(3) Uani 1 1 d . . .
H13A H 0.6629 0.3135 0.0485 0.111 Uiso 1 1 calc R . .
H13B H 0.8082 0.3319 0.0871 0.111 Uiso 1 1 calc R . .
H13C H 0.6605 0.3121 0.1232 0.111 Uiso 1 1 calc R . .
C14 C 0.7765(7) -0.0880(2) 0.0819(3) 0.0370(15) Uani 1 1 d . . .
C15 C 0.8322(7) -0.1168(3) 0.1334(3) 0.0448(17) Uani 1 1 d . . .
H15A H 0.8637 -0.0979 0.1698 0.054 Uiso 1 1 calc R . .
C16 C 0.8415(9) -0.1730(3) 0.1314(4) 0.062(2) Uani 1 1 d . . .
H16A H 0.8820 -0.1926 0.1656 0.074 Uiso 1 1 calc R . .
C17 C 0.7913(11) -0.1997(3) 0.0792(4) 0.077(3) Uani 1 1 d . . .
H17A H 0.7987 -0.2380 0.0778 0.092 Uiso 1 1 calc R . .
C18 C 0.7312(10) -0.1729(3) 0.0294(4) 0.070(2) Uani 1 1 d . . .
H18A H 0.6956 -0.1927 -0.0056 0.084 Uiso 1 1 calc R . .
C19 C 0.7218(9) -0.1164(3) 0.0297(3) 0.0553(19) Uani 1 1 d . . .
H19A H 0.6794 -0.0976 -0.0047 0.066 Uiso 1 1 calc R . .
C20 C 0.6028(8) 0.4573(3) 0.2500 0.0261(17) Uani 1 2 d S . .
C21 C 0.7619(7) 0.4512(3) 0.2500 0.0221(17) Uani 1 2 d S . .
C22 C 0.8288(8) 0.5045(3) 0.2500 0.0261(17) Uani 1 2 d S . .
C23 C 0.7055(9) 0.5412(3) 0.2500 0.034(2) Uani 1 2 d S . .
C24 C 0.8209(9) 0.3983(3) 0.2500 0.0269(18) Uani 1 2 d S . .
H24A H 0.9265 0.3927 0.2500 0.032 Uiso 1 2 calc SR . .
C25 C 0.7246(10) 0.3553(3) 0.2500 0.0308(19) Uani 1 2 d S . .
C26 C 0.5689(11) 0.3611(3) 0.2500 0.042(2) Uani 1 2 d S . .
H26A H 0.5054 0.3301 0.2500 0.051 Uiso 1 2 d SR . .
C27 C 0.5063(10) 0.4132(4) 0.2500 0.040(2) Uani 1 2 d S . .
H27A H 0.4004 0.4184 0.2500 0.048 Uiso 1 2 d SR . .
C28 C 0.4236(9) 0.5346(4) 0.2500 0.039(2) Uani 1 2 d S . .
H28A H 0.3705 0.5215 0.2130 0.047 Uiso 1 1 d R . .
H28B H 0.4296 0.5741 0.2500 0.047 Uiso 1 2 d SR . .
C29 C 0.9878(10) 0.5161(3) 0.2500 0.035(2) Uani 1 2 d S . .
C30 C 1.0437(10) 0.5749(3) 0.2500 0.041(2) Uani 1 2 d S . .
H30A H 1.1522 0.5763 0.2445 0.049 Uiso 0.50 1 d PR . .
H30B H 1.0127 0.5926 0.2877 0.049 Uiso 1 1 d R . .
C31 C 0.7936(11) 0.2995(3) 0.2500 0.035(2) Uani 1 2 d S . .
C32 C 0.7503(14) 0.2041(3) 0.2500 0.059(3) Uani 1 2 d S . .
H32A H 0.6704 0.1782 0.2440 0.071 Uiso 0.50 1 d PR . .
H32B H 0.8062 0.1979 0.2123 0.071 Uiso 1 1 d R . .
C33 C 0.7034(10) 0.6010(3) 0.2500 0.035(2) Uani 1 2 d S . .
C34 C 0.6930(11) 0.6292(3) 0.1963(4) 0.072(3) Uani 1 1 d . . .
H34A H 0.6888 0.6099 0.1579 0.087 Uiso 1 1 d R . .
C35 C 0.6872(12) 0.6859(3) 0.1962(5) 0.090(3) Uani 1 1 d . . .
H35A H 0.6812 0.7050 0.1577 0.108 Uiso 1 1 d R . .
C36 C 0.6947(14) 0.7128(5) 0.2500 0.070(3) Uani 1 2 d S . .
H36A H 0.7018 0.7512 0.2500 0.084 Uiso 1 2 d SR . .


_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 C10 1.248(8) . ?
O2 C12 1.245(10) . ?
O3 C12 1.312(9) . ?
O3 C13 1.426(9) . ?
O4 C29 1.228(10) . ?
O5 C31 1.365(10) . ?
O5 C32 1.481(11) . ?
O6 C31 1.219(11) . ?
N1 C4 1.390(7) . ?
N1 C1 1.399(8) . ?
N1 C9 1.452(8) . ?
N2 C20 1.376(10) . ?
N2 C23 1.386(11) . ?
N2 C28 1.438(10) . ?
C1 C2 1.393(9) . ?
C1 C5 1.405(9) . ?
C2 C8 1.411(9) . ?
C2 C3 1.453(8) . ?
C3 C4 1.389(8) . ?
C3 C10 1.418(9) . ?
C4 C14 1.486(8) . ?
C5 C6 1.359(10) . ?
C5 H5A 0.9500 . ?
C6 C7 1.378(10) . ?
C6 H6A 0.9500 . ?
C7 C8 1.410(9) . ?
C7 C12 1.464(10) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.486(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.403(8) . ?
C14 C19 1.407(9) . ?
C15 C16 1.390(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.370(11) . ?
C16 H16A 0.9500 . ?
C17 C18 1.364(11) . ?
C17 H17A 0.9500 . ?
C18 C19 1.396(10) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C27 1.386(11) . ?
C20 C21 1.424(10) . ?
C21 C24 1.405(10) . ?
C21 C22 1.444(10) . ?
C22 C23 1.423(11) . ?
C22 C29 1.444(11) . ?
C23 C33 1.476(11) . ?
C24 C25 1.365(11) . ?
C24 H24A 0.9500 . ?
C25 C26 1.393(13) . ?
C25 C31 1.506(12) . ?
C26 C27 1.403(13) . ?
C26 H26A 0.9497 . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9782 . ?
C28 H28B 0.9768 . ?
C29 C30 1.533(11) . ?
C30 H30A 0.9722 . ?
C30 H30B 0.9584 . ?
C32 H32A 0.9650 . ?
C32 H32B 0.9605 . ?
C33 C34 1.349(8) . ?
C33 C34 1.349(8) 6_556 ?
C34 C35 1.401(10) . ?
C34 H34A 0.9507 . ?
C35 C36 1.332(10) . ?
C35 H35A 0.9500 . ?
C36 C35 1.332(10) 6_556 ?
C36 H36A 0.9498 . ?

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
C12 O3 C13 118.9(7) . . ?
C31 O5 C32 113.9(7) . . ?
C4 N1 C1 108.0(5) . . ?
C4 N1 C9 127.7(5) . . ?
C1 N1 C9 124.3(6) . . ?
C20 N2 C23 110.1(6) . . ?
C20 N2 C28 124.2(7) . . ?
C23 N2 C28 125.7(7) . . ?
C2 C1 N1 107.8(5) . . ?
C2 C1 C5 124.9(7) . . ?
N1 C1 C5 127.3(7) . . ?
C1 C2 C8 116.8(6) . . ?
C1 C2 C3 108.6(5) . . ?
C8 C2 C3 134.5(6) . . ?
C4 C3 C10 129.2(6) . . ?
C4 C3 C2 105.0(5) . . ?
C10 C3 C2 125.8(6) . . ?
C3 C4 N1 110.6(5) . . ?
C3 C4 C14 130.9(5) . . ?
N1 C4 C14 118.5(5) . . ?
C6 C5 C1 115.7(7) . . ?
C6 C5 H5A 122.1 . . ?
C1 C5 H5A 122.1 . . ?
C5 C6 C7 123.0(7) . . ?
C5 C6 H6A 118.5 . . ?
C7 C6 H6A 118.5 . . ?
C6 C7 C8 120.5(7) . . ?
C6 C7 C12 122.6(7) . . ?
C8 C7 C12 116.9(7) . . ?
C7 C8 C2 119.0(7) . . ?
C7 C8 H8A 120.5 . . ?
C2 C8 H8A 120.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C3 118.5(6) . . ?
O1 C10 C11 117.9(6) . . ?
C3 C10 C11 123.6(6) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 122.0(8) . . ?
O2 C12 C7 123.8(7) . . ?
O3 C12 C7 114.3(8) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.6(6) . . ?
C15 C14 C4 121.2(5) . . ?
C19 C14 C4 119.1(6) . . ?
C16 C15 C14 120.1(6) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C17 C16 C15 119.1(7) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C18 C17 C16 122.2(7) . . ?
C18 C17 H17A 118.9 . . ?
C16 C17 H17A 118.9 . . ?
C17 C18 C19 120.2(8) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C14 118.7(7) . . ?
C18 C19 H19A 120.6 . . ?
C14 C19 H19A 120.6 . . ?
N2 C20 C27 130.4(7) . . ?
N2 C20 C21 107.4(6) . . ?
C27 C20 C21 122.2(7) . . ?
C24 C21 C20 118.0(7) . . ?
C24 C21 C22 133.8(6) . . ?
C20 C21 C22 108.2(7) . . ?
C23 C22 C21 105.3(6) . . ?
C23 C22 C29 128.9(8) . . ?
C21 C22 C29 125.8(7) . . ?
N2 C23 C22 109.0(7) . . ?
N2 C23 C33 120.7(7) . . ?
C22 C23 C33 130.3(8) . . ?
C25 C24 C21 119.2(7) . . ?
C25 C24 H24A 120.4 . . ?
C21 C24 H24A 120.4 . . ?
C24 C25 C26 123.0(8) . . ?
C24 C25 C31 117.1(8) . . ?
C26 C25 C31 120.0(7) . . ?
C27 C26 C25 119.3(8) . . ?
C27 C26 H26A 120.1 . . ?
C25 C26 H26A 120.6 . . ?
C20 C27 C26 118.3(8) . . ?
C20 C27 H27A 120.6 . . ?
C26 C27 H27A 121.0 . . ?
N2 C28 H28A 108.5 . . ?
N2 C28 H28B 109.7 . . ?
H28A C28 H28B 111.0 . . ?
O4 C29 C22 119.8(7) . . ?
O4 C29 C30 119.7(7) . . ?
C22 C29 C30 120.5(8) . . ?
C29 C30 H30A 110.8 . . ?
C29 C30 H30B 109.8 . . ?
H30A C30 H30B 111.9 . . ?
O6 C31 O5 123.2(8) . . ?
O6 C31 C25 124.8(7) . . ?
O5 C31 C25 112.1(8) . . ?
O5 C32 H32A 109.6 . . ?
O5 C32 H32B 110.1 . . ?
H32A C32 H32B 99.4 . . ?
C34 C33 C34 117.2(9) . 6_556 ?
C34 C33 C23 121.2(4) . . ?
C34 C33 C23 121.2(4) 6_556 . ?
C33 C34 C35 121.3(8) . . ?
C33 C34 H34A 118.7 . . ?
C35 C34 H34A 119.9 . . ?
C36 C35 C34 119.7(9) . . ?
C36 C35 H35A 120.5 . . ?
C34 C35 H35A 119.8 . . ?
C35 C36 C35 119.9(11) . 6_556 ?
C35 C36 H36A 120.1 . . ?
C35 C36 H36A 120.1 6_556 . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_3aj
_database_code_depnum_ccdc_archive 'CCDC 1905949'
loop_
_audit_author_name
_audit_author_address
'Yaping Shang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'4-(5-acetoxy-1-ethyl-3-methyl-1H-indol-2-yl)phenyl acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.0197(2)
_cell_length_b                   9.5895(3)
_cell_length_c                   20.6274(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.511(2)
_cell_angle_gamma                90.00
_cell_volume                     1778.63(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3594
_cell_measurement_theta_min      4.9120
_cell_measurement_theta_max      73.2630

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7562
_exptl_absorpt_correction_T_max  0.8661
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6557
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         69.99
_reflns_number_total             3348
_reflns_number_gt                3026
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.8112P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3348
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.28835(13) 0.62763(12) 0.48346(6) 0.0158(3) Uani 1 1 d . . .
O1 O 0.28791(12) 1.02217(11) 0.67697(5) 0.0241(3) Uani 1 1 d . . .
O2 O 0.53383(12) 1.00616(12) 0.70505(6) 0.0304(3) Uani 1 1 d . . .
O3 O 0.13479(12) 0.00419(10) 0.38299(5) 0.0207(2) Uani 1 1 d . . .
O4 O 0.06893(14) 0.12797(11) 0.29228(5) 0.0292(3) Uani 1 1 d . . .
C1 C 0.30013(15) 0.73865(15) 0.52586(6) 0.0164(3) Uani 1 1 d . . .
C2 C 0.27164(14) 0.68979(15) 0.58842(7) 0.0169(3) Uani 1 1 d . . .
C3 C 0.24014(15) 0.54371(15) 0.58264(7) 0.0174(3) Uani 1 1 d . . .
C4 C 0.24956(15) 0.50969(14) 0.51827(7) 0.0160(3) Uani 1 1 d . . .
C5 C 0.32815(15) 0.87887(15) 0.51355(7) 0.0184(3) Uani 1 1 d . . .
H5A H 0.3474 0.9097 0.4713 0.022 Uiso 1 1 calc R . .
C6 C 0.32697(15) 0.97156(15) 0.56497(7) 0.0202(3) Uani 1 1 d . . .
H6A H 0.3448 1.0679 0.5582 0.024 Uiso 1 1 calc R . .
C7 C 0.29950(15) 0.92319(15) 0.62675(7) 0.0198(3) Uani 1 1 d . . .
C8 C 0.27225(15) 0.78541(15) 0.63992(7) 0.0190(3) Uani 1 1 d . . .
H8A H 0.2544 0.7559 0.6826 0.023 Uiso 1 1 calc R . .
C9 C 0.27169(16) 0.64514(15) 0.41259(6) 0.0188(3) Uani 1 1 d . . .
H9A H 0.2076 0.7271 0.4020 0.023 Uiso 1 1 calc R . .
H9B H 0.2208 0.5621 0.3929 0.023 Uiso 1 1 calc R . .
C10 C 0.41876(18) 0.66482(17) 0.38252(7) 0.0255(3) Uani 1 1 d . . .
H10A H 0.4003 0.6759 0.3354 0.038 Uiso 1 1 calc R . .
H10B H 0.4820 0.5830 0.3919 0.038 Uiso 1 1 calc R . .
H10C H 0.4688 0.7482 0.4009 0.038 Uiso 1 1 calc R . .
C11 C 0.20457(17) 0.44860(16) 0.63690(7) 0.0234(3) Uani 1 1 d . . .
H11A H 0.1877 0.3540 0.6199 0.035 Uiso 1 1 calc R . .
H11B H 0.1148 0.4818 0.6559 0.035 Uiso 1 1 calc R . .
H11C H 0.2880 0.4478 0.6704 0.035 Uiso 1 1 calc R . .
C12 C 0.41444(16) 1.05458(15) 0.71408(7) 0.0203(3) Uani 1 1 d . . .
C13 C 0.38223(18) 1.15656(17) 0.76556(7) 0.0265(3) Uani 1 1 d . . .
H13A H 0.4744 1.1789 0.7919 0.040 Uiso 1 1 calc R . .
H13B H 0.3104 1.1161 0.7934 0.040 Uiso 1 1 calc R . .
H13C H 0.3407 1.2419 0.7453 0.040 Uiso 1 1 calc R . .
C14 C 0.22412(15) 0.37454(14) 0.48542(7) 0.0160(3) Uani 1 1 d . . .
C15 C 0.32769(15) 0.31999(14) 0.44486(7) 0.0172(3) Uani 1 1 d . . .
H15A H 0.4186 0.3679 0.4408 0.021 Uiso 1 1 calc R . .
C16 C 0.29925(16) 0.19718(15) 0.41070(7) 0.0186(3) Uani 1 1 d . . .
H16A H 0.3698 0.1604 0.3834 0.022 Uiso 1 1 calc R . .
C17 C 0.16597(16) 0.12922(14) 0.41716(7) 0.0178(3) Uani 1 1 d . . .
C18 C 0.06430(15) 0.17608(15) 0.45875(7) 0.0192(3) Uani 1 1 d . . .
H18A H -0.0241 0.1249 0.4641 0.023 Uiso 1 1 calc R . .
C19 C 0.09354(15) 0.29933(15) 0.49274(7) 0.0188(3) Uani 1 1 d . . .
H19A H 0.0240 0.3330 0.5213 0.023 Uiso 1 1 calc R . .
C20 C 0.08598(16) 0.01782(15) 0.31853(7) 0.0202(3) Uani 1 1 d . . .
C21 C 0.05933(18) -0.12279(16) 0.28855(7) 0.0255(3) Uani 1 1 d . . .
H21A H 0.0246 -0.1120 0.2426 0.038 Uiso 1 1 calc R . .
H21B H -0.0163 -0.1722 0.3113 0.038 Uiso 1 1 calc R . .
H21C H 0.1521 -0.1763 0.2921 0.038 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
N1 C1 1.3766(18) . ?
N1 C4 1.3989(18) . ?
N1 C9 1.4673(17) . ?
O1 C12 1.3593(18) . ?
O1 C7 1.4150(17) . ?
O2 C12 1.2007(19) . ?
O3 C20 1.3734(18) . ?
O3 C17 1.4079(17) . ?
O4 C20 1.1915(19) . ?
C1 C5 1.395(2) . ?
C1 C2 1.4153(19) . ?
C2 C8 1.403(2) . ?
C2 C3 1.432(2) . ?
C3 C4 1.3764(19) . ?
C3 C11 1.4980(19) . ?
C4 C14 1.4721(19) . ?
C5 C6 1.384(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.397(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.375(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.520(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.489(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.399(2) . ?
C14 C15 1.4032(19) . ?
C15 C16 1.386(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.383(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.379(2) . ?
C18 C19 1.389(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.495(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 108.00(11) . . ?
C1 N1 C9 122.77(11) . . ?
C4 N1 C9 126.42(12) . . ?
C12 O1 C7 117.30(11) . . ?
C20 O3 C17 116.09(11) . . ?
N1 C1 C5 129.48(13) . . ?
N1 C1 C2 108.23(12) . . ?
C5 C1 C2 122.24(13) . . ?
C8 C2 C1 118.94(13) . . ?
C8 C2 C3 133.71(13) . . ?
C1 C2 C3 107.27(12) . . ?
C4 C3 C2 106.57(12) . . ?
C4 C3 C11 127.56(13) . . ?
C2 C3 C11 125.87(13) . . ?
C3 C4 N1 109.91(12) . . ?
C3 C4 C14 129.31(13) . . ?
N1 C4 C14 120.78(12) . . ?
C6 C5 C1 117.84(13) . . ?
C6 C5 H5A 121.1 . . ?
C1 C5 H5A 121.1 . . ?
C5 C6 C7 119.89(13) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C8 C7 C6 123.15(13) . . ?
C8 C7 O1 118.37(13) . . ?
C6 C7 O1 118.29(13) . . ?
C7 C8 C2 117.93(13) . . ?
C7 C8 H8A 121.0 . . ?
C2 C8 H8A 121.0 . . ?
N1 C9 C10 113.36(12) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O1 123.21(13) . . ?
O2 C12 C13 126.33(14) . . ?
O1 C12 C13 110.46(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.53(13) . . ?
C19 C14 C4 120.41(12) . . ?
C15 C14 C4 121.04(12) . . ?
C16 C15 C14 120.97(13) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 118.61(13) . . ?
C15 C16 H16A 120.7 . . ?
C17 C16 H16A 120.7 . . ?
C18 C17 C16 122.13(13) . . ?
C18 C17 O3 118.19(13) . . ?
C16 C17 O3 119.60(12) . . ?
C17 C18 C19 118.82(13) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 120.6 . . ?
C18 C19 C14 120.81(13) . . ?
C18 C19 H19A 119.6 . . ?
C14 C19 H19A 119.6 . . ?
O4 C20 O3 122.99(13) . . ?
O4 C20 C21 126.92(13) . . ?
O3 C20 C21 110.09(12) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C4 N1 C1 C5 -176.09(14) . . . . ?
C9 N1 C1 C5 -14.0(2) . . . . ?
C4 N1 C1 C2 1.25(15) . . . . ?
C9 N1 C1 C2 163.36(12) . . . . ?
N1 C1 C2 C8 -177.88(12) . . . . ?
C5 C1 C2 C8 -0.3(2) . . . . ?
N1 C1 C2 C3 -0.60(15) . . . . ?
C5 C1 C2 C3 176.98(12) . . . . ?
C8 C2 C3 C4 176.41(15) . . . . ?
C1 C2 C3 C4 -0.29(15) . . . . ?
C8 C2 C3 C11 -3.7(2) . . . . ?
C1 C2 C3 C11 179.55(13) . . . . ?
C2 C3 C4 N1 1.08(15) . . . . ?
C11 C3 C4 N1 -178.76(13) . . . . ?
C2 C3 C4 C14 -178.43(13) . . . . ?
C11 C3 C4 C14 1.7(2) . . . . ?
C1 N1 C4 C3 -1.48(15) . . . . ?
C9 N1 C4 C3 -162.74(12) . . . . ?
C1 N1 C4 C14 178.08(12) . . . . ?
C9 N1 C4 C14 16.8(2) . . . . ?
N1 C1 C5 C6 176.79(13) . . . . ?
C2 C1 C5 C6 -0.2(2) . . . . ?
C1 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C5 C6 C7 O1 -175.26(12) . . . . ?
C12 O1 C7 C8 93.35(16) . . . . ?
C12 O1 C7 C6 -91.41(16) . . . . ?
C6 C7 C8 C2 -0.3(2) . . . . ?
O1 C7 C8 C2 174.72(12) . . . . ?
C1 C2 C8 C7 0.5(2) . . . . ?
C3 C2 C8 C7 -175.86(14) . . . . ?
C1 N1 C9 C10 84.23(16) . . . . ?
C4 N1 C9 C10 -117.06(15) . . . . ?
C7 O1 C12 O2 1.9(2) . . . . ?
C7 O1 C12 C13 -178.38(12) . . . . ?
C3 C4 C14 C19 51.1(2) . . . . ?
N1 C4 C14 C19 -128.35(14) . . . . ?
C3 C4 C14 C15 -130.59(16) . . . . ?
N1 C4 C14 C15 49.95(19) . . . . ?
C19 C14 C15 C16 2.5(2) . . . . ?
C4 C14 C15 C16 -175.83(12) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 -3.2(2) . . . . ?
C15 C16 C17 O3 -179.91(12) . . . . ?
C20 O3 C17 C18 103.53(15) . . . . ?
C20 O3 C17 C16 -79.64(16) . . . . ?
C16 C17 C18 C19 3.3(2) . . . . ?
O3 C17 C18 C19 -179.94(12) . . . . ?
C17 C18 C19 C14 -0.4(2) . . . . ?
C15 C14 C19 C18 -2.4(2) . . . . ?
C4 C14 C19 C18 175.95(13) . . . . ?
C17 O3 C20 O4 -0.7(2) . . . . ?
C17 O3 C20 C21 179.30(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_4q
_database_code_depnum_ccdc_archive 'CCDC 1905951'
loop_
_audit_author_name
_audit_author_address
'Yaping Shang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 3-ethyl-1-methyl-2-phenyl-1H-indole-5-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0634(4)
_cell_length_b                   8.7636(4)
_cell_length_c                   12.0264(6)
_cell_angle_alpha                74.514(2)
_cell_angle_beta                 77.384(2)
_cell_angle_gamma                72.558(2)
_cell_volume                     772.43(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      41.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9855
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            84136
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         43.32
_reflns_number_total             11574
_reflns_number_gt                5959
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1104P)²+0.2173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11574
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.2392
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.43704(12) 0.76070(12) 0.34984(8) 0.01823(16) Uani 1 1 d . . .
O1 O 1.08818(15) 1.08149(14) 0.18311(11) 0.0363(2) Uani 1 1 d . . .
O2 O 1.16444(12) 0.87217(12) 0.09180(9) 0.02645(18) Uani 1 1 d . . .
C1 C 0.57651(14) 0.83029(13) 0.31099(9) 0.01718(17) Uani 1 1 d . . .
C2 C 0.70799(13) 0.72937(12) 0.24332(9) 0.01612(16) Uani 1 1 d . . .
C3 C 0.64226(13) 0.59505(13) 0.24183(9) 0.01633(16) Uani 1 1 d . . .
C4 C 0.47692(13) 0.61756(12) 0.30794(9) 0.01615(16) Uani 1 1 d . . .
C5 C 0.60029(16) 0.97242(14) 0.33101(10) 0.02140(19) Uani 1 1 d . . .
H5A H 0.5111 1.0398 0.3758 0.026 Uiso 1 1 calc R . .
C6 C 0.75925(16) 1.01022(14) 0.28273(11) 0.0221(2) Uani 1 1 d . . .
H6A H 0.7799 1.1047 0.2959 0.026 Uiso 1 1 calc R . .
C7 C 0.89154(14) 0.91212(13) 0.21443(10) 0.01904(18) Uani 1 1 d . . .
C8 C 0.86704(14) 0.77149(13) 0.19487(9) 0.01734(17) Uani 1 1 d . . .
H8A H 0.9565 0.7052 0.1495 0.021 Uiso 1 1 calc R . .
C9 C 0.27594(16) 0.82882(17) 0.42186(12) 0.0271(2) Uani 1 1 d . . .
H9A H 0.2840 0.9298 0.4383 0.041 Uiso 1 1 calc R . .
H9B H 0.2594 0.7494 0.4954 0.041 Uiso 1 1 calc R . .
H9C H 0.1759 0.8532 0.3804 0.041 Uiso 1 1 calc R . .
C10 C 0.73830(15) 0.45757(14) 0.18171(10) 0.02056(19) Uani 1 1 d . . .
H10A H 0.6759 0.3696 0.2092 0.025 Uiso 1 1 calc R . .
H10B H 0.8576 0.4118 0.2038 0.025 Uiso 1 1 calc R . .
C11 C 0.75465(18) 0.50950(19) 0.04864(12) 0.0298(3) Uani 1 1 d . . .
H11A H 0.8186 0.4146 0.0144 0.045 Uiso 1 1 calc R . .
H11B H 0.8188 0.5947 0.0205 0.045 Uiso 1 1 calc R . .
H11C H 0.6370 0.5524 0.0259 0.045 Uiso 1 1 calc R . .
C12 C 1.05493(15) 0.96575(14) 0.16347(11) 0.0223(2) Uani 1 1 d . . .
C13 C 1.32805(17) 0.91571(18) 0.04140(13) 0.0302(3) Uani 1 1 d . . .
H13A H 1.3987 0.8411 -0.0092 0.045 Uiso 1 1 calc R . .
H13B H 1.3929 0.9071 0.1038 0.045 Uiso 1 1 calc R . .
H13C H 1.3037 1.0284 -0.0046 0.045 Uiso 1 1 calc R . .
C14 C 0.35584(13) 0.51142(13) 0.33435(9) 0.01645(16) Uani 1 1 d . . .
C15 C 0.31825(15) 0.46279(14) 0.24267(10) 0.02015(19) Uani 1 1 d . . .
H15A H 0.3667 0.5029 0.1646 0.024 Uiso 1 1 calc R . .
C16 C 0.21115(15) 0.35679(15) 0.26425(11) 0.0224(2) Uani 1 1 d . . .
H16A H 0.1887 0.3229 0.2015 0.027 Uiso 1 1 calc R . .
C17 C 0.13673(15) 0.30026(14) 0.37834(11) 0.02151(19) Uani 1 1 d . . .
H17A H 0.0618 0.2292 0.3933 0.026 Uiso 1 1 calc R . .
C18 C 0.17232(15) 0.34801(14) 0.47024(10) 0.02122(19) Uani 1 1 d . . .
H18A H 0.1217 0.3094 0.5480 0.025 Uiso 1 1 calc R . .
C19 C 0.28185(14) 0.45224(14) 0.44866(9) 0.01926(18) Uani 1 1 d . . .
H19B H 0.3066 0.4834 0.5119 0.023 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
N1 C1 1.3728(13) . ?
N1 C4 1.3986(14) . ?
N1 C9 1.4538(15) . ?
O1 C12 1.2145(15) . ?
O2 C12 1.3439(16) . ?
O2 C13 1.4430(14) . ?
C1 C5 1.4035(15) . ?
C1 C2 1.4191(15) . ?
C2 C8 1.4011(14) . ?
C2 C3 1.4340(13) . ?
C3 C4 1.3826(14) . ?
C3 C10 1.4950(15) . ?
C4 C14 1.4732(14) . ?
C5 C6 1.3843(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4129(17) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3908(14) . ?
C7 C12 1.4822(15) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.5299(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.4005(15) . ?
C14 C15 1.4013(14) . ?
C15 C16 1.3894(15) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3941(17) . ?
C16 H16A 0.9500 . ?
C17 C18 1.3917(17) . ?
C17 H17A 0.9500 . ?
C18 C19 1.3924(15) . ?
C18 H18A 0.9500 . ?
C19 H19B 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 C4 108.65(9) . . ?
C1 N1 C9 124.34(9) . . ?
C4 N1 C9 127.00(9) . . ?
C12 O2 C13 115.37(10) . . ?
N1 C1 C5 130.10(10) . . ?
N1 C1 C2 107.90(9) . . ?
C5 C1 C2 121.99(10) . . ?
C8 C2 C1 119.50(9) . . ?
C8 C2 C3 133.04(10) . . ?
C1 C2 C3 107.45(9) . . ?
C4 C3 C2 106.46(9) . . ?
C4 C3 C10 127.78(9) . . ?
C2 C3 C10 125.75(9) . . ?
C3 C4 N1 109.54(9) . . ?
C3 C4 C14 127.57(9) . . ?
N1 C4 C14 122.89(9) . . ?
C6 C5 C1 117.17(11) . . ?
C6 C5 H5A 121.4 . . ?
C1 C5 H5A 121.4 . . ?
C5 C6 C7 121.80(10) . . ?
C5 C6 H6A 119.1 . . ?
C7 C6 H6A 119.1 . . ?
C8 C7 C6 120.71(10) . . ?
C8 C7 C12 121.56(11) . . ?
C6 C7 C12 117.72(10) . . ?
C7 C8 C2 118.81(10) . . ?
C7 C8 H8A 120.6 . . ?
C2 C8 H8A 120.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 C11 113.29(10) . . ?
C3 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C3 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 O2 122.88(11) . . ?
O1 C12 C7 124.48(12) . . ?
O2 C12 C7 112.63(9) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.68(9) . . ?
C19 C14 C4 122.21(9) . . ?
C15 C14 C4 119.07(9) . . ?
C16 C15 C14 120.94(10) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 119.79(10) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C18 119.90(10) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C19 C18 C17 120.24(10) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C14 120.43(10) . . ?
C18 C19 H19B 119.8 . . ?
C14 C19 H19B 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C5 -178.95(11) . . . . ?
C9 N1 C1 C5 1.47(19) . . . . ?
C4 N1 C1 C2 -0.17(12) . . . . ?
C9 N1 C1 C2 -179.75(11) . . . . ?
N1 C1 C2 C8 -178.73(9) . . . . ?
C5 C1 C2 C8 0.17(16) . . . . ?
N1 C1 C2 C3 0.36(12) . . . . ?
C5 C1 C2 C3 179.25(10) . . . . ?
C8 C2 C3 C4 178.50(11) . . . . ?
C1 C2 C3 C4 -0.41(11) . . . . ?
C8 C2 C3 C10 -0.41(19) . . . . ?
C1 C2 C3 C10 -179.32(10) . . . . ?
C2 C3 C4 N1 0.31(12) . . . . ?
C10 C3 C4 N1 179.19(10) . . . . ?
C2 C3 C4 C14 -179.16(10) . . . . ?
C10 C3 C4 C14 -0.28(18) . . . . ?
C1 N1 C4 C3 -0.09(12) . . . . ?
C9 N1 C4 C3 179.47(11) . . . . ?
C1 N1 C4 C14 179.41(9) . . . . ?
C9 N1 C4 C14 -1.03(17) . . . . ?
N1 C1 C5 C6 178.01(11) . . . . ?
C2 C1 C5 C6 -0.62(17) . . . . ?
C1 C5 C6 C7 1.04(17) . . . . ?
C5 C6 C7 C8 -1.03(18) . . . . ?
C5 C6 C7 C12 178.11(11) . . . . ?
C6 C7 C8 C2 0.54(16) . . . . ?
C12 C7 C8 C2 -178.57(10) . . . . ?
C1 C2 C8 C7 -0.12(15) . . . . ?
C3 C2 C8 C7 -178.92(11) . . . . ?
C4 C3 C10 C11 109.75(13) . . . . ?
C2 C3 C10 C11 -71.58(14) . . . . ?
C13 O2 C12 O1 1.58(18) . . . . ?
C13 O2 C12 C7 -178.60(10) . . . . ?
C8 C7 C12 O1 -175.36(12) . . . . ?
C6 C7 C12 O1 5.51(19) . . . . ?
C8 C7 C12 O2 4.83(16) . . . . ?
C6 C7 C12 O2 -174.30(10) . . . . ?
C3 C4 C14 C19 127.31(12) . . . . ?
N1 C4 C14 C19 -52.09(15) . . . . ?
C3 C4 C14 C15 -50.25(16) . . . . ?
N1 C4 C14 C15 130.35(11) . . . . ?
C19 C14 C15 C16 -0.60(17) . . . . ?
C4 C14 C15 C16 177.05(10) . . . . ?
C14 C15 C16 C17 1.33(18) . . . . ?
C15 C16 C17 C18 -1.06(18) . . . . ?
C16 C17 C18 C19 0.08(18) . . . . ?
C17 C18 C19 C14 0.66(17) . . . . ?
C15 C14 C19 C18 -0.40(16) . . . . ?
C4 C14 C19 C18 -177.97(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        43.32
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.077
