#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:12:09 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240324.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240324
loop_
_publ_author_name
'Shi, Lijun'
'Liu, Ying'
'Wang, Caixia'
'Yuan, Xinxin'
'Liu, Xiaobiao'
'Wu, Lulu'
'Pan, Zhenliang'
'Yu, Qicheng'
'Xu, Cuilian'
'Yang, Guoyu'
_publ_section_title
;
 Synthesis of 1-(β-coumarinyl)-1-(β-indolyl)trifluoroethanols through
 regioselective Friedel--Crafts alkylation of indoles with
 β-(trifluoroacetyl)coumarins catalyzed by Sc(OTf)3
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              13929
_journal_page_last               13935
_journal_paper_doi               10.1039/D0RA01237H
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C19 H12 F3 N O3'
_chemical_formula_sum            'C19 H12 F3 N O3'
_chemical_formula_weight         359.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-08-30 deposited with the CCDC.	2020-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.277(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8958(2)
_cell_length_b                   15.5043(9)
_cell_length_c                   17.1980(6)
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3950
_cell_measurement_theta_min      3.8560
_cell_volume                     1551.51(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00  -77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   55.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -116.0000  -15.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   14.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   75.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega   56.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   -4.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
 14 omega   92.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   55.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00  131.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 18 omega   59.00  124.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  150.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0742962000
_diffrn_orient_matrix_UB_12      0.0474152000
_diffrn_orient_matrix_UB_13      0.0787020000
_diffrn_orient_matrix_UB_21      0.0313810000
_diffrn_orient_matrix_UB_22      -0.0872978000
_diffrn_orient_matrix_UB_23      0.0431840000
_diffrn_orient_matrix_UB_31      0.2521809000
_diffrn_orient_matrix_UB_32      -0.0031237000
_diffrn_orient_matrix_UB_33      -0.0132097000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5737
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.056
_diffrn_reflns_theta_max         67.056
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0522
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1915
_reflns_number_total             2762
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra01237h2.cif
_cod_data_source_block           201709186
_cod_depositor_comments
'Adding full bibliography for 7240324--7240325.cif.'
_cod_original_cell_volume        1551.49(13)
_cod_database_code               7240324
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H41N2O2F3
_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.
;
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), N1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2663(4) 0.30773(17) 0.40498(14) 0.0480(6) Uani 1 1 d . . . . .
C2 C 0.1822(5) 0.39810(19) 0.42195(15) 0.0576(7) Uani 1 1 d . . . . .
C3 C -0.0675(4) 0.29620(19) 0.28706(14) 0.0551(7) Uani 1 1 d . . . . .
H3 H -0.1632 0.3383 0.3026 0.066 Uiso 1 1 calc R . . . .
C4 C 0.1431(4) 0.27368(18) 0.32728(13) 0.0476(6) Uani 1 1 d . . . . .
C5 C 0.2290(4) 0.20600(17) 0.28342(13) 0.0478(6) Uani 1 1 d . . . . .
C6 C 0.0621(4) 0.19169(18) 0.21649(14) 0.0526(6) Uani 1 1 d . . . . .
C7 C 0.0879(5) 0.1300(2) 0.15994(14) 0.0633(8) Uani 1 1 d . . . . .
H7 H -0.0249 0.1214 0.1162 0.076 Uiso 1 1 calc R . . . .
C8 C 0.2851(5) 0.0825(2) 0.17115(17) 0.0694(8) Uani 1 1 d . . . . .
H8 H 0.3064 0.0406 0.1343 0.083 Uiso 1 1 calc R . . . .
C9 C 0.4564(5) 0.0952(2) 0.23665(16) 0.0665(8) Uani 1 1 d . . . . .
H9 H 0.5893 0.0619 0.2424 0.080 Uiso 1 1 calc R . . . .
C10 C 0.4304(4) 0.15630(19) 0.29258(15) 0.0570(7) Uani 1 1 d . . . . .
H10 H 0.5449 0.1645 0.3359 0.068 Uiso 1 1 calc R . . . .
C11 C 0.4128(4) 0.24385(19) 0.54326(14) 0.0520(6) Uani 1 1 d . . . . .
C12 C 0.2350(4) 0.24653(17) 0.47302(13) 0.0461(6) Uani 1 1 d . . . . .
C13 C 0.0498(4) 0.19573(18) 0.46989(14) 0.0510(6) Uani 1 1 d . . . . .
H13 H -0.0631 0.1977 0.4254 0.061 Uiso 1 1 calc R . . . .
C14 C 0.0200(4) 0.13833(18) 0.53304(14) 0.0524(6) Uani 1 1 d . . . . .
C15 C 0.1900(5) 0.13651(18) 0.59831(14) 0.0554(6) Uani 1 1 d . . . . .
C16 C 0.1777(6) 0.0823(2) 0.66165(16) 0.0709(8) Uani 1 1 d . . . . .
H16 H 0.2949 0.0816 0.7049 0.085 Uiso 1 1 calc R . . . .
C17 C -0.0102(6) 0.0298(2) 0.65930(18) 0.0781(9) Uani 1 1 d . . . . .
H17 H -0.0207 -0.0066 0.7015 0.094 Uiso 1 1 calc R . . . .
C18 C -0.1848(6) 0.0303(2) 0.5949(2) 0.0769(9) Uani 1 1 d . . . . .
H18 H -0.3115 -0.0057 0.5941 0.092 Uiso 1 1 calc R . . . .
C19 C -0.1703(5) 0.0842(2) 0.53206(17) 0.0678(8) Uani 1 1 d . . . . .
H19 H -0.2876 0.0845 0.4888 0.081 Uiso 1 1 calc R . . . .
F1 F 0.1961(3) 0.45280(12) 0.36309(10) 0.0804(6) Uani 1 1 d . . . . .
F2 F -0.0368(3) 0.39840(12) 0.43408(10) 0.0737(5) Uani 1 1 d . . . . .
F3 F 0.3068(3) 0.43228(12) 0.48634(10) 0.0764(5) Uani 1 1 d . . . . .
N1 N -0.1157(3) 0.24735(17) 0.22067(12) 0.0589(6) Uani 1 1 d . . . . .
H1 H -0.2392 0.2509 0.1865 0.071 Uiso 1 1 calc R . . . .
O1 O 0.5026(3) 0.31656(15) 0.39718(10) 0.0617(6) Uani 1 1 d . . . . .
H1A H 0.5805 0.3217 0.4410 0.093 Uiso 1 1 calc GR . . . .
O2 O 0.5890(3) 0.28516(14) 0.55392(11) 0.0656(6) Uani 1 1 d . . . . .
O3 O 0.3812(3) 0.18831(13) 0.60231(10) 0.0589(5) Uani 1 1 d . . . . .
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 C12 109.7(2) . . ?
C4 C1 C2 111.4(2) . . ?
C4 C1 C12 111.0(2) . . ?
O1 C1 C2 106.3(2) . . ?
O1 C1 C4 106.73(19) . . ?
O1 C1 C12 111.62(19) . . ?
F1 C2 C1 112.1(2) . . ?
F1 C2 F2 107.1(2) . . ?
F1 C2 F3 106.5(2) . . ?
F2 C2 C1 112.5(2) . . ?
F3 C2 C1 111.7(2) . . ?
F3 C2 F2 106.5(2) . . ?
C4 C3 H3 125.3 . . ?
N1 C3 H3 125.3 . . ?
N1 C3 C4 109.4(2) . . ?
C3 C4 C1 128.8(2) . . ?
C3 C4 C5 106.9(2) . . ?
C5 C4 C1 124.2(2) . . ?
C6 C5 C4 106.7(2) . . ?
C10 C5 C4 135.1(2) . . ?
C10 C5 C6 118.2(2) . . ?
C7 C6 C5 122.7(3) . . ?
N1 C6 C5 107.4(2) . . ?
N1 C6 C7 129.9(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 120.4 . . ?
C9 C10 C5 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
O2 C11 C12 126.3(3) . . ?
O2 C11 O3 115.9(2) . . ?
O3 C11 C12 117.7(2) . . ?
C11 C12 C1 119.1(2) . . ?
C13 C12 C1 121.9(2) . . ?
C13 C12 C11 119.1(2) . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.1(2) . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C19 118.3(3) . . ?
C19 C14 C13 123.9(2) . . ?
C14 C15 C16 121.9(3) . . ?
O3 C15 C14 120.7(2) . . ?
O3 C15 C16 117.4(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C3 N1 C6 109.7(2) . . ?
C3 N1 H1 125.2 . . ?
C6 N1 H1 125.2 . . ?
C1 O1 H1A 109.5 . . ?
C11 O3 C15 122.59(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.530(4) . ?
C1 C4 1.510(3) . ?
C1 C12 1.541(3) . ?
C1 O1 1.428(3) . ?
C2 F1 1.333(3) . ?
C2 F2 1.340(3) . ?
C2 F3 1.336(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C3 N1 1.361(3) . ?
C4 C5 1.432(4) . ?
C5 C6 1.406(3) . ?
C5 C10 1.403(4) . ?
C6 C7 1.390(4) . ?
C6 N1 1.369(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.467(3) . ?
C11 O2 1.209(3) . ?
C11 O3 1.367(3) . ?
C12 C13 1.341(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.437(3) . ?
C14 C15 1.379(3) . ?
C14 C19 1.399(4) . ?
C15 C16 1.387(4) . ?
C15 O3 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9300 . ?
N1 H1 0.8600 . ?
O1 H1A 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.41 3.146(3) 144.3 4_465
N1 H1 O3 0.86 2.64 3.462(3) 161.5 4_465
O1 H1A O2 0.82 2.02 2.705(3) 141.3 .
