#------------------------------------------------------------------------------
#$Date: 2019-11-11 19:05:48 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/55/4035549.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_4035549
loop_
_publ_author_name
'Chen, Long'
'Wu, Lianlian'
'Duan, Weijie'
'Wang, Tao'
'Li, Letian'
'Zhang, Keke'
'Zhu, Jingmei'
'Peng, Zhi'
'Xiong, Fei'
_publ_section_title
;
 Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates
 with CF₃SO₂Cl To Construct 3-Trifluoromethyl
 Coumarin Derivatives.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8607
_journal_page_last               8614
_journal_paper_doi               10.1021/acs.joc.8b00581
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H11 F3 O2'
_chemical_formula_sum            'C17 H11 F3 O2'
_chemical_formula_weight         304.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.308(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4148(5)
_cell_length_b                   7.9614(4)
_cell_length_c                   14.3307(6)
_cell_measurement_reflns_used    5482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3840
_cell_measurement_theta_min      4.1000
_cell_volume                     1414.07(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -35.00  53.00   1.00    3.95    --  -15.92  37.00 150.00   88
  2  ω    -88.00 -35.00   1.00    3.95    --  -15.92-178.00 120.00   53
  3  ω    -45.00  55.00   1.00    3.95    --  -15.92  19.00  90.00  100
  4  ω    -52.00  36.00   1.00    3.95    --   16.85 -37.00-120.00   88
  5  ω      0.00  84.00   1.00    3.95    --   16.85  57.00-180.00   84
  6  ω    -20.00   5.00   1.00    3.95    --   16.85 -99.00  30.00   25
  7  ω    -10.00  84.00   1.00    3.95    --   16.85  77.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0247802000
_diffrn_orient_matrix_UB_12      -0.0532202000
_diffrn_orient_matrix_UB_13      -0.0321656000
_diffrn_orient_matrix_UB_21      0.0373823000
_diffrn_orient_matrix_UB_22      -0.0274290000
_diffrn_orient_matrix_UB_23      0.0360919000
_diffrn_orient_matrix_UB_31      -0.0355541000
_diffrn_orient_matrix_UB_32      -0.0659918000
_diffrn_orient_matrix_UB_33      0.0109375000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16163
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.397
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0736
_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)+(0.0520P)²+0.4100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             3502
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00581_si_002.cif
_cod_data_source_block           cl20170310
_cod_original_cell_volume        1414.08(11)
_cod_database_code               4035549
_shelxl_version_number           2014-1
_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.
;
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.535
_oxdiff_exptl_absorpt_empirical_full_min 0.542
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'
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
F1 F 0.14529(10) 0.1416(2) -0.08035(10) 0.0900(5) Uani 1 1 d .
F2 F 0.20542(11) -0.06040(16) 0.00378(11) 0.0874(4) Uani 1 1 d .
F3 F 0.11521(10) 0.1311(2) 0.06353(11) 0.0989(5) Uani 1 1 d .
O1 O 0.48226(9) 0.20496(17) -0.00624(8) 0.0511(3) Uani 1 1 d .
O2 O 0.37236(11) 0.0575(2) -0.09921(9) 0.0652(4) Uani 1 1 d .
C1 C 0.38170(14) 0.1460(2) -0.03125(11) 0.0475(4) Uani 1 1 d .
C2 C 0.29331(13) 0.1980(2) 0.02580(11) 0.0442(4) Uani 1 1 d .
C3 C 0.30810(12) 0.3179(2) 0.09259(10) 0.0399(4) Uani 1 1 d .
C4 C 0.41634(12) 0.3775(2) 0.11594(10) 0.0406(4) Uani 1 1 d .
C5 C 0.44350(14) 0.4911(2) 0.18814(12) 0.0496(4) Uani 1 1 d .
H5 H 0.3891 0.5386 0.2215 0.060 Uiso 1 1 calc R
C6 C 0.54866(15) 0.5332(3) 0.21046(13) 0.0558(5) Uani 1 1 d .
H6 H 0.5645 0.6086 0.2589 0.067 Uiso 1 1 calc R
C7 C 0.63238(14) 0.4653(2) 0.16213(12) 0.0515(4) Uani 1 1 d .
C8 C 0.60726(13) 0.3558(2) 0.08973(12) 0.0505(4) Uani 1 1 d .
H8 H 0.6619 0.3100 0.0560 0.061 Uiso 1 1 calc R
C9 C 0.50106(13) 0.3139(2) 0.06723(10) 0.0420(4) Uani 1 1 d .
C10 C 0.21736(12) 0.3946(2) 0.14211(11) 0.0434(4) Uani 1 1 d .
C11 C 0.14869(15) 0.5055(3) 0.09465(14) 0.0592(5) Uani 1 1 d .
H11 H 0.1593 0.5322 0.0327 0.071 Uiso 1 1 calc R
C12 C 0.06422(16) 0.5768(3) 0.13901(17) 0.0724(6) Uani 1 1 d .
H12 H 0.0187 0.6526 0.1070 0.087 Uiso 1 1 calc R
C13 C 0.04700(15) 0.5368(3) 0.22990(16) 0.0684(6) Uani 1 1 d .
H13 H -0.0111 0.5832 0.2590 0.082 Uiso 1 1 calc R
C14 C 0.11520(16) 0.4286(3) 0.27764(14) 0.0636(6) Uani 1 1 d .
H14 H 0.1035 0.4019 0.3394 0.076 Uiso 1 1 calc R
C15 C 0.20188(15) 0.3582(2) 0.23494(12) 0.0521(4) Uani 1 1 d .
H15 H 0.2493 0.2870 0.2684 0.063 Uiso 1 1 calc R
C16 C 0.18990(15) 0.1051(3) 0.00349(13) 0.0568(5) Uani 1 1 d .
C17 C 0.74784(16) 0.5090(3) 0.18935(16) 0.0725(6) Uani 1 1 d .
H17A H 0.7619 0.4892 0.2550 0.109 Uiso 1 1 calc GR
H17B H 0.7604 0.6252 0.1758 0.109 Uiso 1 1 calc GR
H17C H 0.7949 0.4403 0.1546 0.109 Uiso 1 1 calc GR
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C9 122.13(13)
O1 C1 C2 117.41(15)
O2 C1 O1 117.33(15)
O2 C1 C2 125.25(17)
C1 C2 C16 113.63(15)
C3 C2 C1 121.14(15)
C3 C2 C16 125.22(15)
C2 C3 C4 118.72(14)
C2 C3 C10 123.16(15)
C4 C3 C10 118.11(14)
C5 C4 C3 124.32(14)
C9 C4 C3 118.93(15)
C9 C4 C5 116.68(15)
C6 C5 C4 121.12(16)
C5 C6 C7 121.26(18)
C6 C7 C17 120.62(18)
C8 C7 C6 118.53(16)
C8 C7 C17 120.84(18)
C7 C8 C9 120.05(16)
O1 C9 C4 120.97(14)
O1 C9 C8 116.70(14)
C8 C9 C4 122.32(16)
C11 C10 C3 119.25(15)
C11 C10 C15 119.43(16)
C15 C10 C3 121.32(15)
C10 C11 C12 120.06(19)
C13 C12 C11 120.5(2)
C14 C13 C12 119.84(18)
C13 C14 C15 120.61(19)
C10 C15 C14 119.54(19)
F1 C16 F2 105.83(16)
F1 C16 C2 113.11(17)
F2 C16 C2 111.44(16)
F3 C16 F1 106.52(17)
F3 C16 F2 105.13(18)
F3 C16 C2 114.14(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C16 1.326(2)
F2 C16 1.331(2)
F3 C16 1.317(2)
O1 C1 1.362(2)
O1 C9 1.374(2)
O2 C1 1.203(2)
C1 C2 1.465(2)
C2 C3 1.356(2)
C2 C16 1.500(3)
C3 C4 1.446(2)
C3 C10 1.496(2)
C4 C5 1.400(2)
C4 C9 1.391(2)
C5 C6 1.368(2)
C6 C7 1.391(3)
C7 C8 1.377(3)
C7 C17 1.504(3)
C8 C9 1.380(2)
C10 C11 1.379(3)
C10 C15 1.386(2)
C11 C12 1.380(3)
C12 C13 1.370(3)
C13 C14 1.364(3)
C14 C15 1.387(3)
