#------------------------------------------------------------------------------
#$Date: 2020-07-06 04:52:47 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126457.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_7126457
loop_
_publ_author_name
'Zeng, Hao'
'Zhu, Chuanle'
'Liu, Chi'
'Cai, Yingying'
'Chen, Fulin'
'Jiang, Huanfeng'
_publ_section_title
;
 Three component hydroxyletherification and hydroxylazidation of
 (trifluoromethyl)alkenes: access to α-trifluoromethyl β-heteroatom
 substituted tertiary alcohols.
;
_journal_issue                   46
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6241
_journal_page_last               6244
_journal_paper_doi               10.1039/d0cc02550j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C15 H14 F3 N O2 S'
_chemical_formula_sum            'C15 H14 F3 N O2 S'
_chemical_formula_weight         329.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-27 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.176(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.516(3)
_cell_length_b                   5.6738(5)
_cell_length_c                   21.937(2)
_cell_measurement_reflns_used    1197
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.012
_cell_measurement_theta_min      3.022
_cell_volume                     2981.0(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10820
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0944 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.8634. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0268P)²+7.0399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1630
_reflns_number_total             2829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc02550j2.cif
_cod_data_source_block           zz
_cod_depositor_comments          'Adding full bibliography for 7126457.cif.'
_cod_database_code               7126457
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C12(H12), C15(H15), C14(H14), C3(H3), C2(H2A), C1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.39458(5) 0.87249(19) 0.22976(5) 0.0274(3) Uani 1 d . . .
F1 F 0.29397(10) 0.6903(4) 0.39969(10) 0.0344(6) Uani 1 d . . .
O1 O 0.36818(12) 0.3907(5) 0.37098(11) 0.0270(7) Uani 1 d . . .
F2 F 0.31596(11) 0.4535(5) 0.48151(12) 0.0523(8) Uani 1 d . . .
F3 F 0.31820(11) 0.8278(5) 0.49629(12) 0.0563(9) Uani 1 d . . .
O2 O 0.39682(13) 0.8742(5) 0.43189(12) 0.0322(8) Uani 1 d . . .
H2 H 0.3883 0.8458 0.3921 0.048 Uiso 1 calc . . GR
N1 N 0.37336(14) 0.5577(6) 0.32543(15) 0.0241(8) Uani 1 d . . .
C5 C 0.33875(17) 0.5115(7) 0.26770(17) 0.0212(9) Uani 1 d . . .
C13 C 0.50300(17) 0.7105(7) 0.66368(18) 0.0217(9) Uani 1 d . . .
H13 H 0.5281 0.7205 0.7072 0.026 Uiso 1 calc . . R
C4 C 0.34135(16) 0.6674(7) 0.21601(17) 0.0200(9) Uani 1 d . . .
C11 C 0.46423(16) 0.8752(7) 0.55664(17) 0.0198(9) Uani 1 d . . .
H11 H 0.4631 0.9988 0.5270 0.024 Uiso 1 calc . . R
C10 C 0.42941(17) 0.6819(7) 0.53574(17) 0.0209(9) Uani 1 d . . .
C12 C 0.50076(16) 0.8905(7) 0.62041(18) 0.0220(9) Uani 1 d . . .
H12 H 0.5242 1.0246 0.6342 0.026 Uiso 1 calc . . R
C8 C 0.39064(17) 0.6648(7) 0.46485(17) 0.0212(9) Uani 1 d . . .
C15 C 0.43173(17) 0.5011(7) 0.57998(17) 0.0228(9) Uani 1 d . . .
H15 H 0.4080 0.3679 0.5665 0.027 Uiso 1 calc . . R
C14 C 0.46866(17) 0.5154(7) 0.64361(18) 0.0226(9) Uani 1 d . . .
H14 H 0.4703 0.3914 0.6733 0.027 Uiso 1 calc . . R
C3 C 0.30497(17) 0.6812(7) 0.15350(18) 0.0259(10) Uani 1 d . . .
H3 H 0.2732 0.5826 0.1366 0.031 Uiso 1 calc . . R
C6 C 0.29720(17) 0.3135(7) 0.25293(18) 0.0271(10) Uani 1 d . . .
H6A H 0.3159 0.1686 0.2737 0.041 Uiso 1 calc . . GR
H6B H 0.2813 0.2901 0.2058 0.041 Uiso 1 calc . . GR
H6C H 0.2673 0.3526 0.2697 0.041 Uiso 1 calc . . GR
C2 C 0.31960(18) 0.8576(8) 0.11662(19) 0.0288(10) Uani 1 d . . .
H2A H 0.2987 0.8904 0.0724 0.035 Uiso 1 calc . . R
C7 C 0.40616(18) 0.4464(7) 0.43418(17) 0.0258(10) Uani 1 d . . .
H7A H 0.4437 0.4703 0.4315 0.031 Uiso 1 calc . . R
H7B H 0.4084 0.3100 0.4631 0.031 Uiso 1 calc . . R
C9 C 0.32986(19) 0.6608(8) 0.4603(2) 0.0340(11) Uani 1 d . . .
C1 C 0.36678(18) 0.9745(7) 0.15130(19) 0.0279(10) Uani 1 d . . .
H1 H 0.3827 1.0984 0.1343 0.033 Uiso 1 calc . . R
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
C1 S1 C4 91.4(2) . . ?
N1 O1 C7 109.9(3) . . ?
C8 O2 H2 109.5 . . ?
C5 N1 O1 110.9(3) . . ?
N1 C5 C4 116.0(4) . . ?
N1 C5 C6 123.7(3) . . ?
C4 C5 C6 120.3(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C5 C4 S1 121.0(3) . . ?
C3 C4 S1 110.9(3) . . ?
C3 C4 C5 128.1(4) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C10 C8 120.1(3) . . ?
C11 C10 C15 118.8(4) . . ?
C15 C10 C8 121.1(3) . . ?
C13 C12 C11 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
O2 C8 C10 108.4(3) . . ?
O2 C8 C7 111.2(3) . . ?
O2 C8 C9 105.5(3) . . ?
C7 C8 C10 108.9(3) . . ?
C9 C8 C10 110.8(3) . . ?
C9 C8 C7 111.9(3) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C4 C3 H3 123.5 . . ?
C4 C3 C2 113.1(4) . . ?
C2 C3 H3 123.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C2 H2A 123.7 . . ?
C1 C2 C3 112.5(4) . . ?
C1 C2 H2A 123.7 . . ?
O1 C7 C8 114.6(3) . . ?
O1 C7 H7A 108.6 . . ?
O1 C7 H7B 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
F1 C9 F2 106.2(4) . . ?
F1 C9 C8 113.4(3) . . ?
F2 C9 C8 111.9(4) . . ?
F3 C9 F1 106.5(3) . . ?
F3 C9 F2 105.9(3) . . ?
F3 C9 C8 112.4(4) . . ?
S1 C1 H1 123.9 . . ?
C2 C1 S1 112.2(3) . . ?
C2 C1 H1 123.9 . . ?
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
S1 C4 1.734(4) . ?
S1 C1 1.720(4) . ?
F1 C9 1.339(5) . ?
O1 N1 1.416(4) . ?
O1 C7 1.426(4) . ?
F2 C9 1.356(5) . ?
F3 C9 1.332(5) . ?
O2 H2 0.8400 . ?
O2 C8 1.427(4) . ?
N1 C5 1.297(5) . ?
C5 C4 1.458(5) . ?
C5 C6 1.501(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(5) . ?
C13 C14 1.386(5) . ?
C4 C3 1.367(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(5) . ?
C11 C12 1.391(5) . ?
C10 C8 1.531(5) . ?
C10 C15 1.399(5) . ?
C12 H12 0.9500 . ?
C8 C7 1.526(5) . ?
C8 C9 1.519(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(5) . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.415(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C2 H2A 0.9500 . ?
C2 C1 1.355(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 H1 0.9500 . ?
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
O2 H2 N1 0.84 2.14 2.841(4) 141.2 .
