#------------------------------------------------------------------------------
#$Date: 2021-09-03 22:29:40 +0300 (Fri, 03 Sep 2021) $
#$Revision: 268393 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518958.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_4518958
loop_
_publ_author_name
'Guo, Hongyu'
'Zhang, Sheng'
'Yu, Xiaoqiang'
'Feng, Xiujuan'
'Yamamoto, Yoshinori'
'Bao, Ming'
_publ_section_title
;
 [3 + 2] Cycloaddition of α-Aryl-α-diazoacetates with Terminal Alkynes
 via the Cooperative Catalysis of Palladium and Acid
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10789
_journal_page_last               10795
_journal_paper_doi               10.1021/acscatal.1c02533
_journal_year                    2021
_chemical_formula_moiety         'C18 H13 F3 O2'
_chemical_formula_sum            'C18 H13 F3 O2'
_chemical_formula_weight         318.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-16
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 101.044(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.918(4)
_cell_length_b                   5.5061(8)
_cell_length_c                   10.7277(15)
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.892
_cell_measurement_theta_min      2.263
_cell_volume                     1502.6(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker SMART'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7052
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.738
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0946 before and 0.0538 after correction. 
The Ratio of minimum to maximum transmission is 0.8923. 
The λ/2 correction factor is Not present. 
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
; 
 Flack x determined using 662 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0597
_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)+(0.0490P)²+0.9897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                2153
_reflns_number_total             3238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c02533_si_002.cif
_cod_data_source_block           zhl
_cod_original_cell_volume        1502.5(4)
_cod_database_code               4518958
_shelx_shelxl_version_number     2016/6
_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   0.977
_shelx_estimated_absorpt_t_min   0.977
_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: 
 C008(H008), C009(H009), C00B(H00B), C00E(H00E), C00G(H00G), C00H(H00H), 
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M) 
2.b Idealised Me refined as rotating group: 
 C00L(H00A,H00C,H00D) 
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
O001 O 0.60023(11) 0.3106(6) 0.3167(3) 0.0323(8) Uani 1 1 d . . . . .
O002 O 0.53845(12) 0.3214(7) 0.1320(3) 0.0408(9) Uani 1 1 d . . . . .
F003 F 0.83067(12) 0.2457(8) 0.7965(4) 0.0885(15) Uani 1 1 d . . . . .
F004 F 0.79680(14) -0.0897(8) 0.8107(4) 0.0939(15) Uani 1 1 d . . . . .
F005 F 0.77967(15) 0.1931(12) 0.9247(3) 0.130(2) Uani 1 1 d . . . . .
C006 C 0.55642(17) 0.4126(9) 0.2475(4) 0.0311(11) Uani 1 1 d . . . . .
C007 C 0.48916(17) 0.7390(8) 0.2695(4) 0.0305(11) Uani 1 1 d . . . . .
C008 C 0.44772(17) 0.6570(10) 0.1751(4) 0.0370(12) Uani 1 1 d . . . . .
H008 H 0.451587 0.510771 0.130847 0.044 Uiso 1 1 calc R . . . .
C009 C 0.48232(19) 0.9599(9) 0.3286(4) 0.0356(12) Uani 1 1 d . . . . .
H009 H 0.510276 1.022744 0.390629 0.043 Uiso 1 1 calc R . . . .
C00A C 0.65553(16) 0.3633(10) 0.5248(4) 0.0315(11) Uani 1 1 d . . . . .
C00B C 0.57335(17) 0.6136(10) 0.4282(4) 0.0325(11) Uani 1 1 d . . . . .
H00B H 0.571467 0.727428 0.493685 0.039 Uiso 1 1 calc R . . . .
C00C C 0.61049(17) 0.4409(9) 0.4315(4) 0.0327(11) Uani 1 1 d . . . . .
C00D C 0.74043(17) 0.2210(10) 0.7109(4) 0.0376(13) Uani 1 1 d . . . . .
C00E C 0.43587(18) 1.0885(10) 0.2990(4) 0.0389(12) Uani 1 1 d . . . . .
H00E H 0.432003 1.237091 0.341351 0.047 Uiso 1 1 calc R . . . .
C00F C 0.53721(17) 0.5968(9) 0.3093(4) 0.0310(11) Uani 1 1 d . . . . .
C00G C 0.3948(2) 1.0013(11) 0.2075(5) 0.0445(14) Uani 1 1 d . . . . .
H00G H 0.362634 1.088398 0.187702 0.053 Uiso 1 1 calc R . . . .
C00H C 0.67091(18) 0.5011(9) 0.6348(4) 0.0351(12) Uani 1 1 d . . . . .
H00H H 0.652197 0.644850 0.646874 0.042 Uiso 1 1 calc R . . . .
C00I C 0.40114(18) 0.7870(10) 0.1458(5) 0.0408(13) Uani 1 1 d . . . . .
H00I H 0.373281 0.727733 0.082339 0.049 Uiso 1 1 calc R . . . .
C00J C 0.72560(17) 0.0790(10) 0.6029(4) 0.0382(12) Uani 1 1 d . . . . .
H00J H 0.744207 -0.066213 0.593000 0.046 Uiso 1 1 calc R . . . .
C00K C 0.71317(19) 0.4296(11) 0.7261(5) 0.0409(13) Uani 1 1 d . . . . .
H00K H 0.723545 0.525565 0.800243 0.049 Uiso 1 1 calc R . . . .
C00L C 0.56811(18) 0.1298(10) 0.0886(4) 0.0399(13) Uani 1 1 d . . . . .
H00A H 0.552635 0.089762 0.000355 0.060 Uiso 1 1 calc GR . . . .
H00C H 0.567395 -0.014062 0.142054 0.060 Uiso 1 1 calc GR . . . .
H00D H 0.604558 0.182746 0.093796 0.060 Uiso 1 1 calc GR . . . .
C00M C 0.68341(17) 0.1501(10) 0.5094(4) 0.0356(11) Uani 1 1 d . . . . .
H00M H 0.673442 0.054409 0.434980 0.043 Uiso 1 1 calc R . . . .
C00N C 0.7858(2) 0.1444(12) 0.8106(5) 0.0491(14) 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 0.0033 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'
O O 0.0106 0.0060 '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
C006 O001 C00C 105.5(3) . . ?
C006 O002 C00L 117.7(3) . . ?
O001 C006 C00F 113.0(4) . . ?
O002 C006 O001 117.4(4) . . ?
O002 C006 C00F 129.7(4) . . ?
C008 C007 C00F 122.0(4) . . ?
C009 C007 C008 117.5(4) . . ?
C009 C007 C00F 120.5(4) . . ?
C007 C008 H008 119.6 . . ?
C00I C008 C007 120.7(5) . . ?
C00I C008 H008 119.6 . . ?
C007 C009 H009 119.2 . . ?
C00E C009 C007 121.5(5) . . ?
C00E C009 H009 119.2 . . ?
C00H C00A C00C 119.1(4) . . ?
C00H C00A C00M 118.9(4) . . ?
C00M C00A C00C 122.0(4) . . ?
C00C C00B H00B 125.7 . . ?
C00C C00B C00F 108.6(4) . . ?
C00F C00B H00B 125.7 . . ?
O001 C00C C00A 116.5(4) . . ?
C00B C00C O001 108.8(4) . . ?
C00B C00C C00A 134.6(4) . . ?
C00J C00D C00N 119.5(5) . . ?
C00K C00D C00J 120.2(4) . . ?
C00K C00D C00N 120.3(5) . . ?
C009 C00E H00E 119.9 . . ?
C009 C00E C00G 120.1(5) . . ?
C00G C00E H00E 119.9 . . ?
C006 C00F C007 128.9(4) . . ?
C006 C00F C00B 104.1(4) . . ?
C00B C00F C007 126.9(4) . . ?
C00E C00G H00G 120.3 . . ?
C00I C00G C00E 119.4(5) . . ?
C00I C00G H00G 120.3 . . ?
C00A C00H H00H 119.8 . . ?
C00K C00H C00A 120.3(5) . . ?
C00K C00H H00H 119.8 . . ?
C008 C00I H00I 119.6 . . ?
C00G C00I C008 120.7(5) . . ?
C00G C00I H00I 119.6 . . ?
C00D C00J H00J 120.1 . . ?
C00D C00J C00M 119.8(5) . . ?
C00M C00J H00J 120.1 . . ?
C00D C00K C00H 120.7(5) . . ?
C00D C00K H00K 119.6 . . ?
C00H C00K H00K 119.6 . . ?
O002 C00L H00A 109.5 . . ?
O002 C00L H00C 109.5 . . ?
O002 C00L H00D 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00A C00L H00D 109.5 . . ?
H00C C00L H00D 109.5 . . ?
C00A C00M H00M 120.0 . . ?
C00J C00M C00A 120.1(4) . . ?
C00J C00M H00M 120.0 . . ?
F003 C00N C00D 112.8(5) . . ?
F004 C00N F003 102.5(5) . . ?
F004 C00N C00D 114.7(5) . . ?
F005 C00N F003 106.9(5) . . ?
F005 C00N F004 105.5(6) . . ?
F005 C00N C00D 113.5(5) . . ?
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
O001 C006 1.353(5) . ?
O001 C00C 1.406(5) . ?
O002 C006 1.336(5) . ?
O002 C00L 1.435(6) . ?
F003 C00N 1.325(6) . ?
F004 C00N 1.320(7) . ?
F005 C00N 1.292(6) . ?
C006 C00F 1.358(7) . ?
C007 C008 1.402(6) . ?
C007 C009 1.399(6) . ?
C007 C00F 1.463(6) . ?
C008 H008 0.9500 . ?
C008 C00I 1.387(6) . ?
C009 H009 0.9500 . ?
C009 C00E 1.381(6) . ?
C00A C00C 1.449(6) . ?
C00A C00H 1.396(6) . ?
C00A C00M 1.404(7) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.349(6) . ?
C00B C00F 1.433(6) . ?
C00D C00J 1.390(7) . ?
C00D C00K 1.374(7) . ?
C00D C00N 1.490(6) . ?
C00E H00E 0.9500 . ?
C00E C00G 1.388(7) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.378(7) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.379(6) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00M 1.391(6) . ?
C00K H00K 0.9500 . ?
C00L H00A 0.9800 . ?
C00L H00C 0.9800 . ?
C00L H00D 0.9800 . ?
C00M H00M 0.9500 . ?
