#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:55:35 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253738 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038498.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_4038498
loop_
_publ_author_name
'Zhu, Lifan'
'Guo, Hongyu'
'Feng, Xiujuan'
'Yamamoto, Yoshinori'
'Bao, Ming'
_publ_section_title
;
 Copper-Catalyzed One-Pot Synthesis of 1,3-Enynes from
 2-Chloro-N-(quinolin-8-yl)acetamides and Terminal Alkynes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8740
_journal_page_last               8748
_journal_paper_doi               10.1021/acs.joc.0c01102
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C29 H18 F6 N2 O'
_chemical_formula_sum            'C29 H18 F6 N2 O'
_chemical_formula_weight         524.45
_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     dual
_audit_creation_date             2019-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.769(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5939(6)
_cell_length_b                   13.7390(6)
_cell_length_c                   10.8510(4)
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.52
_cell_measurement_theta_min      2.41
_cell_volume                     2437.98(17)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_reduction        'SAINT V8.32B (?, 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      273.15
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.960
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12577
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.936
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0391 after correction.
The Ratio of minimum to maximum transmission is 0.8817.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0667
_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)+(0.0985P)²+0.5709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2820
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01102_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4038498.cif.'
_cod_database_code               4038498
_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   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N001(H001), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012)
;
_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
N001 N 0.40580(13) 0.39614(17) 0.2458(2) 0.0551(6) Uani 1 1 d . . . . .
H001 H 0.380579 0.364526 0.296167 0.066 Uiso 1 1 calc R . . . .
F002 F 0.12660(14) 0.33212(19) 0.9177(2) 0.1108(9) Uani 1 1 d . . . . .
O003 O 0.52838(13) 0.4080(2) 0.1821(2) 0.0868(8) Uani 1 1 d . . . . .
F004 F 0.09841(14) 0.46286(19) 0.8248(3) 0.1199(9) Uani 1 1 d . . . . .
N005 N 0.24733(14) 0.40558(18) 0.2620(2) 0.0614(7) Uani 1 1 d . . . . .
F006 F 0.92931(14) 0.3268(2) 0.2834(3) 0.1280(11) Uani 1 1 d . . . . .
F007 F 0.96995(15) 0.2644(2) 0.4609(3) 0.1406(12) Uani 1 1 d . . . . .
F008 F 0.05534(14) 0.3310(3) 0.7380(3) 0.1463(13) Uani 1 1 d . . . . .
F009 F 0.97793(14) 0.4126(2) 0.4340(3) 0.1433(12) Uani 1 1 d . . . . .
C00A C 0.27451(16) 0.4678(2) 0.1800(3) 0.0507(7) Uani 1 1 d . . . . .
C00B C 0.35895(16) 0.4647(2) 0.1695(3) 0.0514(7) Uani 1 1 d . . . . .
C00C C 0.69127(16) 0.3668(2) 0.5005(3) 0.0516(7) Uani 1 1 d . . . . .
C00D C 0.48582(17) 0.3730(2) 0.2509(3) 0.0573(7) Uani 1 1 d . . . . .
C00E C 0.51919(16) 0.2993(2) 0.3515(3) 0.0552(7) Uani 1 1 d . . . . .
H00A H 0.479626 0.247355 0.351588 0.066 Uiso 1 1 calc R . . . .
H00B H 0.568900 0.270913 0.331404 0.066 Uiso 1 1 calc R . . . .
C00F C 0.19493(16) 0.3643(2) 0.7501(3) 0.0537(7) Uani 1 1 d . . . . .
C00G C 0.53749(16) 0.3439(2) 0.4806(3) 0.0521(7) Uani 1 1 d . . . . .
C00H C 0.33676(16) 0.3579(2) 0.6477(3) 0.0555(7) Uani 1 1 d . . . . .
C00I C 0.26863(17) 0.3893(2) 0.8209(3) 0.0586(8) Uani 1 1 d . . . . .
H00I H 0.270813 0.408009 0.903758 0.070 Uiso 1 1 calc R . . . .
C00J C 0.22241(18) 0.5352(2) 0.1072(3) 0.0564(7) Uani 1 1 d . . . . .
C00K C 0.84671(16) 0.3512(2) 0.4375(3) 0.0563(7) Uani 1 1 d . . . . .
C00L C 0.46839(17) 0.3518(2) 0.5435(3) 0.0582(8) Uani 1 1 d . . . . .
C00M C 0.33915(17) 0.3871(2) 0.7706(3) 0.0579(8) Uani 1 1 d . . . . .
H00M H 0.388599 0.405104 0.819060 0.070 Uiso 1 1 calc R . . . .
C00N C 0.38865(18) 0.5271(2) 0.0892(3) 0.0595(8) Uani 1 1 d . . . . .
H00N H 0.443530 0.524577 0.081212 0.071 Uiso 1 1 calc R . . . .
C00O C 0.70302(17) 0.3793(2) 0.3779(3) 0.0613(8) Uani 1 1 d . . . . .
H00O H 0.658542 0.393393 0.315961 0.074 Uiso 1 1 calc R . . . .
C00P C 0.61132(17) 0.3711(2) 0.5412(3) 0.0576(7) Uani 1 1 d . . . . .
H00P H 0.611974 0.396542 0.620786 0.069 Uiso 1 1 calc R . . . .
C00Q C 0.40885(18) 0.3547(2) 0.5914(3) 0.0609(8) Uani 1 1 d . . . . .
C00R C 0.76013(18) 0.3501(2) 0.5913(3) 0.0617(8) Uani 1 1 d . . . . .
H00R H 0.754161 0.344143 0.674653 0.074 Uiso 1 1 calc R . . . .
C00S C 0.77992(17) 0.3711(2) 0.3468(3) 0.0641(8) Uani 1 1 d . . . . .
H00S H 0.786807 0.379104 0.264145 0.077 Uiso 1 1 calc R . . . .
C00T C 0.3363(2) 0.5947(2) 0.0192(3) 0.0685(9) Uani 1 1 d . . . . .
H00T H 0.357314 0.637002 -0.034344 0.082 Uiso 1 1 calc R . . . .
C00U C 0.13922(19) 0.5340(3) 0.1200(3) 0.0693(9) Uani 1 1 d . . . . .
H00U H 0.102542 0.576350 0.072902 0.083 Uiso 1 1 calc R . . . .
C00V C 0.83687(18) 0.3423(2) 0.5596(3) 0.0635(8) Uani 1 1 d . . . . .
H00V H 0.882039 0.330868 0.621322 0.076 Uiso 1 1 calc R . . . .
C00W C 0.2555(2) 0.5996(2) 0.0278(3) 0.0678(9) Uani 1 1 d . . . . .
H00W H 0.222111 0.645579 -0.018623 0.081 Uiso 1 1 calc R . . . .
C00X C 0.1186(2) 0.3703(3) 0.8048(3) 0.0704(9) Uani 1 1 d . . . . .
C00Y C 0.26227(19) 0.3310(3) 0.5777(3) 0.0755(10) Uani 1 1 d . . . . .
H00Y H 0.259937 0.310314 0.495548 0.091 Uiso 1 1 calc R . . . .
C00Z C 0.16927(19) 0.4095(3) 0.2697(3) 0.0743(10) Uani 1 1 d . . . . .
H00Z H 0.150296 0.367702 0.325745 0.089 Uiso 1 1 calc R . . . .
C010 C 0.1128(2) 0.4717(3) 0.2001(4) 0.0780(10) Uani 1 1 d . . . . .
H010 H 0.058047 0.470166 0.208762 0.094 Uiso 1 1 calc R . . . .
C011 C 0.92950(19) 0.3399(3) 0.4034(4) 0.0737(10) Uani 1 1 d . . . . .
C012 C 0.19172(19) 0.3345(3) 0.6286(3) 0.0747(10) Uani 1 1 d . . . . .
H012 H 0.141986 0.316797 0.580654 0.090 Uiso 1 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B N001 H001 115.7 . . ?
C00D N001 H001 115.7 . . ?
C00D N001 C00B 128.5(2) . . ?
C00Z N005 C00A 117.0(3) . . ?
N005 C00A C00B 118.1(3) . . ?
N005 C00A C00J 122.4(3) . . ?
C00J C00A C00B 119.5(3) . . ?
N001 C00B C00A 115.4(2) . . ?
C00N C00B N001 124.9(3) . . ?
C00N C00B C00A 119.7(3) . . ?
C00O C00C C00P 124.3(3) . . ?
C00O C00C C00R 117.8(3) . . ?
C00R C00C C00P 117.9(3) . . ?
N001 C00D C00E 114.8(2) . . ?
O003 C00D N001 123.4(3) . . ?
O003 C00D C00E 121.8(3) . . ?
C00D C00E H00A 109.0 . . ?
C00D C00E H00B 109.0 . . ?
H00A C00E H00B 107.8 . . ?
C00G C00E C00D 112.7(2) . . ?
C00G C00E H00A 109.0 . . ?
C00G C00E H00B 109.0 . . ?
C00I C00F C00X 120.0(3) . . ?
C00I C00F C012 119.8(3) . . ?
C012 C00F C00X 120.2(3) . . ?
C00L C00G C00E 114.9(2) . . ?
C00P C00G C00E 126.1(2) . . ?
C00P C00G C00L 118.9(3) . . ?
C00M C00H C00Q 121.9(3) . . ?
C00M C00H C00Y 118.8(3) . . ?
C00Y C00H C00Q 119.3(3) . . ?
C00F C00I H00I 119.6 . . ?
C00M C00I C00F 120.7(3) . . ?
C00M C00I H00I 119.6 . . ?
C00U C00J C00A 117.0(3) . . ?
C00W C00J C00A 119.2(3) . . ?
C00W C00J C00U 123.8(3) . . ?
C00S C00K C011 120.4(3) . . ?
C00V C00K C00S 119.7(3) . . ?
C00V C00K C011 119.9(3) . . ?
C00Q C00L C00G 176.5(3) . . ?
C00H C00M H00M 119.9 . . ?
C00I C00M C00H 120.1(3) . . ?
C00I C00M H00M 119.9 . . ?
C00B C00N H00N 119.9 . . ?
C00B C00N C00T 120.1(3) . . ?
C00T C00N H00N 119.9 . . ?
C00C C00O H00O 119.7 . . ?
C00S C00O C00C 120.7(3) . . ?
C00S C00O H00O 119.7 . . ?
C00C C00P H00P 115.2 . . ?
C00G C00P C00C 129.7(3) . . ?
C00G C00P H00P 115.2 . . ?
C00L C00Q C00H 179.4(4) . . ?
C00C C00R H00R 119.4 . . ?
C00V C00R C00C 121.1(3) . . ?
C00V C00R H00R 119.4 . . ?
C00K C00S H00S 119.8 . . ?
C00O C00S C00K 120.5(3) . . ?
C00O C00S H00S 119.8 . . ?
C00N C00T H00T 119.3 . . ?
C00W C00T C00N 121.4(3) . . ?
C00W C00T H00T 119.3 . . ?
C00J C00U H00U 119.9 . . ?
C010 C00U C00J 120.1(3) . . ?
C010 C00U H00U 119.9 . . ?
C00K C00V C00R 120.1(3) . . ?
C00K C00V H00V 119.9 . . ?
C00R C00V H00V 119.9 . . ?
C00J C00W H00W 120.0 . . ?
C00T C00W C00J 120.1(3) . . ?
C00T C00W H00W 120.0 . . ?
F002 C00X F004 102.4(3) . . ?
F002 C00X C00F 113.0(3) . . ?
F004 C00X C00F 111.7(3) . . ?
F008 C00X F002 107.5(3) . . ?
F008 C00X F004 106.6(3) . . ?
F008 C00X C00F 114.8(3) . . ?
C00H C00Y H00Y 119.7 . . ?
C012 C00Y C00H 120.7(3) . . ?
C012 C00Y H00Y 119.7 . . ?
N005 C00Z H00Z 117.6 . . ?
N005 C00Z C010 124.8(3) . . ?
C010 C00Z H00Z 117.6 . . ?
C00U C010 C00Z 118.6(3) . . ?
C00U C010 H010 120.7 . . ?
C00Z C010 H010 120.7 . . ?
F006 C011 F007 105.9(3) . . ?
F006 C011 C00K 114.4(3) . . ?
F007 C011 C00K 112.2(3) . . ?
F009 C011 F006 104.9(3) . . ?
F009 C011 F007 103.9(3) . . ?
F009 C011 C00K 114.6(3) . . ?
C00F C012 C00Y 119.9(3) . . ?
C00F C012 H012 120.1 . . ?
C00Y C012 H012 120.1 . . ?
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
N001 H001 0.8600 . ?
N001 C00B 1.399(4) . ?
N001 C00D 1.357(3) . ?
F002 C00X 1.318(4) . ?
O003 C00D 1.210(3) . ?
F004 C00X 1.343(4) . ?
N005 C00A 1.365(4) . ?
N005 C00Z 1.313(4) . ?
F006 C011 1.314(4) . ?
F007 C011 1.332(4) . ?
F008 C00X 1.289(4) . ?
F009 C011 1.290(4) . ?
C00A C00B 1.426(4) . ?
C00A C00J 1.412(4) . ?
C00B C00N 1.372(4) . ?
C00C C00O 1.388(4) . ?
C00C C00P 1.468(4) . ?
C00C C00R 1.395(4) . ?
C00D C00E 1.522(4) . ?
C00E H00A 0.9700 . ?
C00E H00B 0.9700 . ?
C00E C00G 1.513(4) . ?
C00F C00I 1.373(4) . ?
C00F C00X 1.489(4) . ?
C00F C012 1.374(4) . ?
C00G C00L 1.434(4) . ?
C00G C00P 1.341(4) . ?
C00H C00M 1.387(4) . ?
C00H C00Q 1.433(4) . ?
C00H C00Y 1.387(4) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.373(4) . ?
C00J C00U 1.411(4) . ?
C00J C00W 1.410(4) . ?
C00K C00S 1.379(4) . ?
C00K C00V 1.367(4) . ?
C00K C011 1.490(4) . ?
C00L C00Q 1.193(4) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00T 1.404(4) . ?
C00O H00O 0.9300 . ?
C00O C00S 1.378(4) . ?
C00P H00P 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00V 1.379(4) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00T C00W 1.362(4) . ?
C00U H00U 0.9300 . ?
C00U C010 1.345(5) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C012 1.377(4) . ?
C00Z H00Z 0.9300 . ?
C00Z C010 1.391(5) . ?
C010 H010 0.9300 . ?
C012 H012 0.9300 . ?
