#------------------------------------------------------------------------------
#$Date: 2019-11-23 23:44:53 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 235825 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/72/4037225.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_4037225
loop_
_publ_author_name
'Rathore, Vandana'
'Sattar, Moh'
'Kumar, Raushan'
'Kumar, Sangit'
_publ_section_title
;
 Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones,
 and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of
 sp³ and sp² C-H Bonds.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9206
_journal_page_last               9218
_journal_paper_doi               10.1021/acs.joc.6b01771
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C20 H22 F N2 O2'
_chemical_formula_sum            'C20 H22 F N2 O2'
_chemical_formula_weight         341.40
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.200(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4093(5)
_cell_length_b                   15.7964(10)
_cell_length_c                   14.3323(9)
_cell_measurement_reflns_used    9387
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.70
_cell_measurement_theta_min      2.58
_cell_volume                     1900.9(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24165
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             724.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4924
_refine_diff_density_min         -0.4219
_refine_diff_density_rms         0.1061
_refine_ls_d_res_high            0.6983
_refine_ls_d_res_low             10.6053
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0603
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0603
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+0.4435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1647
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3145
_reflns_number_total             5844
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01771_si_003.cif
_cod_data_source_block           VR183
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037225
_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. Others
 Fixed Sof: H5(0.5) F2(0.5) O3(0.5) N3(0.5) F1(0.5) N2(0.5) O2(0.5) H3(0.5)
3.a Ternary CH refined with riding coordinates:
 C18(H18), C15(H15)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C6(H6), C11(H11), C2(H2), C12(H12), C10(H10), C9(H9)
3.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C17(H17a,H17b,H17c), C20(H20a,H20b,H20c), C16(H16a,H16b,
 H16c)
;
_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+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
_atom_site_disorder_group
O1 O 0.24261(15) 0.70844(8) 0.32598(9) 0.0418(3) Uani 1.000000 . .
N1 N 0.12692(16) 0.71956(9) 0.46379(9) 0.0311(3) Uani 1.000000 . .
C8 C 0.50017(19) 0.71257(10) 0.51221(13) 0.0337(4) Uani 1.000000 . .
C5 C 0.6429(2) 0.95792(12) 0.41121(17) 0.0522(6) Uani 1.000000 . .
H5 H 0.7432(2) 0.97905(12) 0.42921(17) 0.0626(7) Uiso 0.500000 R 1
C18 C -0.0188(2) 0.67425(12) 0.42846(13) 0.0385(4) Uani 1.000000 . .
H18 H -0.0882(2) 0.67018(12) 0.48098(13) 0.0462(5) Uiso 1.000000 R .
C7 C 0.40001(19) 0.76924(11) 0.45045(12) 0.0314(4) Uani 1.000000 . .
F2 F 0.8015(3) 0.98733(14) 0.44906(18) 0.0571(7) Uani 0.500000 . -1
C13 C 0.5410(2) 0.63258(11) 0.48112(16) 0.0454(5) Uani 1.000000 . .
H13 H 0.5097(2) 0.61552(11) 0.42077(16) 0.0545(6) Uiso 1.000000 R .
C14 C 0.2484(2) 0.73029(10) 0.40911(12) 0.0299(4) Uani 1.000000 . .
C15 C 0.1328(2) 0.74946(12) 0.56182(12) 0.0367(4) Uani 1.000000 . .
H15 H 0.2335(2) 0.78003(12) 0.57292(12) 0.0440(5) Uiso 1.000000 R .
C4 C 0.5438(3) 1.00514(12) 0.34479(16) 0.0544(6) Uani 1.000000 . .
C6 C 0.5966(2) 0.88499(12) 0.44804(15) 0.0447(5) Uani 1.000000 . .
H6 H 0.6653(2) 0.85694(12) 0.49070(15) 0.0537(6) Uiso 1.000000 R .
C11 C 0.6725(2) 0.60100(15) 0.6298(2) 0.0626(7) Uani 1.000000 . .
H11 H 0.7299(2) 0.56368(15) 0.6690(2) 0.0751(8) Uiso 1.000000 R .
C19 C -0.1109(2) 0.72368(14) 0.35211(14) 0.0474(5) Uani 1.000000 . .
H19a H -0.1304(15) 0.7800(3) 0.3737(4) 0.0711(8) Uiso 1.000000 GR .
H19b H -0.0498(8) 0.7262(8) 0.2976(4) 0.0711(8) Uiso 1.000000 GR .
H19c H -0.2106(8) 0.6960(5) 0.3368(7) 0.0711(8) Uiso 1.000000 GR .
C17 C -0.0003(2) 0.81180(15) 0.57751(15) 0.0525(6) Uani 1.000000 . .
H17a H 0.0000(11) 0.8555(5) 0.5310(6) 0.0788(8) Uiso 1.000000 GR .
H17b H -0.1007(3) 0.7828(2) 0.5729(10) 0.0788(8) Uiso 1.000000 GR .
H17c H 0.0155(10) 0.8365(7) 0.6385(4) 0.0788(8) Uiso 1.000000 GR .
C2 C 0.3369(3) 0.89942(12) 0.36262(13) 0.0438(5) Uani 1.000000 . .
H2 H 0.2334(3) 0.88104(12) 0.34837(13) 0.0526(6) Uiso 1.000000 R .
C20 C 0.0156(3) 0.58459(13) 0.39891(17) 0.0597(7) Uani 1.000000 . .
H20a H 0.0730(17) 0.58551(13) 0.3429(6) 0.0895(10) Uiso 1.000000 GR .
H20b H 0.0785(17) 0.5567(3) 0.4477(5) 0.0895(10) Uiso 1.000000 GR .
H20c H -0.0829(3) 0.5546(3) 0.3874(11) 0.0895(10) Uiso 1.000000 GR .
C12 C 0.6286(2) 0.57815(13) 0.5400(2) 0.0596(7) Uani 1.000000 . .
H12 H 0.6579(2) 0.52530(13) 0.5181(2) 0.0715(8) Uiso 1.000000 R .
O3 O 0.5351(3) 1.1114(2) 0.2501(2) 0.0414(7) Uani 0.500000 . 1
C10 C 0.6313(2) 0.67905(15) 0.66160(17) 0.0569(6) Uani 1.000000 . .
H10 H 0.6598(2) 0.69459(15) 0.72286(17) 0.0683(7) Uiso 1.000000 R .
C16 C 0.1359(3) 0.67498(14) 0.62922(14) 0.0504(5) Uani 1.000000 . .
H16a H 0.0374(7) 0.6443(5) 0.6215(7) 0.0756(8) Uiso 1.000000 GR .
H16b H 0.2228(11) 0.6381(5) 0.6164(7) 0.0756(8) Uiso 1.000000 GR .
H16c H 0.1493(17) 0.69548(15) 0.69222(14) 0.0756(8) Uiso 1.000000 GR .
C9 C 0.5471(2) 0.73547(13) 0.60298(15) 0.0449(5) Uani 1.000000 . .
H9 H 0.5222(2) 0.78900(13) 0.62486(15) 0.0539(6) Uiso 1.000000 R .
C1 C 0.4421(2) 0.84840(11) 0.42330(13) 0.0349(4) Uani 1.000000 . .
C3 C 0.3860(3) 0.97240(15) 0.32676(17) 0.0537(6) Uani 1.000000 . .
N3 N 0.6357(6) 1.0714(2) 0.3173(3) 0.0358(8) Uani 0.500000 . 1
F1 F 0.2585(4) 1.01341(17) 0.2679(2) 0.0734(9) Uani 0.500000 . 1
N2 N 0.5547(6) 1.0703(3) 0.2857(3) 0.0413(9) Uani 0.500000 . -1
O2 O 0.7108(5) 1.0954(2) 0.3029(3) 0.0540(10) Uani 0.500000 . -1
H3 H 0.354(5) 1.003(3) 0.292(3) 0.028(11) Uiso 0.500000 . -1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 N1 C18 120.42(14)
C15 N1 C18 117.45(14)
C15 N1 C14 122.10(14)
C13 C8 C7 119.90(17)
C9 C8 C7 121.59(16)
C9 C8 C13 118.41(17)
C4 C5 F2 123.67(19)
C6 C5 F2 113.7(2)
C6 C5 C4 122.6(2)
H18 C18 N1 106.58(9)
C19 C18 N1 112.06(15)
C19 C18 H18 106.58(11)
C20 C18 N1 112.35(16)
C20 C18 H18 106.58(12)
C20 C18 C19 112.18(16)
C14 C7 C8 115.28(14)
C1 C7 C8 125.11(15)
C1 C7 C14 119.34(15)
H13 C13 C8 119.97(12)
C12 C13 C8 120.1(2)
C12 C13 H13 119.97(14)
N1 C14 O1 122.68(16)
C7 C14 O1 118.61(15)
C7 C14 N1 118.70(15)
H15 C15 N1 107.11(9)
C17 C15 N1 111.22(14)
C17 C15 H15 107.11(11)
C16 C15 N1 110.75(16)
C16 C15 H15 107.11(10)
C16 C15 C17 113.21(16)
C3 C4 C5 115.36(19)
N2 C4 C5 139.5(3)
N2 C4 C3 105.0(3)
H6 C6 C5 119.15(14)
C1 C6 C5 121.7(2)
C1 C6 H6 119.15(11)
C12 C11 H11 120.27(13)
C10 C11 H11 120.27(14)
C10 C11 C12 119.5(2)
H19a C19 C18 109.5
H19b C19 C18 109.5
H19b C19 H19a 109.5
H19c C19 C18 109.5
H19c C19 H19a 109.5
H19c C19 H19b 109.5
H17a C17 C15 109.5
H17b C17 C15 109.5
H17b C17 H17a 109.5
H17c C17 C15 109.5
H17c C17 H17a 109.5
H17c C17 H17b 109.5
C1 C2 H2 119.37(11)
C3 C2 H2 119.37(15)
C3 C2 C1 121.3(2)
H20a C20 C18 109.5
H20b C20 C18 109.5
H20b C20 H20a 109.5
H20c C20 C18 109.5
H20c C20 H20a 109.5
H20c C20 H20b 109.5
C11 C12 C13 121.0(2)
H12 C12 C13 119.49(14)
H12 C12 C11 119.49(13)
H10 C10 C11 119.77(14)
C9 C10 C11 120.5(2)
C9 C10 H10 119.77(14)
H16a C16 C15 109.5
H16b C16 C15 109.5
H16b C16 H16a 109.5
H16c C16 C15 109.5
H16c C16 H16a 109.5
H16c C16 H16b 109.5
C10 C9 C8 120.6(2)
H9 C9 C8 119.72(11)
H9 C9 C10 119.72(14)
C6 C1 C7 122.70(17)
C2 C1 C7 121.49(16)
C2 C1 C6 115.71(17)
C2 C3 C4 123.0(2)
H3 C3 C4 101(3)
H3 C3 C2 136(3)
O2 N2 C4 101.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C14 1.239(2)
N1 C18 1.484(2)
N1 C14 1.333(2)
N1 C15 1.480(2)
C8 C7 1.487(2)
C8 C13 1.389(3)
C8 C9 1.386(3)
C5 H5 0.9300
C5 F2 1.486(3)
C5 C4 1.438(3)
C5 C6 1.334(3)
C18 H18 0.9800
C18 C19 1.520(3)
C18 C20 1.511(3)
C7 C14 1.507(2)
C7 C1 1.362(2)
C13 H13 0.9300
C13 C12 1.387(3)
C15 H15 0.9800
C15 C17 1.517(3)
C15 C16 1.522(3)
C4 C3 1.434(3)
C4 N3 1.372(5)
C4 N2 1.339(5)
C6 H6 0.9300
C6 C1 1.448(3)
C11 H11 0.9300
C11 C12 1.368(4)
C11 C10 1.366(3)
C19 H19a 0.9600
C19 H19b 0.9600
C19 H19c 0.9600
C17 H17a 0.9600
C17 H17b 0.9600
C17 H17c 0.9600
C2 H2 0.9300
C2 C1 1.450(3)
C2 C3 1.337(3)
C20 H20a 0.9600
C20 H20b 0.9600
C20 H20c 0.9600
C12 H12 0.9300
O3 N3 1.397(5)
C10 H10 0.9300
C10 C9 1.391(3)
C16 H16a 0.9600
C16 H16b 0.9600
C16 H16c 0.9600
C9 H9 0.9300
C3 F1 1.477(3)
C3 H3 0.73(5)
N2 O2 1.381(5)
