#------------------------------------------------------------------------------
#$Date: 2019-11-08 00:53:35 +0100 (vie 08 de nov de 2019) $
#$Revision: 224605 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/23/7232300.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_7232300
loop_
_publ_author_name
'Senadi, Gopal Chandru'
'Kudale, Vishal Suresh'
'Wang, Jeh-Jeng'
_publ_section_title
;
 Sustainable methine sources for the synthesis of heterocycles under
 metal- and peroxide-free conditions
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              979
_journal_paper_doi               10.1039/C8GC03839B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C14 H9 F N2 O'
_chemical_formula_sum            'C14 H9 F N2 O'
_chemical_formula_weight         240.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-11-28 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.718(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4895(9)
_cell_length_b                   7.7667(5)
_cell_length_c                   11.5802(6)
_cell_measurement_reflns_used    1186
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.1130
_cell_measurement_theta_min      3.1900
_cell_volume                     1115.59(12)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5038
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0789P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1854
_reflns_number_gt                1565
_reflns_number_total             2592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8gc03839b2.cif
_cod_data_source_block           rp10145
_cod_depositor_comments
'Adding full bibliography for 7232299--7232300.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7232300
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F F -0.37691(11) 0.1203(2) 0.65911(13) 0.0835(5) Uani 1 1 d .
O O 0.06765(12) 0.22387(19) 0.93510(11) 0.0533(5) Uani 1 1 d .
N1 N 0.06557(13) 0.0863(2) 0.76072(13) 0.0386(4) Uani 1 1 d .
N2 N 0.22554(14) -0.0016(2) 0.68397(14) 0.0492(5) Uani 1 1 d .
C1 C 0.11847(16) 0.1592(2) 0.86191(15) 0.0392(5) Uani 1 1 d .
C2 C 0.23534(16) 0.1519(2) 0.86897(16) 0.0405(5) Uani 1 1 d .
C3 C 0.29845(19) 0.2288(3) 0.9627(2) 0.0554(6) Uani 1 1 d .
H3A H 0.2659 0.2817 1.0217 0.066 Uiso 1 1 calc R
C4 C 0.4087(2) 0.2255(3) 0.9670(2) 0.0706(8) Uani 1 1 d .
H4A H 0.4507 0.2765 1.0294 0.085 Uiso 1 1 calc R
C5 C 0.4578(2) 0.1480(4) 0.8806(2) 0.0720(8) Uani 1 1 d .
H5A H 0.5326 0.1469 0.8850 0.086 Uiso 1 1 calc R
C6 C 0.39702(18) 0.0715(3) 0.7871(2) 0.0596(7) Uani 1 1 d .
H6A H 0.4307 0.0189 0.7288 0.072 Uiso 1 1 calc R
C7 C 0.28455(16) 0.0738(3) 0.78067(17) 0.0436(5) Uani 1 1 d .
C8 C 0.12300(17) 0.0092(3) 0.67953(17) 0.0454(5) Uani 1 1 d .
H8A H 0.0829 -0.0397 0.6151 0.054 Uiso 1 1 calc R
C9 C -0.05061(15) 0.0953(2) 0.73639(16) 0.0386(5) Uani 1 1 d .
C10 C -0.11609(17) 0.0310(3) 0.81415(18) 0.0468(5) Uani 1 1 d .
H10A H -0.0860 -0.0175 0.8839 0.056 Uiso 1 1 calc R
C11 C -0.22643(18) 0.0392(3) 0.7877(2) 0.0538(6) Uani 1 1 d .
H11A H -0.2718 -0.0031 0.8393 0.065 Uiso 1 1 calc R
C12 C -0.26799(17) 0.1110(3) 0.6840(2) 0.0542(6) Uani 1 1 d .
C13 C -0.20531(19) 0.1735(3) 0.60486(19) 0.0520(6) Uani 1 1 d .
H13A H -0.2362 0.2193 0.5345 0.062 Uiso 1 1 calc R
C14 C -0.09435(16) 0.1670(3) 0.63200(16) 0.0439(5) Uani 1 1 d .
H14A H -0.0495 0.2106 0.5803 0.053 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
C8 N1 C1 120.91(16)
C8 N1 C9 118.45(15)
C1 N1 C9 120.61(15)
C8 N2 C7 115.94(17)
O C1 N1 120.97(18)
O C1 C2 125.13(18)
N1 C1 C2 113.89(16)
C7 C2 C3 119.9(2)
C7 C2 C1 120.15(17)
C3 C2 C1 119.86(19)
C4 C3 C2 119.5(2)
C4 C3 H3A 120.3
C2 C3 H3A 120.3
C3 C4 C5 120.9(2)
C3 C4 H4A 119.5
C5 C4 H4A 119.5
C4 C5 C6 120.6(2)
C4 C5 H5A 119.7
C6 C5 H5A 119.7
C7 C6 C5 119.5(2)
C7 C6 H6A 120.2
C5 C6 H6A 120.2
C2 C7 C6 119.59(19)
C2 C7 N2 122.35(18)
C6 C7 N2 118.06(19)
N2 C8 N1 126.70(18)
N2 C8 H8A 116.7
N1 C8 H8A 116.7
C14 C9 C10 120.83(19)
C14 C9 N1 118.29(17)
C10 C9 N1 120.87(17)
C11 C10 C9 119.50(19)
C11 C10 H10A 120.3
C9 C10 H10A 120.3
C10 C11 C12 118.7(2)
C10 C11 H11A 120.6
C12 C11 H11A 120.6
F C12 C13 118.5(2)
F C12 C11 118.4(2)
C13 C12 C11 123.1(2)
C12 C13 C14 118.2(2)
C12 C13 H13A 120.9
C14 C13 H13A 120.9
C13 C14 C9 119.7(2)
C13 C14 H14A 120.2
C9 C14 H14A 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C12 1.359(2)
O C1 1.225(2)
N1 C8 1.384(2)
N1 C1 1.396(2)
N1 C9 1.447(2)
N2 C8 1.278(2)
N2 C7 1.395(2)
C1 C2 1.453(3)
C2 C7 1.392(3)
C2 C3 1.399(3)
C3 C4 1.372(3)
C3 H3A 0.9300
C4 C5 1.373(4)
C4 H4A 0.9300
C5 C6 1.382(3)
C5 H5A 0.9300
C6 C7 1.398(3)
C6 H6A 0.9300
C8 H8A 0.9300
C9 C14 1.384(3)
C9 C10 1.379(3)
C10 C11 1.378(3)
C10 H10A 0.9300
C11 C12 1.370(3)
C11 H11A 0.9300
C12 C13 1.363(3)
C13 C14 1.386(3)
C13 H13A 0.9300
C14 H14A 0.9300
