#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:11:48 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239282.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_7239282
loop_
_publ_author_name
'Sathesh, Venkatesan'
'Sathishkumar, Munusamy'
'Ramachandran, Gunasekar'
'Rathore, Ravindranath S.'
'Sathiyanarayanan, Kulathu Iyer'
_publ_section_title
;
 A green approach for the one-pot multi-component synthesis of
 N-substituted γ, δ and ε-lactams involving C--N bond formation
 catalyzed by FeCl3
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              23035
_journal_paper_doi               10.1039/c3ra44472d
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C18 H16 F N2 O2'
_chemical_formula_sum            'C18 H16 F N2 O2'
_chemical_formula_weight         311.33
_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_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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.505(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2658(4)
_cell_length_b                   15.6654(7)
_cell_length_c                   12.7267(6)
_cell_measurement_reflns_used    5977
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.58
_cell_volume                     1571.63(13)
_computing_cell_refinement       'APEXII (Bruker, 2012)'
_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 & PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16484
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.28
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1161P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.2014
_reflns_number_gt                2398
_reflns_number_total             3531
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ra44472d.txt
_cod_data_source_block           4b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7239282
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
H2 H 0.039(4) 0.2747(19) 1.035(3) 0.082(9) Uiso 1 1 d .
N1 N 0.2110(2) 0.21742(11) 0.88632(13) 0.0431(4) Uani 1 1 d .
O2 O 0.3122(2) -0.07284(11) 1.24051(14) 0.0642(5) Uani 1 1 d .
C1 C 0.0686(2) 0.18927(13) 0.92472(16) 0.0423(5) Uani 1 1 d .
H1 H -0.0169 0.1638 0.8618 0.051 Uiso 1 1 calc R
N2 N -0.0096(2) 0.25841(12) 0.96383(15) 0.0480(5) Uani 1 1 d .
F1 F 0.3940(2) -0.06685(10) 1.05792(13) 0.0762(5) Uani 1 1 d .
C12 C 0.1281(2) 0.12060(13) 1.01156(15) 0.0408(5) Uani 1 1 d .
O1 O 0.1126(2) 0.17258(11) 0.70773(12) 0.0603(5) Uani 1 1 d .
C6 C -0.0979(2) 0.32223(13) 0.89407(16) 0.0442(5) Uani 1 1 d .
C17 C 0.0768(3) 0.11697(14) 1.10555(17) 0.0490(5) Uani 1 1 d .
H17 H 0.0017 0.1579 1.1161 0.059 Uiso 1 1 calc R
C2 C 0.2204(3) 0.20608(13) 0.78292(16) 0.0447(5) Uani 1 1 d .
C11 C -0.1768(3) 0.30997(16) 0.78207(18) 0.0532(6) Uani 1 1 d .
H11 H -0.1634 0.2586 0.7491 0.064 Uiso 1 1 calc R
C13 C 0.2356(3) 0.05697(14) 0.99673(17) 0.0489(5) Uani 1 1 d .
H13 H 0.2710 0.0568 0.9339 0.059 Uiso 1 1 calc R
C15 C 0.2441(3) -0.00808(13) 1.16986(17) 0.0474(5) Uani 1 1 d .
C16 C 0.1343(3) 0.05401(15) 1.18395(18) 0.0540(6) Uani 1 1 d .
H16 H 0.0988 0.0535 1.2467 0.065 Uiso 1 1 calc R
C14 C 0.2895(3) -0.00531(14) 1.07402(18) 0.0493(5) Uani 1 1 d .
C7 C -0.1158(3) 0.40094(15) 0.93848(19) 0.0552(6) Uani 1 1 d .
H7 H -0.0601 0.4115 1.0125 0.066 Uiso 1 1 calc R
C10 C -0.2746(3) 0.37368(19) 0.7202(2) 0.0640(7) Uani 1 1 d .
H10 H -0.3279 0.3644 0.6456 0.077 Uiso 1 1 calc R
C5 C 0.3557(3) 0.26102(18) 0.95928(19) 0.0621(7) Uani 1 1 d .
H5 H 0.3753 0.2734 1.0335 0.075 Uiso 1 1 calc R
C3 C 0.3883(3) 0.24102(17) 0.77928(19) 0.0599(6) Uani 1 1 d .
H3 H 0.4336 0.2378 0.7208 0.072 Uiso 1 1 calc R
C8 C -0.2150(4) 0.46417(17) 0.8749(2) 0.0699(7) Uani 1 1 d .
H8 H -0.2272 0.5163 0.9066 0.084 Uiso 1 1 calc R
C9 C -0.2955(3) 0.45017(19) 0.7653(2) 0.0706(8) Uani 1 1 d .
H9 H -0.3634 0.4923 0.7224 0.085 Uiso 1 1 calc R
C18 C 0.2849(5) -0.0713(2) 1.3455(2) 0.0863(9) Uani 1 1 d .
H18A H 0.3281 -0.0189 1.3824 0.130 Uiso 1 1 calc R
H18B H 0.3426 -0.1186 1.3887 0.130 Uiso 1 1 calc R
H18C H 0.1656 -0.0754 1.3364 0.130 Uiso 1 1 calc R
C4 C 0.4674(4) 0.2820(2) 0.8892(2) 0.0801(9) Uani 1 1 d .
H4 H 0.5665 0.3142 0.9099 0.096 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
C2 N1 C5 114.06(17)
C2 N1 C1 124.74(17)
C5 N1 C1 121.20(15)
C15 O2 C18 117.2(2)
N2 C1 N1 112.36(16)
N2 C1 C12 111.50(15)
N1 C1 C12 109.82(16)
N2 C1 H1 107.6
N1 C1 H1 107.6
C12 C1 H1 107.6
C6 N2 C1 121.99(17)
C6 N2 H2 115.1(19)
C1 N2 H2 116.7(19)
C17 C12 C13 117.62(19)
C17 C12 C1 122.88(17)
C13 C12 C1 119.48(16)
C7 C6 N2 118.73(19)
C7 C6 C11 117.8(2)
N2 C6 C11 123.4(2)
C16 C17 C12 121.63(19)
C16 C17 H17 119.2
C12 C17 H17 119.2
O1 C2 N1 125.44(19)
O1 C2 C3 126.75(18)
N1 C2 C3 107.80(19)
C10 C11 C6 120.1(2)
C10 C11 H11 120.0
C6 C11 H11 120.0
C14 C13 C12 120.06(18)
C14 C13 H13 120.0
C12 C13 H13 120.0
O2 C15 C16 126.74(19)
O2 C15 C14 116.03(19)
C16 C15 C14 117.2(2)
C15 C16 C17 120.47(19)
C15 C16 H16 119.8
C17 C16 H16 119.8
F1 C14 C13 119.15(18)
F1 C14 C15 117.91(19)
C13 C14 C15 122.94(19)
C8 C7 C6 121.2(2)
C8 C7 H7 119.4
C6 C7 H7 119.4
C9 C10 C11 121.7(2)
C9 C10 H10 119.2
C11 C10 H10 119.2
N1 C5 C4 105.04(18)
N1 C5 H5 127.5
C4 C5 H5 127.5
C4 C3 C2 105.93(18)
C4 C3 H3 127.0
C2 C3 H3 127.0
C9 C8 C7 120.1(3)
C9 C8 H8 119.9
C7 C8 H8 119.9
C10 C9 C8 119.1(2)
C10 C9 H9 120.5
C8 C9 H9 120.5
O2 C18 H18A 109.5
O2 C18 H18B 109.5
H18A C18 H18B 109.5
O2 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C3 C4 C5 106.7(2)
C3 C4 H4 126.6
C5 C4 H4 126.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.353(2)
N1 C5 1.446(3)
N1 C1 1.471(2)
O2 C15 1.360(3)
O2 C18 1.421(3)
C1 N2 1.426(3)
C1 C12 1.514(3)
C1 H1 0.9800
N2 C6 1.389(3)
N2 H2 0.91(3)
F1 C14 1.350(2)
C12 C17 1.385(3)
C12 C13 1.386(3)
O1 C2 1.214(3)
C6 C7 1.383(3)
C6 C11 1.391(3)
C17 C16 1.382(3)
C17 H17 0.9300
C2 C3 1.505(3)
C11 C10 1.374(3)
C11 H11 0.9300
C13 C14 1.362(3)
C13 H13 0.9300
C15 C16 1.378(3)
C15 C14 1.381(3)
C16 H16 0.9300
C7 C8 1.381(4)
C7 H7 0.9300
C10 C9 1.362(4)
C10 H10 0.9300
C5 C4 1.501(3)
C5 H5 0.9300
C3 C4 1.498(4)
C3 H3 0.9300
C8 C9 1.371(4)
C8 H8 0.9300
C9 H9 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C4 H4 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 N1 C1 N2 -120.6(2)
C5 N1 C1 N2 59.2(3)
C2 N1 C1 C12 114.6(2)
C5 N1 C1 C12 -65.6(2)
N1 C1 N2 C6 66.7(2)
C12 C1 N2 C6 -169.54(17)
N2 C1 C12 C17 14.0(3)
N1 C1 C12 C17 139.24(19)
N2 C1 C12 C13 -167.43(18)
N1 C1 C12 C13 -42.2(2)
C1 N2 C6 C7 -156.31(19)
C1 N2 C6 C11 26.9(3)
C13 C12 C17 C16 2.1(3)
C1 C12 C17 C16 -179.4(2)
C5 N1 C2 O1 -178.6(2)
C1 N1 C2 O1 1.2(3)
C5 N1 C2 C3 2.2(3)
C1 N1 C2 C3 -177.95(19)
C7 C6 C11 C10 -2.7(3)
N2 C6 C11 C10 174.15(19)
C17 C12 C13 C14 -1.2(3)
C1 C12 C13 C14 -179.78(19)
C18 O2 C15 C16 -8.1(3)
C18 O2 C15 C14 172.4(2)
O2 C15 C16 C17 179.1(2)
C14 C15 C16 C17 -1.4(3)
C12 C17 C16 C15 -0.7(4)
C12 C13 C14 F1 179.86(19)
C12 C13 C14 C15 -1.1(3)
O2 C15 C14 F1 1.0(3)
C16 C15 C14 F1 -178.6(2)
O2 C15 C14 C13 -178.1(2)
C16 C15 C14 C13 2.4(3)
N2 C6 C7 C8 -174.1(2)
C11 C6 C7 C8 2.8(3)
C6 C11 C10 C9 0.9(3)
C2 N1 C5 C4 2.1(3)
C1 N1 C5 C4 -177.7(2)
O1 C2 C3 C4 175.2(2)
N1 C2 C3 C4 -5.7(3)
C6 C7 C8 C9 -1.2(4)
C11 C10 C9 C8 0.9(4)
C7 C8 C9 C10 -0.7(4)
C2 C3 C4 C5 6.8(3)
N1 C5 C4 C3 -5.5(3)
