#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502996.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_1502996
loop_
_publ_author_name
'Haddoub, Rose'
'Touil, Mounia'
'Raimundo, Jean-Manuel'
'Siri, Olivier'
_publ_section_title
;
 Unprecedented tunable tetraazamacrocycles.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2722
_journal_page_last               2725
_journal_paper_doi               10.1021/ol100793g
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H9 F1 N4 O4'
_chemical_formula_sum            'C12 H9 F N4 O4'
_chemical_formula_weight         292.23
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-05-19T13:50:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 114.777(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1272(5)
_cell_length_b                   5.4965(2)
_cell_length_c                   16.8300(8)
_cell_measurement_reflns_used    11024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.97
_cell_measurement_wavelength     0.71073
_cell_volume                     1270.54(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.076
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11024
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.8992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1898
_reflns_number_gt                1767
_reflns_number_total             3015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100793g_si_001.cif
_cod_data_source_block           osmai09
_cod_database_code               1502996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.10676(19) 0.6252(5) 0.32327(16) 0.0482(6) Uani 1 1 d .
C2 C 0.0500(2) 0.8227(5) 0.32694(18) 0.0539(7) Uani 1 1 d .
H2 H 0.0495 0.8639 0.3804 0.065 Uiso 1 1 calc R
C3 C -0.0042(2) 0.9550(5) 0.2553(2) 0.0585(7) Uani 1 1 d .
C4 C -0.0072(2) 0.9001(6) 0.17308(18) 0.0572(7) Uani 1 1 d .
C5 C 0.0458(2) 0.7065(5) 0.16639(18) 0.0564(7) Uani 1 1 d .
H5 H 0.0441 0.6661 0.1121 0.068 Uiso 1 1 calc R
C6 C 0.10179(19) 0.5698(5) 0.23877(17) 0.0501(7) Uani 1 1 d .
C7 C 0.1719(2) 0.5703(5) 0.48208(17) 0.0533(7) Uani 1 1 d .
C8 C 0.2240(2) 0.7798(6) 0.52108(17) 0.0536(7) Uani 1 1 d .
C9 C 0.2378(2) 0.8328(6) 0.60676(19) 0.0656(8) Uani 1 1 d .
H9 H 0.2722 0.9714 0.6344 0.079 Uiso 1 1 calc R
C10 C 0.2009(3) 0.6815(7) 0.6504(2) 0.0784(10) Uani 1 1 d .
H10 H 0.2107 0.7192 0.7074 0.094 Uiso 1 1 calc R
C11 C 0.1500(3) 0.4765(7) 0.6114(2) 0.0804(11) Uani 1 1 d .
H11 H 0.1251 0.376 0.6416 0.097 Uiso 1 1 calc R
C12 C 0.1357(3) 0.4199(6) 0.5272(2) 0.0699(9) Uani 1 1 d .
H12 H 0.1015 0.28 0.5006 0.084 Uiso 1 1 calc R
F1 F -0.05596(15) 1.1400(4) 0.26559(14) 0.0905(7) Uani 1 1 d .
N1 N -0.0627(2) 1.0435(6) 0.0954(2) 0.0733(8) Uani 1 1 d .
N2 N 0.15508(19) 0.3680(5) 0.22501(17) 0.0580(6) Uani 1 1 d .
N3 N 0.16110(18) 0.5010(4) 0.39647(15) 0.0563(6) Uani 1 1 d .
H3 H 0.191 0.3728 0.3916 0.068 Uiso 1 1 calc R
N4 N 0.2578(2) 0.9358(5) 0.47527(16) 0.0660(7) Uani 1 1 d .
H4A H 0.2467 0.9042 0.4219 0.079 Uiso 1 1 calc R
H4B H 0.2898 1.0644 0.5002 0.079 Uiso 1 1 calc R
O1 O -0.0884(2) 1.2460(6) 0.10678(19) 0.1096(10) Uani 1 1 d .
O2 O -0.0792(2) 0.9571(6) 0.02424(16) 0.0965(9) Uani 1 1 d .
O3 O 0.14606(18) 0.3252(4) 0.15023(14) 0.0790(7) Uani 1 1 d .
O4 O 0.20633(19) 0.2413(4) 0.28747(16) 0.0759(7) 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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
N3 C1 C2 120.2(2)
N3 C1 C6 124.2(2)
C2 C1 C6 115.6(2)
C3 C2 C1 122.1(3)
C3 C2 H2 119
C1 C2 H2 119
F1 C3 C2 117.5(3)
F1 C3 C4 120.9(3)
C2 C3 C4 121.6(3)
C5 C4 C3 118.2(3)
C5 C4 N1 119.1(3)
C3 C4 N1 122.7(3)
C4 C5 C6 121.1(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C1 121.4(3)
C5 C6 N2 117.0(2)
C1 C6 N2 121.6(2)
C12 C7 C8 120.8(3)
C12 C7 N3 119.3(3)
C8 C7 N3 119.8(3)
N4 C8 C7 121.1(2)
N4 C8 C9 120.9(3)
C7 C8 C9 117.9(3)
C10 C9 C8 120.5(3)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 121.1(3)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 119.5(3)
C10 C11 H11 120.2
C12 C11 H11 120.2
C11 C12 C7 120.2(3)
C11 C12 H12 119.9
C7 C12 H12 119.9
O2 N1 O1 124.3(3)
O2 N1 C4 118.5(3)
O1 N1 C4 117.1(3)
O4 N2 O3 121.8(3)
O4 N2 C6 119.5(2)
O3 N2 C6 118.7(3)
C1 N3 C7 123.7(2)
C1 N3 H3 118.2
C7 N3 H3 118.2
C8 N4 H4A 120
C8 N4 H4B 120
H4A N4 H4B 120
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.346(3)
C1 C2 1.402(4)
C1 C6 1.425(3)
C2 C3 1.351(4)
C2 H2 0.93
C3 F1 1.339(3)
C3 C4 1.398(4)
C4 C5 1.365(4)
C4 N1 1.454(4)
C5 C6 1.379(4)
C5 H5 0.93
C6 N2 1.446(4)
C7 C12 1.382(4)
C7 C8 1.394(4)
C7 N3 1.432(3)
C8 N4 1.386(4)
C8 C9 1.398(4)
C9 C10 1.373(5)
C9 H9 0.93
C10 C11 1.368(5)
C10 H10 0.93
C11 C12 1.377(5)
C11 H11 0.93
C12 H12 0.93
N1 O2 1.214(4)
N1 O1 1.220(4)
N2 O4 1.228(3)
N2 O3 1.230(3)
N3 H3 0.86
N4 H4A 0.86
N4 H4B 0.86
