#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:29:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179633 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/97/4509797.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509797
loop_
_publ_author_name
'Ugono, Onome'
'Rath, Nigam P.'
'Beatty, Alica M.'
_publ_section_title
;
 Synthesis and Control of Single Layer and Polar 2-D Layered Architectures
 in a Series of Organic Layered Solids
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4595
_journal_paper_doi               10.1021/cg900908n
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C8 H11 F N, C5 H3 N2 O4'
_chemical_formula_sum            'C13 H14 F N3 O4'
_chemical_formula_weight         295.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 118.910(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4915(11)
_cell_length_b                   6.5669(4)
_cell_length_c                   13.6542(9)
_cell_measurement_reflns_used    6524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.69
_cell_measurement_theta_min      2.82
_cell_volume                     1294.44(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11027
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.79
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         5085
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0354
_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)+(0.0541P)²+0.1634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                4694
_reflns_number_total             5085
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900908nsup1.cif
_cod_data_source_block           compound4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1294.44(14)
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4509797
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
F1 F 0.62968(6) 0.9538(2) 1.03642(7) 0.0372(2) Uani 1 1 d .
O1 O 0.83742(5) 0.38885(12) 0.80851(8) 0.01694(16) Uani 1 1 d .
O2 O 0.72182(6) 0.61653(12) 0.73780(8) 0.01755(15) Uani 1 1 d .
O3 O 0.44259(5) 0.09919(12) 0.77090(7) 0.01545(15) Uani 1 1 d .
O4 O 0.50769(5) -0.20671(11) 0.78242(6) 0.01284(13) Uani 1 1 d .
N1 N 0.72313(5) 0.08766(13) 0.78153(7) 0.01018(14) Uani 1 1 d .
N2 N 0.65575(6) -0.02659(12) 0.77841(7) 0.01006(13) Uani 1 1 d .
N3 N 0.91562(6) 0.99012(13) 0.83742(8) 0.01237(14) Uani 1 1 d D
C1 C 0.75205(7) 0.44609(15) 0.77210(9) 0.01231(15) Uani 1 1 d .
C2 C 0.69349(6) 0.28015(14) 0.77504(8) 0.01011(14) Uani 1 1 d .
C3 C 0.60617(6) 0.28671(15) 0.76839(8) 0.01144(15) Uani 1 1 d .
H3 H 0.5702 0.4034 0.7629 0.014 Uiso 1 1 calc R
C4 C 0.58424(7) 0.08445(14) 0.77161(9) 0.01027(14) Uani 1 1 d .
C5 C 0.50594(6) -0.01870(14) 0.77510(7) 0.01022(15) Uani 1 1 d .
C6 C 0.98344(8) 0.99384(18) 0.95917(9) 0.01735(18) Uani 1 1 d .
H6A H 0.9830 1.1308 0.9892 0.021 Uiso 1 1 calc R
H6B H 1.0463 0.9694 0.9695 0.021 Uiso 1 1 calc R
C7 C 0.96270(8) 0.83536(19) 1.02544(9) 0.01765(19) Uani 1 1 d .
H7A H 0.9594 0.6999 0.9919 0.021 Uiso 1 1 calc R
H7B H 1.0151 0.8325 1.1028 0.021 Uiso 1 1 calc R
C8 C 0.87457(7) 0.86927(17) 1.03055(9) 0.01555(17) Uani 1 1 d .
C9 C 0.81479(8) 0.70624(19) 1.01364(9) 0.0198(2) Uani 1 1 d .
H9 H 0.8306 0.5744 0.9995 0.024 Uiso 1 1 calc R
C10 C 0.73288(9) 0.7333(2) 1.01711(10) 0.0253(3) Uani 1 1 d .
H10 H 0.6923 0.6219 1.0050 0.030 Uiso 1 1 calc R
C11 C 0.71160(9) 0.9243(3) 1.03840(10) 0.0256(3) Uani 1 1 d .
C12 C 0.76969(9) 1.0882(2) 1.05957(10) 0.0246(2) Uani 1 1 d .
H12A H 0.7543 1.2181 1.0766 0.030 Uiso 1 1 calc R
C13 C 0.85138(8) 1.05915(19) 1.05536(9) 0.0192(2) Uani 1 1 d .
H13 H 0.8922 1.1709 1.0697 0.023 Uiso 1 1 calc R
H1 H 0.8719(17) 0.469(4) 0.7890(19) 0.037(6) Uiso 1 1 d .
H2 H 0.6613(16) -0.151(3) 0.7823(17) 0.030(5) Uiso 1 1 d .
H3A H 0.9278(13) 1.081(2) 0.8003(14) 0.013(4) Uiso 1 1 d D
H3B H 0.8587(10) 1.003(3) 0.8239(15) 0.022(5) Uiso 1 1 d D
H3C H 0.9203(16) 0.873(2) 0.8094(16) 0.026(5) Uiso 1 1 d 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 0.0000 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
C1 O1 H1 115.9(16)
N2 N1 C2 104.96(8)
N1 N2 C4 112.80(8)
N1 N2 H2 119.8(17)
C4 N2 H2 127.4(17)
C6 N3 H3A 112.4(12)
C6 N3 H3B 112.8(12)
H3A N3 H3B 109.9(18)
C6 N3 H3C 108.8(13)
H3A N3 H3C 104.6(19)
H3B N3 H3C 108(2)
O2 C1 O1 125.19(10)
O2 C1 C2 122.52(9)
O1 C1 C2 112.28(9)
N1 C2 C3 111.33(8)
N1 C2 C1 118.48(8)
C3 C2 C1 130.15(9)
C4 C3 C2 104.19(9)
C4 C3 H3 127.9
C2 C3 H3 127.9
N2 C4 C3 106.71(8)
N2 C4 C5 119.82(8)
C3 C4 C5 133.37(9)
O4 C5 O3 126.44(9)
O4 C5 C4 118.20(8)
O3 C5 C4 115.35(8)
N3 C6 C7 112.89(9)
N3 C6 H6A 109.0
C7 C6 H6A 109.0
N3 C6 H6B 109.0
C7 C6 H6B 109.0
H6A C6 H6B 107.8
C8 C7 C6 115.21(10)
C8 C7 H7A 108.5
C6 C7 H7A 108.5
C8 C7 H7B 108.5
C6 C7 H7B 108.5
H7A C7 H7B 107.5
C13 C8 C9 118.13(11)
C13 C8 C7 121.90(10)
C9 C8 C7 119.94(10)
C10 C9 C8 121.18(13)
C10 C9 H9 119.4
C8 C9 H9 119.4
C11 C10 C9 118.58(13)
C11 C10 H10 120.7
C9 C10 H10 120.7
F1 C11 C10 118.87(14)
F1 C11 C12 118.65(14)
C10 C11 C12 122.47(12)
C11 C12 C13 118.32(13)
C11 C12 H12A 120.8
C13 C12 H12A 120.8
C12 C13 C8 121.25(12)
C12 C13 H13 119.4
C8 C13 H13 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C11 1.3521(15)
O1 C1 1.3015(12)
O1 H1 0.90(3)
O2 C1 1.2226(12)
O3 C5 1.2791(12)
O4 C5 1.2379(12)
N1 N2 1.3244(11)
N1 C2 1.3427(12)
N2 C4 1.3510(13)
N2 H2 0.82(2)
N3 C6 1.4890(14)
N3 H3A 0.865(14)
N3 H3B 0.868(15)
N3 H3C 0.880(15)
C1 C2 1.4694(13)
C2 C3 1.3991(13)
C3 C4 1.3829(13)
C3 H3 0.9500
C4 C5 1.4792(13)
C6 C7 1.5224(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5050(16)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C13 1.3932(17)
C8 C9 1.3969(16)
C9 C10 1.3857(18)
C9 H9 0.9500
C10 C11 1.371(2)
C10 H10 0.9500
C11 C12 1.376(2)
C12 C13 1.3891(18)
C12 H12A 0.9500
C13 H13 0.9500
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 N2 C4 -0.80(11)
N2 N1 C2 C3 0.35(11)
N2 N1 C2 C1 -177.67(8)
O2 C1 C2 N1 160.54(10)
O1 C1 C2 N1 -18.78(13)
O2 C1 C2 C3 -17.06(17)
O1 C1 C2 C3 163.63(10)
N1 C2 C3 C4 0.18(11)
C1 C2 C3 C4 177.91(10)
N1 N2 C4 C3 0.93(12)
N1 N2 C4 C5 -175.85(8)
C2 C3 C4 N2 -0.64(11)
C2 C3 C4 C5 175.52(10)
N2 C4 C5 O4 -1.17(14)
C3 C4 C5 O4 -176.93(11)
N2 C4 C5 O3 178.35(9)
C3 C4 C5 O3 2.59(16)
N3 C6 C7 C8 -66.49(13)
C6 C7 C8 C13 -46.84(15)
C6 C7 C8 C9 135.22(11)
C13 C8 C9 C10 2.43(16)
C7 C8 C9 C10 -179.55(10)
C8 C9 C10 C11 -0.47(17)
C9 C10 C11 F1 176.77(10)
C9 C10 C11 C12 -1.91(19)
F1 C11 C12 C13 -176.50(11)
C10 C11 C12 C13 2.19(18)
C11 C12 C13 C8 -0.08(17)
C9 C8 C13 C12 -2.15(16)
C7 C8 C13 C12 179.87(10)
