#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/63/7206369.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_7206369
loop_
_publ_author_name
'Shang, Wen'
'Hickey, Magali B.'
'Enkelmann, Volker'
'Snider, Barry B.'
'Foxman, Bruce M.'
_publ_section_title
;
 Chemo- and stereospecific solid-state dimerization of lithium
 trans-2-butenoate and lithium trans-2-butenoate formamide solvate
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              4339
_journal_paper_doi               10.1039/c0ce00810a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C5 H8 Li1 N1 O3'
_chemical_formula_sum            'C5 H8 Li N O3'
_chemical_formula_weight         137.06
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-09-16
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 120.1277(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2503(7)
_cell_length_b                   4.9968(3)
_cell_length_c                   14.8231(5)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    120
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1489.46(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6426
_diffrn_reflns_theta_full        28.186
_diffrn_reflns_theta_max         29.985
_diffrn_reflns_theta_min         4.053
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9799
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.0003882
_refine_ls_shift/su_mean         0.0000387
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + ( 0.05P)² + 0.10P]
,where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0925
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0925
_reflns_limit_h_max              28
_reflns_limit_h_min              -32
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1587
_reflns_number_total             2125
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0498
_oxford_refine_ls_scale          5.53(13)
_oxford_reflns_number_all        2124
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Foxi Licroto/DMF 120K'
_cod_data_source_file            c0ce00810a.txt
_cod_data_source_block           compound_12
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        'C5 H8 Li1 N1 O3'
_cod_database_code               7206369
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
FULL LI(1,X'S, U'S) UNTIL C(5)
CONT H(11,X'S,U[ISO]) UNTIL LAST
END
;
_iucr_refine_instruction_details_restraints
;
NO
END
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
Li1 Li 0.28870(9) 0.4279(3) 0.30736(14) 0.0157 1.0000 Uani
O1 O 0.30190(3) 0.79844(13) 0.28615(6) 0.0156 1.0000 Uani
O2 O 0.34924(3) 1.19030(12) 0.29111(5) 0.0156 1.0000 Uani
O3 O 0.29435(4) 0.40027(14) 0.44156(6) 0.0204 1.0000 Uani
N1 N 0.30748(5) 0.51537(18) 0.59836(7) 0.0209 1.0000 Uani
C1 C 0.35199(4) 0.93971(17) 0.30451(7) 0.0125 1.0000 Uani
C2 C 0.41679(5) 0.79917(18) 0.34348(8) 0.0184 1.0000 Uani
C3 C 0.47307(5) 0.9230(2) 0.36626(9) 0.0213 1.0000 Uani
C4 C 0.53877(6) 0.7887(3) 0.40434(11) 0.0318 1.0000 Uani
C5 C 0.31699(5) 0.5489(2) 0.51868(8) 0.0183 1.0000 Uani
H11 H 0.2800(8) 0.378(3) 0.5926(12) 0.034(4) 1.0000 Uiso
H12 H 0.3237(7) 0.632(3) 0.6515(12) 0.030(4) 1.0000 Uiso
H21 H 0.4158(7) 0.608(3) 0.3522(11) 0.030(4) 1.0000 Uiso
H31 H 0.4705(8) 1.117(3) 0.3567(12) 0.030(4) 1.0000 Uiso
H41 H 0.5343(9) 0.602(4) 0.4096(14) 0.055(5) 1.0000 Uiso
H42 H 0.5728(10) 0.851(3) 0.4762(15) 0.056(5) 1.0000 Uiso
H43 H 0.5556(9) 0.821(4) 0.3540(15) 0.058(5) 1.0000 Uiso
H51 H 0.3445(7) 0.706(3) 0.5249(11) 0.030(4) 1.0000 Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Li1 0.0148(7) 0.0144(7) 0.0190(8) 0.0007(6) 0.0092(6) -0.0001(6)
O1 0.0119(3) 0.0126(3) 0.0211(3) 0.0012(3) 0.0074(3) -0.0009(3)
O2 0.0158(3) 0.0108(3) 0.0207(4) 0.0013(3) 0.0096(3) 0.0004(3)
O3 0.0243(4) 0.0223(3) 0.0167(3) -0.0017(3) 0.0118(3) -0.0030(3)
N1 0.0266(4) 0.0207(4) 0.0172(4) -0.0036(3) 0.0123(4) -0.0041(4)
C1 0.0124(4) 0.0126(4) 0.0122(4) -0.0001(3) 0.0059(3) -0.0003(3)
C2 0.0125(4) 0.0139(4) 0.0249(5) -0.0006(4) 0.0063(3) 0.0016(4)
C3 0.0139(4) 0.0211(4) 0.0275(5) -0.0025(4) 0.0094(4) 0.0008(4)
C4 0.0137(4) 0.0372(7) 0.0398(7) -0.0065(6) 0.0099(4) 0.0029(5)
C5 0.0175(4) 0.0177(4) 0.0198(5) 0.0011(4) 0.0095(4) 0.0000(4)
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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Li -0.0003 0.0001 1.1282 3.9546 0.7508 1.0524 0.6175 85.3905 0.4653 168.2610
0.0377 'International Tables Vol C 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
_geom_angle_publ_flag
C5 N1 H11 115.9(9) no
C5 N1 H12 121.4(9) no
H11 N1 H12 122.4(12) no
O1 C1 O2 123.27(8) yes
O1 C1 C2 117.46(8) yes
O2 C1 C2 119.26(8) yes
C1 C2 C3 123.63(9) yes
C1 C2 H21 115.5(9) no
C3 C2 H21 120.8(9) no
C2 C3 C4 125.17(10) yes
C2 C3 H31 116.4(9) no
C4 C3 H31 118.4(9) no
C3 C4 H41 109.9(11) no
C3 C4 H42 111.9(10) no
H41 C4 H42 106.2(15) no
C3 C4 H43 110.4(11) no
H41 C4 H43 108.4(14) no
H42 C4 H43 110.0(15) no
N1 C5 O3 124.56(10) yes
N1 C5 H51 114.2(8) no
O3 C5 H51 121.3(8) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.2690(11) yes
O2 C1 1.2644(11) yes
O3 C5 1.2373(12) yes
N1 C5 1.3168(13) yes
N1 H11 0.913(15) no
N1 H12 0.896(15) no
C1 C2 1.4910(13) yes
C2 C3 1.3288(13) yes
C2 H21 0.965(15) no
C3 C4 1.4954(15) yes
C3 H31 0.977(14) no
C4 H41 0.949(19) no
C4 H42 1.005(19) no
C4 H43 1.014(17) no
C5 H51 0.988(14) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 H11 O3 4_556 170.5(14) 0.913(15) 2.072(16) 2.9770(16) yes
N1 H12 O2 6_575 162.1(12) 0.896(15) 2.047(15) 2.9128(16) yes
C2 H21 O2 1_545 146.6(12) 0.965(15) 2.484(15) 3.3319(16) yes
