# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0D-118
_database_code_depnum_ccdc_archive 'CCDC 1040237'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            0D-118
_chemical_name_systematic        'But-2-ynoic acid triclinic polymorph'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0156(5)
_cell_length_b                   6.9262(9)
_cell_length_c                   7.0836(8)
_cell_angle_alpha                112.956(12)
_cell_angle_beta                 97.227(10)
_cell_angle_gamma                107.388(11)
_cell_volume                     207.85(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    605
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      29.2524
_cell_measurement_theta_min      4.4210
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2333
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.317
_diffrn_reflns_theta_min         4.430
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   -5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00  -46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3710  178.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3710   37.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3710  -37.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega  -22.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3710  -99.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  8 omega   -6.00   62.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3710   37.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
  9 omega   -6.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3710   37.0000  -60.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0305043000
_diffrn_orient_matrix_UB_12      0.0996189000
_diffrn_orient_matrix_UB_13      0.0429607000
_diffrn_orient_matrix_UB_21      0.0079915000
_diffrn_orient_matrix_UB_22      -0.0051645000
_diffrn_orient_matrix_UB_23      0.0985100000
_diffrn_orient_matrix_UB_31      0.1509105000
_diffrn_orient_matrix_UB_32      0.0672084000
_diffrn_orient_matrix_UB_33      0.0353431000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                697
_reflns_number_total             980
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0811P)²+0.0292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1630
_refine_special_details          
;
All carbon bonded hydrogens are placed in calculated 
positions. Hydrogen atoms of the carboxylic 
acid group have been refined isotropically.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2191(3) 0.0976(2) -0.0917(2) 0.0378(4) Uani 1 1 d . . . . .
O2 O -0.2515(3) 0.2172(3) 0.2442(2) 0.0389(4) Uani 1 1 d . . . . .
C4 C 0.6877(4) 0.7370(3) 0.3559(3) 0.0361(5) Uani 1 1 d . . . . .
H4A H 0.6731 0.8736 0.4610 0.054 Uiso 1 1 calc GR . . . .
H4B H 0.7593 0.7681 0.2441 0.054 Uiso 1 1 calc GR . . . .
H4C H 0.8228 0.6928 0.4264 0.054 Uiso 1 1 calc GR . . . .
C3 C 0.4025(4) 0.5537(3) 0.2612(3) 0.0313(5) Uani 1 1 d . . . . .
C1 C -0.1174(4) 0.2267(3) 0.1020(3) 0.0300(5) Uani 1 1 d . . . . .
C2 C 0.1684(4) 0.4040(3) 0.1852(3) 0.0328(5) Uani 1 1 d . . . . .
H2 H -0.444(7) 0.093(7) 0.172(6) 0.111(12) Uiso 1 1 d . . . . .

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
O1 0.0317(8) 0.0339(8) 0.0350(9) 0.0131(7) 0.0047(6) 0.0011(6)
O2 0.0273(7) 0.0406(9) 0.0373(9) 0.0137(7) 0.0086(6) 0.0033(6)
C4 0.0295(10) 0.0297(10) 0.0373(11) 0.0126(9) 0.0060(8) 0.0005(8)
C3 0.0297(10) 0.0288(10) 0.0327(11) 0.0131(8) 0.0085(8) 0.0088(8)
C1 0.0256(9) 0.0274(9) 0.0369(11) 0.0156(9) 0.0082(8) 0.0088(7)
C2 0.0300(10) 0.0288(10) 0.0355(11) 0.0131(9) 0.0084(8) 0.0082(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.239(2) . ?
O2 C1 1.291(2) . ?
O2 H2 0.99(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.455(3) . ?
C3 C2 1.192(3) . ?
C1 C2 1.442(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 109(2) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.4(2) . . ?
O1 C1 O2 124.42(17) . . ?
O1 C1 C2 121.00(16) . . ?
O2 C1 C2 114.58(17) . . ?
C3 C2 C1 177.6(2) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0D-154
_database_code_depnum_ccdc_archive 'CCDC 1040238'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            0D-154
_chemical_name_systematic        'But-2-ynoic acid triclinic polymorph'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0359(9)
_cell_length_b                   6.9758(13)
_cell_length_c                   7.1152(13)
_cell_angle_alpha                112.963(18)
_cell_angle_beta                 97.033(16)
_cell_angle_gamma                107.706(17)
_cell_volume                     210.80(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    595
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      29.1708
_cell_measurement_theta_min      5.2751
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2347
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.235
_diffrn_reflns_theta_min         5.286
_diffrn_ambient_temperature      154(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00    4.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   22.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -99.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00  -11.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4960  -57.0000  150.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   37.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3710  -57.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega   -5.00   91.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3710   37.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00   61.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3710  -19.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   88.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3710   57.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega   32.00   90.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3710 -178.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   95.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.3710  178.0000   60.0000 60
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0305562000
_diffrn_orient_matrix_UB_12      0.0987755000
_diffrn_orient_matrix_UB_13      0.0423664000
_diffrn_orient_matrix_UB_21      0.0081431000
_diffrn_orient_matrix_UB_22      -0.0045422000
_diffrn_orient_matrix_UB_23      0.0983160000
_diffrn_orient_matrix_UB_31      0.1504887000
_diffrn_orient_matrix_UB_32      0.0673870000
_diffrn_orient_matrix_UB_33      0.0349080000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                622
_reflns_number_total             976
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         976
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0894P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1719
_refine_special_details          
;
All carbon bonded hydrogens are placed in 
calculated positions. Hydrogen atoms of the 
carboxylic acid group have been refined 
isotropically.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-H2
 0.86 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2184(3) 0.0984(2) -0.0912(2) 0.0466(5) Uani 1 1 d . . . . .
O2 O -0.2523(3) 0.2156(3) 0.2426(2) 0.0491(5) Uani 1 1 d D . . . .
C4 C 0.6875(4) 0.7358(3) 0.3557(3) 0.0458(6) Uani 1 1 d . . . . .
H4A H 0.6728 0.8727 0.4578 0.069 Uiso 1 1 calc GR . . . .
H4B H 0.7616 0.7641 0.2440 0.069 Uiso 1 1 calc GR . . . .
H4C H 0.8201 0.6932 0.4288 0.069 Uiso 1 1 calc GR . . . .
C3 C 0.4007(4) 0.5525(3) 0.2609(3) 0.0389(5) Uani 1 1 d . . . . .
C1 C -0.1181(4) 0.2258(3) 0.1018(3) 0.0370(5) Uani 1 1 d . . . . .
C2 C 0.1680(4) 0.4041(3) 0.1861(3) 0.0409(6) Uani 1 1 d . . . . .
H2 H -0.429(5) 0.102(5) 0.176(5) 0.135(14) Uiso 1 1 d D . . . .

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
O1 0.0374(8) 0.0448(9) 0.0436(9) 0.0167(7) 0.0080(7) 0.0036(6)
O2 0.0318(8) 0.0543(10) 0.0494(10) 0.0195(8) 0.0117(7) 0.0064(7)
C4 0.0324(10) 0.0417(12) 0.0503(13) 0.0186(10) 0.0066(9) 0.0022(9)
C3 0.0328(10) 0.0378(11) 0.0412(12) 0.0160(9) 0.0088(9) 0.0103(9)
C1 0.0294(9) 0.0362(10) 0.0466(12) 0.0205(9) 0.0095(9) 0.0121(8)
C2 0.0340(10) 0.0389(11) 0.0456(12) 0.0180(9) 0.0095(9) 0.0107(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.239(2) . ?
O2 C1 1.287(2) . ?
O2 H2 0.903(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.463(3) . ?
C3 C2 1.186(2) . ?
C1 C2 1.449(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 108(2) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.3(2) . . ?
O1 C1 O2 124.66(17) . . ?
O1 C1 C2 120.91(16) . . ?
O2 C1 C2 114.43(17) . . ?
C3 C2 C1 178.0(2) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0D-190
_database_code_depnum_ccdc_archive 'CCDC 1040239'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            0D-190
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0580(9)
_cell_length_b                   7.0169(17)
_cell_length_c                   7.1325(15)
_cell_angle_alpha                112.92(2)
_cell_angle_beta                 96.962(17)
_cell_angle_gamma                108.002(19)
_cell_volume                     213.14(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    534
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      29.0545
_cell_measurement_theta_min      4.6815
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2311
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.119
_diffrn_reflns_theta_min         4.691
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -78.00   -7.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  150.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   20.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -88.00    3.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -37.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -59.00   -5.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega  -21.00   56.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -99.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -53.00    2.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -37.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega  -38.00   51.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega  -25.00   59.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -99.0000  150.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0317462000
_diffrn_orient_matrix_UB_12      0.0974683000
_diffrn_orient_matrix_UB_13      0.0418235000
_diffrn_orient_matrix_UB_21      0.0049879000
_diffrn_orient_matrix_UB_22      -0.0058648000
_diffrn_orient_matrix_UB_23      0.0973510000
_diffrn_orient_matrix_UB_31      0.1499963000
_diffrn_orient_matrix_UB_32      0.0683125000
_diffrn_orient_matrix_UB_33      0.0372935000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                572
_reflns_number_total             996
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0958P)²+0.0061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.2136
_refine_special_details          
;
All carbon bonded hydrogens are placed in 
calculated positions. Hydrogen atoms of the 
carboxylic acid group have been refined isotropically.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2171(4) 0.0990(3) -0.0907(3) 0.0563(7) Uani 1 1 d . . . . .
O2 O -0.2536(4) 0.2139(3) 0.2414(3) 0.0594(7) Uani 1 1 d . . . . .
C4 C 0.6860(5) 0.7348(4) 0.3551(4) 0.0559(8) Uani 1 1 d . . . . .
H4A H 0.6775 0.8632 0.4724 0.084 Uiso 1 1 calc GR . . . .
H4B H 0.7457 0.7794 0.2476 0.084 Uiso 1 1 calc GR . . . .
H4C H 0.8263 0.6849 0.4081 0.084 Uiso 1 1 calc GR . . . .
C3 C 0.4012(5) 0.5514(4) 0.2612(4) 0.0475(7) Uani 1 1 d . . . . .
C1 C -0.1183(5) 0.2268(4) 0.1032(4) 0.0458(7) Uani 1 1 d . . . . .
C2 C 0.1681(5) 0.4032(4) 0.1860(4) 0.0505(7) Uani 1 1 d . . . . .
H2 H -0.445(11) 0.086(8) 0.169(7) 0.17(2) Uiso 1 1 d . . . . .

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
O1 0.0445(10) 0.0550(12) 0.0531(11) 0.0220(9) 0.0100(8) 0.0034(9)
O2 0.0393(10) 0.0647(13) 0.0582(12) 0.0228(10) 0.0143(9) 0.0065(9)
C4 0.0409(14) 0.0503(16) 0.0584(16) 0.0216(14) 0.0089(12) 0.0009(11)
C3 0.0397(13) 0.0449(14) 0.0514(15) 0.0206(12) 0.0128(11) 0.0099(11)
C1 0.0352(12) 0.0455(14) 0.0584(16) 0.0265(12) 0.0142(11) 0.0133(10)
C2 0.0409(13) 0.0484(16) 0.0578(15) 0.0235(13) 0.0141(12) 0.0124(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.248(3) . ?
O2 C1 1.281(3) . ?
O2 H2 0.99(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.459(3) . ?
C3 C2 1.189(3) . ?
C1 C2 1.447(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 109(3) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.4(3) . . ?
O1 C1 O2 124.4(2) . . ?
O1 C1 C2 120.1(2) . . ?
O2 C1 C2 115.5(2) . . ?
C3 C2 C1 177.5(3) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0D-226
_database_code_depnum_ccdc_archive 'CCDC 1040240'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            0D-226
_chemical_name_systematic        'But-2-ynoic acid triclinic polymorph'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0673(8)
_cell_length_b                   7.0638(13)
_cell_length_c                   7.1630(9)
_cell_angle_alpha                113.064(16)
_cell_angle_beta                 96.689(12)
_cell_angle_gamma                108.347(15)
_cell_volume                     215.30(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    507
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      28.6229
_cell_measurement_theta_min      4.6795
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2279
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.686
_diffrn_reflns_theta_min         4.689
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -37.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   -7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -85.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -77.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega  -51.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -77.0000 -150.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0312769000
_diffrn_orient_matrix_UB_12      0.0970765000
_diffrn_orient_matrix_UB_13      0.0410753000
_diffrn_orient_matrix_UB_21      0.0061212000
_diffrn_orient_matrix_UB_22      -0.0041408000
_diffrn_orient_matrix_UB_23      0.0976986000
_diffrn_orient_matrix_UB_31      0.1500187000
_diffrn_orient_matrix_UB_32      0.0682929000
_diffrn_orient_matrix_UB_33      0.0359959000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                592
_reflns_number_total             997
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1043P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2071
_refine_special_details          
;
All carbon bonded hydrogens are placed in 
calculated positions. Hydrogen atoms of the 
carboxylic acid group have been refined isotropically.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2165(3) 0.1003(3) -0.0895(3) 0.0643(6) Uani 1 1 d . . . . .
O2 O -0.2546(4) 0.2117(3) 0.2394(3) 0.0666(6) Uani 1 1 d . . . . .
C4 C 0.6849(5) 0.7327(4) 0.3540(4) 0.0627(7) Uani 1 1 d . . . . .
H4A H 0.6713 0.8672 0.4543 0.094 Uiso 1 1 calc GR . . . .
H4B H 0.7577 0.7600 0.2437 0.094 Uiso 1 1 calc GR . . . .
H4C H 0.8156 0.6922 0.4260 0.094 Uiso 1 1 calc GR . . . .
C3 C 0.4003(5) 0.5510(4) 0.2613(4) 0.0531(6) Uani 1 1 d . . . . .
C1 C -0.1176(5) 0.2269(4) 0.1040(4) 0.0499(6) Uani 1 1 d . . . . .
C2 C 0.1682(5) 0.4024(4) 0.1857(4) 0.0547(7) Uani 1 1 d . . . . .
H2 H -0.459(10) 0.085(8) 0.168(7) 0.21(2) Uiso 1 1 d . . . . .

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
O1 0.0506(11) 0.0614(11) 0.0580(12) 0.0225(9) 0.0092(8) 0.0017(8)
O2 0.0452(10) 0.0729(12) 0.0626(11) 0.0255(9) 0.0159(9) 0.0065(8)
C4 0.0466(14) 0.0538(13) 0.0653(15) 0.0251(12) 0.0052(12) -0.0016(10)
C3 0.0462(13) 0.0498(12) 0.0580(14) 0.0241(11) 0.0138(11) 0.0131(10)
C1 0.0403(12) 0.0457(11) 0.0617(14) 0.0271(11) 0.0109(11) 0.0120(9)
C2 0.0463(13) 0.0499(12) 0.0603(15) 0.0242(11) 0.0111(11) 0.0121(10)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.248(3) . ?
O2 C1 1.275(3) . ?
O2 H2 1.03(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 C3 1.453(3) . ?
C3 C2 1.186(3) . ?
C1 C2 1.443(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 111(2) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.9(3) . . ?
O1 C1 O2 123.9(2) . . ?
O1 C1 C2 119.8(2) . . ?
O2 C1 C2 116.3(2) . . ?
C3 C2 C1 177.0(2) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_0D-262-(transformed_to_1D)
_database_code_depnum_ccdc_archive 'CCDC 1040241'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            0D-262
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9158(11)
_cell_length_b                   7.1104(10)
_cell_length_c                   7.871(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.59(3)
_cell_angle_gamma                90
_cell_volume                     215.40(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    315
_cell_measurement_temperature    262(2)
_cell_measurement_theta_max      28.9724
_cell_measurement_theta_min      5.2605
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1882
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.036
_diffrn_reflns_theta_min         5.271
_diffrn_ambient_temperature      262(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   21.00   2.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -60.0000 20

#__ type_ start__ end____ width___ exp.time_
  2 omega  -51.00   45.00   2.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -37.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   90.00   2.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585   37.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega  -11.00   65.00   2.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585   77.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega  -86.00  -44.00   2.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  150.0000 21

#__ type_ start__ end____ width___ exp.time_
  6 omega  -47.00   53.00   2.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  -90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0192626000
_diffrn_orient_matrix_UB_12      0.0977980000
_diffrn_orient_matrix_UB_13      -0.0132309000
_diffrn_orient_matrix_UB_21      -0.1164162000
_diffrn_orient_matrix_UB_22      -0.0064051000
_diffrn_orient_matrix_UB_23      -0.0801998000
_diffrn_orient_matrix_UB_31      -0.1415726000
_diffrn_orient_matrix_UB_32      0.0185490000
_diffrn_orient_matrix_UB_33      0.0423602000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                495
_reflns_number_total             939
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     57
_refine_ls_number_reflns         939
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1602
_refine_ls_wR_factor_ref         0.1981
_refine_special_details          
;
All hydrogen atoms are placed in calculated position.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.7478(18) 0.2334(11) 0.7772(9) 0.0559(17) Uani 1 1 d . . . . .
C3 C 0.8299(17) 0.3571(8) 0.6938(9) 0.0523(16) Uani 1 1 d . . . . .
O2 O 0.6564(18) -0.0827(6) 0.8227(7) 0.0743(18) Uani 1 1 d . . . . .
H2 H 0.6371 -0.1589 0.8986 0.111 Uiso 1 1 calc GR . . . .
C4 C 0.9296(19) 0.5118(11) 0.5956(11) 0.066(2) Uani 1 1 d . . . . .
H4A H 0.9061 0.6275 0.6552 0.099 Uiso 1 1 calc GR . . . .
H4B H 0.7823 0.5149 0.4838 0.099 Uiso 1 1 calc GR . . . .
H4C H 1.1668 0.4962 0.5824 0.099 Uiso 1 1 calc GR . . . .
O1 O 0.5361(13) 0.1193(6) 1.0162(6) 0.0636(14) Uani 1 1 d . . . . .
C1 C 0.6363(17) 0.0897(9) 0.8827(9) 0.0519(16) Uani 1 1 d . . . . .

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
C2 0.071(4) 0.045(3) 0.055(4) 0.001(3) 0.021(3) -0.002(4)
C3 0.060(4) 0.046(4) 0.052(4) 0.004(3) 0.013(3) 0.002(3)
O2 0.118(5) 0.044(3) 0.069(4) 0.000(3) 0.040(3) -0.003(3)
C4 0.067(5) 0.060(4) 0.071(6) 0.015(4) 0.015(4) -0.002(4)
O1 0.094(3) 0.043(3) 0.060(3) 0.004(3) 0.031(2) 0.000(3)
C1 0.061(4) 0.040(4) 0.053(4) 0.004(4) 0.006(3) -0.001(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.178(9) . ?
C2 C1 1.434(10) . ?
C3 C4 1.439(9) . ?
O2 H2 0.8200 . ?
O2 C1 1.321(8) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
O1 C1 1.206(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 176.9(7) . . ?
C2 C3 C4 178.4(7) . . ?
C1 O2 H2 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C1 C2 114.2(6) . . ?
O1 C1 C2 124.2(7) . . ?
O1 C1 O2 121.6(6) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d-118
_database_code_depnum_ccdc_archive 'CCDC 1040242'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8248(8)
_cell_length_b                   7.0987(7)
_cell_length_c                   7.7801(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.058(15)
_cell_angle_gamma                90
_cell_volume                     207.32(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    463
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      29.1114
_cell_measurement_theta_min      3.9114
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1149
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_min         3.919
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   77.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -19.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   37.0000 -150.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0515484000
_diffrn_orient_matrix_UB_12      -0.0961115000
_diffrn_orient_matrix_UB_13      -0.0062805000
_diffrn_orient_matrix_UB_21      -0.1810850000
_diffrn_orient_matrix_UB_22      0.0269911000
_diffrn_orient_matrix_UB_23      -0.0089747000
_diffrn_orient_matrix_UB_31      -0.0154033000
_diffrn_orient_matrix_UB_32      0.0039155000
_diffrn_orient_matrix_UB_33      -0.0922833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.514
_reflns_Friedel_fraction_full    0.668
_reflns_Friedel_fraction_max     0.520
_reflns_number_gt                728
_reflns_number_total             786
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_coef       .
_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     60
_refine_ls_number_reflns         786
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.0566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0973
_refine_special_details          
;

Carbon bonded hydrogens are placed in calculated 
positions.Hydrogen atoms of the carboxylic acid group 
have been isotropically refined.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0616(9) 0.2988(5) 0.9088(4) 0.0293(8) Uani 1 1 d . . . . .
H4A H -0.0293 0.3492 1.0090 0.044 Uiso 1 1 calc GR . . . .
H4B H 0.2686 0.2184 0.9510 0.044 Uiso 1 1 calc GR . . . .
H4C H -0.1249 0.2244 0.8350 0.044 Uiso 1 1 calc GR . . . .
C3 C 0.1658(8) 0.4529(4) 0.8075(4) 0.0230(6) Uani 1 1 d . . . . .
C1 C 0.3621(8) 0.7243(4) 0.6160(3) 0.0234(7) Uani 1 1 d . . . . .
O1 O 0.4698(7) 0.6937(3) 0.4817(3) 0.0277(5) Uani 1 1 d . . . . .
C2 C 0.2527(8) 0.5782(4) 0.7235(4) 0.0241(6) Uani 1 1 d . . . . .
O2 O 0.3355(7) 0.8950(3) 0.6792(3) 0.0318(6) Uani 1 1 d . . . . .
H2 H 0.405(10) 0.979(5) 0.610(5) 0.040(10) Uiso 1 1 d . . . . .

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
C4 0.0346(19) 0.0233(16) 0.0312(16) 0.0058(12) 0.0092(14) -0.0010(14)
C3 0.0262(15) 0.0202(13) 0.0229(13) -0.0016(11) 0.0052(11) 0.0024(12)
C1 0.0262(17) 0.0185(15) 0.0251(14) 0.0043(12) 0.0035(11) 0.0007(13)
O1 0.0413(13) 0.0190(10) 0.0262(10) 0.0029(9) 0.0149(9) 0.0030(10)
C2 0.0288(16) 0.0177(13) 0.0262(14) -0.0007(11) 0.0062(12) 0.0009(12)
O2 0.0521(16) 0.0168(9) 0.0306(12) 0.0011(9) 0.0180(10) -0.0001(10)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.448(4) . ?
C3 C2 1.189(4) . ?
C1 O1 1.214(3) . ?
C1 C2 1.444(4) . ?
C1 O2 1.319(4) . ?
O2 H2 0.88(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.4(3) . . ?
O1 C1 C2 123.7(3) . . ?
O1 C1 O2 123.2(3) . . ?
O2 C1 C2 113.1(2) . . ?
C3 C2 C1 177.5(3) . . ?
C1 O2 H2 110(2) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1D-154
_database_code_depnum_ccdc_archive 'CCDC 1040243'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            1D-154
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8518(5)
_cell_length_b                   7.0956(5)
_cell_length_c                   7.7924(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.862(12)
_cell_angle_gamma                90
_cell_volume                     209.16(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    462
_cell_measurement_temperature    154(2)
_cell_measurement_theta_max      28.4910
_cell_measurement_theta_min      5.3400
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1275
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.597
_diffrn_reflns_theta_min         5.329
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      154(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   22.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   41.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366  -77.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -61.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000 -120.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0513130000
_diffrn_orient_matrix_UB_12      -0.0961149000
_diffrn_orient_matrix_UB_13      0.0062804000
_diffrn_orient_matrix_UB_21      0.1797571000
_diffrn_orient_matrix_UB_22      0.0271117000
_diffrn_orient_matrix_UB_23      0.0087549000
_diffrn_orient_matrix_UB_31      0.0151451000
_diffrn_orient_matrix_UB_32      0.0039571000
_diffrn_orient_matrix_UB_33      0.0920683000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.725
_reflns_number_gt                764
_reflns_number_total             894
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         894
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.0168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          
;
Carbon bonded hydrogens are placed in 
calculated positions.Hydrogen atoms of the 
carboxylic acid group have been isotropically refined.
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0613(10) 0.2995(5) 0.9075(4) 0.0356(8) Uani 1 1 d . . . . .
H4A H -0.0282 0.3503 1.0078 0.053 Uiso 1 1 calc GR . . . .
H4B H 0.2660 0.2186 0.9492 0.053 Uiso 1 1 calc GR . . . .
H4C H -0.1247 0.2256 0.8342 0.053 Uiso 1 1 calc GR . . . .
C3 C 0.1656(8) 0.4530(4) 0.8063(4) 0.0278(7) Uani 1 1 d . . . . .
C1 C 0.3624(9) 0.7238(4) 0.6150(4) 0.0295(7) Uani 1 1 d . . . . .
O1 O 0.4681(7) 0.6936(3) 0.4818(3) 0.0355(6) Uani 1 1 d . . . . .
C2 C 0.2536(8) 0.5786(5) 0.7233(4) 0.0301(7) Uani 1 1 d . . . . .
O2 O 0.3378(7) 0.8948(3) 0.6790(3) 0.0400(7) Uani 1 1 d . . . . .
H2 H 0.419(11) 0.973(6) 0.608(6) 0.071(15) Uiso 1 1 d . . . . .

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
C4 0.043(2) 0.0277(16) 0.037(2) 0.0066(14) 0.0107(15) -0.0002(15)
C3 0.0297(16) 0.0256(15) 0.0289(15) -0.0010(12) 0.0075(12) 0.0021(13)
C1 0.0359(19) 0.0217(16) 0.0312(16) 0.0034(14) 0.0070(13) 0.0023(15)
O1 0.0564(15) 0.0232(11) 0.0317(12) 0.0025(11) 0.0204(10) 0.0027(12)
C2 0.0349(17) 0.0227(14) 0.0342(16) -0.0008(13) 0.0101(13) 0.0002(13)
O2 0.0676(18) 0.0214(10) 0.0359(13) 0.0002(11) 0.0222(12) 0.0002(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.446(4) . ?
C3 C2 1.187(4) . ?
C1 O1 1.203(4) . ?
C1 C2 1.444(5) . ?
C1 O2 1.322(4) . ?
O2 H2 0.88(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.5(3) . . ?
O1 C1 C2 124.0(3) . . ?
O1 C1 O2 123.3(3) . . ?
O2 C1 C2 112.7(3) . . ?
C3 C2 C1 176.9(3) . . ?
C1 O2 H2 106(3) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1D-190
_database_code_depnum_ccdc_archive 'CCDC 1040244'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            1D-190
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8856(13)
_cell_length_b                   7.1138(12)
_cell_length_c                   7.8353(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.93(3)
_cell_angle_gamma                90
_cell_volume                     212.65(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    395
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      29.1215
_cell_measurement_theta_min      3.8935
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1358
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.779
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.186
_diffrn_reflns_theta_min         3.901
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   44.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega   42.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   77.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147   57.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147 -140.0000  165.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -50.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -57.0000  -60.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0507284000
_diffrn_orient_matrix_UB_12      -0.0958687000
_diffrn_orient_matrix_UB_13      0.0061633000
_diffrn_orient_matrix_UB_21      0.1783517000
_diffrn_orient_matrix_UB_22      0.0270493000
_diffrn_orient_matrix_UB_23      0.0087409000
_diffrn_orient_matrix_UB_31      0.0146902000
_diffrn_orient_matrix_UB_32      0.0038758000
_diffrn_orient_matrix_UB_33      0.0915174000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.659
_reflns_number_gt                753
_reflns_number_total             899
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         899
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          
;
All carbon bonded hydrogens are placed in 
calculated positions. Hydrogen atoms of the 
carboxylic group have isotropically refined.
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0617(10) 0.3004(5) 0.9075(4) 0.0424(9) Uani 1 1 d . . . . .
H4A H 0.0079 0.3506 1.0159 0.064 Uiso 1 1 calc GR . . . .
H4B H 0.2533 0.2092 0.9343 0.064 Uiso 1 1 calc GR . . . .
H4C H -0.1466 0.2384 0.8411 0.064 Uiso 1 1 calc GR . . . .
C3 C 0.1664(8) 0.4536(4) 0.8050(4) 0.0326(7) Uani 1 1 d . . . . .
C1 C 0.3623(9) 0.7239(5) 0.6149(4) 0.0348(7) Uani 1 1 d . . . . .
O1 O 0.4679(7) 0.6934(3) 0.4825(3) 0.0421(7) Uani 1 1 d . . . . .
C2 C 0.2521(8) 0.5781(5) 0.7232(4) 0.0335(7) Uani 1 1 d . . . . .
O2 O 0.3382(8) 0.8946(3) 0.6787(3) 0.0474(7) Uani 1 1 d . . . . .
H2 H 0.409(10) 0.967(6) 0.602(5) 0.053(12) Uiso 1 1 d . . . . .

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
C4 0.050(2) 0.0354(18) 0.042(2) 0.0092(15) 0.0098(17) -0.0023(15)
C3 0.0354(16) 0.0313(16) 0.0316(15) 0.0014(13) 0.0079(13) 0.0032(13)
C1 0.0408(19) 0.0299(18) 0.0324(15) 0.0033(15) 0.0039(14) 0.0022(15)
O1 0.0641(16) 0.0282(12) 0.0392(12) 0.0032(12) 0.0229(11) 0.0033(11)
C2 0.0375(17) 0.0278(15) 0.0361(16) -0.0012(14) 0.0094(13) 0.0016(13)
O2 0.0785(19) 0.0264(11) 0.0433(14) -0.0002(11) 0.0265(13) 0.0005(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.457(5) . ?
C3 C2 1.178(4) . ?
C1 O1 1.206(4) . ?
C1 C2 1.454(5) . ?
C1 O2 1.323(4) . ?
O2 H2 0.87(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.5(3) . . ?
O1 C1 C2 124.0(3) . . ?
O1 C1 O2 123.4(3) . . ?
O2 C1 C2 112.6(3) . . ?
C3 C2 C1 176.7(3) . . ?
C1 O2 H2 103(2) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1D-226
_database_code_depnum_ccdc_archive 'CCDC 1040245'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            1D-226
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8912(10)
_cell_length_b                   7.1141(12)
_cell_length_c                   7.8453(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.80(2)
_cell_angle_gamma                90
_cell_volume                     213.32(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    393
_cell_measurement_temperature    226(2)
_cell_measurement_theta_max      28.7023
_cell_measurement_theta_min      5.2811
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1266
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.766
_diffrn_reflns_theta_min         5.292
_diffrn_ambient_temperature      226(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   22.00   1.0000    7.1900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   49.00   1.0000    7.1900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -70.00    4.00   1.0000    7.1900
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -37.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   41.00   1.0000    7.1900
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -57.0000  -60.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0509236000
_diffrn_orient_matrix_UB_12      -0.0959323000
_diffrn_orient_matrix_UB_13      0.0059158000
_diffrn_orient_matrix_UB_21      0.1777246000
_diffrn_orient_matrix_UB_22      0.0271389000
_diffrn_orient_matrix_UB_23      0.0089790000
_diffrn_orient_matrix_UB_31      0.0137634000
_diffrn_orient_matrix_UB_32      0.0035671000
_diffrn_orient_matrix_UB_33      0.0914072000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                752
_reflns_number_total             909
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_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     60
_refine_ls_number_reflns         909
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          
;
All carbon bonded hydrogens are placed in 
calculated positions. Hydrogen atoms of the 
carboxylic acid group have been plased from refinement.
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0656(10) 0.3006(6) 0.9066(5) 0.0476(10) Uani 1 1 d . . . . .
H4A H 0.0182 0.3493 1.0153 0.071 Uiso 1 1 calc GR . . . .
H4B H 0.2539 0.2094 0.9300 0.071 Uiso 1 1 calc GR . . . .
H4C H -0.1431 0.2406 0.8426 0.071 Uiso 1 1 calc GR . . . .
C3 C 0.1672(9) 0.4539(5) 0.8045(4) 0.0351(8) Uani 1 1 d . . . . .
C1 C 0.3611(9) 0.7245(5) 0.6148(4) 0.0371(8) Uani 1 1 d . . . . .
O1 O 0.4672(8) 0.6929(3) 0.4826(3) 0.0463(8) Uani 1 1 d . . . . .
C2 C 0.2524(9) 0.5788(6) 0.7228(5) 0.0374(8) Uani 1 1 d . . . . .
O2 O 0.3410(8) 0.8943(3) 0.6784(3) 0.0523(8) Uani 1 1 d . . . . .
H2 H 0.410(10) 0.977(6) 0.599(5) 0.066(14) Uiso 1 1 d . . . . .

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
C4 0.050(3) 0.041(2) 0.053(2) 0.0110(18) 0.012(2) -0.0017(18)
C3 0.0331(18) 0.0349(18) 0.0368(17) 0.0005(15) 0.0051(14) 0.0023(15)
C1 0.044(2) 0.0304(18) 0.0356(16) 0.0027(16) 0.0040(15) 0.0029(17)
O1 0.0747(19) 0.0310(13) 0.0391(13) 0.0040(13) 0.0256(12) 0.0050(14)
C2 0.0420(19) 0.0317(17) 0.0394(17) -0.0002(16) 0.0101(15) 0.0037(16)
O2 0.088(2) 0.0293(12) 0.0447(14) -0.0006(13) 0.0273(14) -0.0007(14)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 C3 1.451(5) . ?
C3 C2 1.179(5) . ?
C1 O1 1.207(4) . ?
C1 C2 1.451(6) . ?
C1 O2 1.315(4) . ?
O2 H2 0.93(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.4(4) . . ?
O1 C1 C2 123.6(3) . . ?
O1 C1 O2 123.5(3) . . ?
O2 C1 C2 113.0(3) . . ?
C3 C2 C1 176.7(4) . . ?
C1 O2 H2 106(2) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1D-262
_database_code_depnum_ccdc_archive 'CCDC 1040246'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            1D-262
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9127(7)
_cell_length_b                   7.1074(8)
_cell_length_c                   7.8489(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.422(16)
_cell_angle_gamma                90
_cell_volume                     214.67(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    333
_cell_measurement_temperature    262(2)
_cell_measurement_theta_max      25.4400
_cell_measurement_theta_min      5.2960
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1284
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.673
_diffrn_reflns_theta_min         5.283
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      262(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   22.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   41.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   41.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147  -57.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00    4.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  -30.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0496039000
_diffrn_orient_matrix_UB_12      -0.0961659000
_diffrn_orient_matrix_UB_13      0.0055306000
_diffrn_orient_matrix_UB_21      0.1771061000
_diffrn_orient_matrix_UB_22      0.0267043000
_diffrn_orient_matrix_UB_23      0.0096703000
_diffrn_orient_matrix_UB_31      0.0117584000
_diffrn_orient_matrix_UB_32      0.0031180000
_diffrn_orient_matrix_UB_33      0.0911636000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.625
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.661
_reflns_number_gt                671
_reflns_number_total             879
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 237 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         879
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.0098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          
;
All carbon bonded hydrogens are placed in calculated 
positions. Hydrogen atom of the carboxylic acid 
group have been isotropically refined.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0664(11) 0.3011(6) 0.9056(5) 0.0583(11) Uani 1 1 d . . . . .
H4A H -0.0093 0.3504 1.0065 0.087 Uiso 1 1 calc GR . . . .
H4B H 0.2607 0.2187 0.9406 0.087 Uiso 1 1 calc GR . . . .
H4C H -0.1203 0.2325 0.8367 0.087 Uiso 1 1 calc GR . . . .
C3 C 0.1689(9) 0.4545(5) 0.8050(5) 0.0447(8) Uani 1 1 d . . . . .
C1 C 0.3631(10) 0.7234(5) 0.6155(4) 0.0477(9) Uani 1 1 d . . . . .
O1 O 0.4664(8) 0.6926(3) 0.4829(3) 0.0564(8) Uani 1 1 d . . . . .
C2 C 0.2532(10) 0.5797(6) 0.7231(5) 0.0468(9) Uani 1 1 d . . . . .
O2 O 0.3419(9) 0.8942(4) 0.6786(4) 0.0642(9) Uani 1 1 d . . . . .
H2 H 0.409(11) 0.975(7) 0.601(6) 0.079(16) Uiso 1 1 d . . . . .

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
C4 0.065(3) 0.050(2) 0.061(3) 0.013(2) 0.013(2) -0.001(2)
C3 0.0495(19) 0.0402(19) 0.0448(17) 0.0006(16) 0.0097(15) 0.0035(16)
C1 0.061(2) 0.038(2) 0.0432(17) 0.0027(18) 0.0081(16) 0.005(2)
O1 0.086(2) 0.0393(14) 0.0503(14) 0.0022(14) 0.0297(12) 0.0040(15)
C2 0.055(2) 0.0369(17) 0.0498(18) -0.0005(17) 0.0129(16) 0.0020(17)
O2 0.106(2) 0.0364(13) 0.0563(16) -0.0009(14) 0.0322(16) -0.0005(16)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 C3 1.445(5) . ?
C3 C2 1.179(5) . ?
C1 O1 1.203(4) . ?
C1 C2 1.440(6) . ?
C1 O2 1.319(4) . ?
O2 H2 0.91(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.9(5) . . ?
O1 C1 C2 124.1(4) . . ?
O1 C1 O2 123.1(3) . . ?
O2 C1 C2 112.8(3) . . ?
C3 C2 C1 176.2(4) . . ?
C1 O2 H2 107(3) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1D-298
_database_code_depnum_ccdc_archive 'CCDC 1040247'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_audit_creation_date             2014-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014/6
_chemical_name_common            1D-298
_chemical_name_systematic        'But-2-ynoic acid'
_chemical_formula_moiety         'C4 H4 O2'
_chemical_formula_sum            'C4 H4 O2'
_chemical_formula_weight         84.07
_chemical_absolute_configuration ?
_chemical_melting_point          ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9417(12)
_cell_length_b                   7.1096(18)
_cell_length_c                   7.878(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.25(3)
_cell_angle_gamma                90
_cell_volume                     217.25(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    272
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.9969
_cell_measurement_theta_min      3.8810
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             88
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1346
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.061
_diffrn_reflns_theta_min         3.889
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   25.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   43.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   77.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00   13.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000    0.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega  -86.00  -61.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2147 -138.0000  164.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0487157000
_diffrn_orient_matrix_UB_12      -0.0960769000
_diffrn_orient_matrix_UB_13      0.0079263000
_diffrn_orient_matrix_UB_21      0.1764167000
_diffrn_orient_matrix_UB_22      0.0264564000
_diffrn_orient_matrix_UB_23      0.0117101000
_diffrn_orient_matrix_UB_31      0.0059721000
_diffrn_orient_matrix_UB_32      0.0048984000
_diffrn_orient_matrix_UB_33      0.0902778000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.538
_reflns_Friedel_fraction_full    0.752
_reflns_Friedel_fraction_max     0.557
_reflns_number_gt                531
_reflns_number_total             858
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_coef       0.15(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         858
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1218
_refine_special_details          
;
Carbon bonded hydrogens are placed in calculated 
positions. Hydrogen atoms of the carboxylic acid 
group have been placed isotropically refined.

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.0687(13) 0.3010(7) 0.9045(6) 0.0698(15) Uani 1 1 d . . . . .
H4A H 0.0219 0.3480 1.0122 0.105 Uiso 1 1 calc GR . . . .
H4B H 0.2519 0.2104 0.9262 0.105 Uiso 1 1 calc GR . . . .
H4C H -0.1348 0.2424 0.8415 0.105 Uiso 1 1 calc GR . . . .
C3 C 0.1700(10) 0.4550(6) 0.8044(5) 0.0515(11) Uani 1 1 d . . . . .
C1 C 0.3640(11) 0.7228(7) 0.6142(5) 0.0556(11) Uani 1 1 d . . . . .
O1 O 0.4660(9) 0.6925(4) 0.4836(4) 0.0690(10) Uani 1 1 d . . . . .
C2 C 0.2559(11) 0.5797(8) 0.7228(6) 0.0543(11) Uani 1 1 d . . . . .
O2 O 0.3437(10) 0.8944(4) 0.6772(4) 0.0765(12) Uani 1 1 d . . . . .
H2 H 0.410(14) 0.985(8) 0.604(7) 0.11(2) Uiso 1 1 d . . . . .

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
C4 0.077(3) 0.057(3) 0.080(3) 0.019(3) 0.024(3) -0.003(3)
C3 0.054(2) 0.048(3) 0.053(2) 0.000(2) 0.0115(18) 0.002(2)
C1 0.070(3) 0.043(3) 0.056(2) 0.007(3) 0.015(2) 0.006(3)
O1 0.107(2) 0.045(2) 0.0636(17) 0.0040(19) 0.0391(15) 0.0041(19)
C2 0.066(3) 0.043(2) 0.056(2) 0.001(2) 0.0174(19) 0.001(2)
O2 0.126(3) 0.040(2) 0.072(2) -0.003(2) 0.0407(19) -0.002(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 C3 1.446(6) . ?
C3 C2 1.180(6) . ?
C1 O1 1.189(5) . ?
C1 C2 1.442(7) . ?
C1 O2 1.325(6) . ?
O2 H2 0.93(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
C2 C3 C4 179.3(5) . . ?
O1 C1 C2 124.5(5) . . ?
O1 C1 O2 122.9(4) . . ?
O2 C1 C2 112.5(4) . . ?
C3 C2 C1 176.0(5) . . ?
C1 O2 H2 111(3) . . ?

#END=====
