#------------------------------------------------------------------------------
#$Date: 2016-02-20 01:53:41 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102173.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2102173
loop_
_publ_author_name
'Chisholm, Greig'
'Kennedy, Alan R.'
'Wilson, Sharon'
'Teat, Simon J.'
_publ_section_title
;
 Comparison of the structural motifs of acetoacetanilides and related
 azo pigments
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1046
_journal_page_last               1053
_journal_paper_doi               10.1107/S0108768100010946
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.766(5)
_cell_length_b                   9.3754(18)
_cell_length_c                   8.1729(13)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      9.11
_cell_measurement_theta_min      6.62
_cell_volume                     2050.9(6)
_computing_cell_refinement       'MSC/Rigaku diffractometer control'
_computing_data_collection       'MSC/Rigaku diffractometer control'
_computing_data_reduction        texsan
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type  'Rigaku AFC7S Diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4726
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0480P)²+0.0959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                1401
_reflns_number_total             2363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0031.cif
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.0959P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.0959P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               2102173
_cod_database_fobs_code          2102173
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.25827(4) -0.29631(10) 0.03770(14) 0.0314(3) Uani 1 d .
O2 O 0.17274(5) -0.12578(13) 0.21003(14) 0.0419(3) Uani 1 d .
N1 N 0.29137(4) -0.07245(13) 0.03422(14) 0.0216(3) Uani 1 d .
C1 C 0.34058(5) -0.10045(15) 0.08792(17) 0.0217(3) Uani 1 d .
C2 C 0.37706(5) 0.00066(15) 0.05131(18) 0.0248(3) Uani 1 d .
C3 C 0.42603(6) -0.01927(18) 0.10250(18) 0.0291(3) Uani 1 d .
C4 C 0.43982(5) -0.13953(18) 0.19110(18) 0.0302(3) Uani 1 d .
C5 C 0.40313(6) -0.23921(18) 0.2264(2) 0.0312(3) Uani 1 d .
C6 C 0.35386(5) -0.22121(15) 0.1774(2) 0.0269(3) Uani 1 d .
C7 C 0.25437(5) -0.16820(15) 0.00963(17) 0.0218(3) Uani 1 d .
C8 C 0.20664(5) -0.10706(15) -0.05909(18) 0.0221(3) Uani 1 d .
C9 C 0.16489(5) -0.10829(15) 0.06541(19) 0.0263(3) Uani 1 d .
C10 C 0.11356(7) -0.0837(3) -0.0007(3) 0.0444(5) Uani 1 d .
C41 C 0.49270(6) -0.1597(2) 0.2518(2) 0.0476(5) Uani 1 d .
H41A H 0.4960 -0.2544 0.3014 0.057 Uiso 0.50 calc PR
H41B H 0.5004 -0.0865 0.3336 0.057 Uiso 0.50 calc PR
H41C H 0.5160 -0.1512 0.1598 0.057 Uiso 0.50 calc PR
H41D H 0.5123 -0.0737 0.2285 0.057 Uiso 0.50 calc PR
H41E H 0.5079 -0.2416 0.1963 0.057 Uiso 0.50 calc PR
H41F H 0.4923 -0.1768 0.3701 0.057 Uiso 0.50 calc PR
H1 H 0.3675(5) 0.0820(19) -0.012(2) 0.026(4) Uiso 1 d .
H2 H 0.4495(6) 0.059(2) 0.077(2) 0.039(5) Uiso 1 d .
H3 H 0.4122(6) -0.3239(19) 0.288(2) 0.036(5) Uiso 1 d .
H4 H 0.3303(6) -0.2908(18) 0.206(2) 0.034(5) Uiso 1 d .
H5 H 0.2843(6) 0.016(2) 0.011(2) 0.029(4) Uiso 1 d .
H6 H 0.2103(5) -0.0112(17) -0.0939(18) 0.019(4) Uiso 1 d .
H7 H 0.1981(5) -0.1678(17) -0.153(2) 0.024(4) Uiso 1 d .
H8 H 0.1113(8) 0.011(3) -0.046(3) 0.061(6) Uiso 1 d .
H9 H 0.1063(9) -0.153(3) -0.088(3) 0.078(8) Uiso 1 d .
H10 H 0.0900(9) -0.087(3) 0.082(4) 0.078(8) Uiso 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 0.0286(5) 0.0204(5) 0.0453(7) 0.0010(4) -0.0056(5) -0.0015(4)
O2 0.0507(7) 0.0514(7) 0.0237(6) 0.0076(5) 0.0060(5) 0.0185(6)
N1 0.0212(6) 0.0178(6) 0.0257(6) 0.0008(5) -0.0016(5) 0.0012(4)
C1 0.0213(6) 0.0235(7) 0.0202(7) -0.0012(5) 0.0007(5) 0.0007(5)
C2 0.0274(8) 0.0238(7) 0.0232(7) 0.0015(6) -0.0014(6) -0.0014(6)
C3 0.0248(8) 0.0363(8) 0.0262(8) 0.0014(7) -0.0005(6) -0.0062(6)
C4 0.0225(7) 0.0430(9) 0.0249(7) 0.0025(7) -0.0001(6) 0.0025(6)
C5 0.0280(7) 0.0344(8) 0.0310(8) 0.0080(7) -0.0007(6) 0.0063(7)
C6 0.0253(7) 0.0269(8) 0.0285(8) 0.0033(6) 0.0019(6) 0.0003(6)
C7 0.0235(7) 0.0209(7) 0.0210(6) -0.0027(5) 0.0002(5) -0.0010(5)
C8 0.0244(7) 0.0217(7) 0.0202(6) -0.0004(5) -0.0017(5) -0.0028(5)
C9 0.0287(7) 0.0224(7) 0.0278(7) 0.0035(6) 0.0025(6) 0.0050(6)
C10 0.0264(9) 0.0579(12) 0.0488(11) 0.0159(10) 0.0048(8) 0.0084(8)
C41 0.0253(8) 0.0708(13) 0.0465(10) 0.0149(10) -0.0037(7) 0.0023(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C1 127.28(12)
C2 C1 C6 119.11(13)
C2 C1 N1 117.40(13)
C6 C1 N1 123.47(13)
C3 C2 C1 120.35(14)
C2 C3 C4 121.13(14)
C5 C4 C3 117.84(14)
C5 C4 C41 120.72(15)
C3 C4 C41 121.41(15)
C4 C5 C6 122.08(14)
C5 C6 C1 119.48(14)
O1 C7 N1 124.06(13)
O1 C7 C8 120.88(12)
N1 C7 C8 115.06(12)
C7 C8 C9 111.88(12)
O2 C9 C10 122.20(15)
O2 C9 C8 121.97(13)
C10 C9 C8 115.81(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2273(17)
O2 C9 1.2117(18)
N1 C7 1.3516(18)
N1 C1 1.4129(17)
C1 C2 1.3935(19)
C1 C6 1.394(2)
C2 C3 1.388(2)
C3 C4 1.390(2)
C4 C5 1.386(2)
C4 C41 1.512(2)
C5 C6 1.389(2)
C7 C8 1.5088(19)
C8 C9 1.511(2)
C9 C10 1.494(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N1 C1 C2 157.92(13)
C7 N1 C1 C6 -23.5(2)
C6 C1 C2 C3 0.4(2)
N1 C1 C2 C3 179.08(13)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 0.2(2)
C2 C3 C4 C41 -178.04(16)
C3 C4 C5 C6 -0.6(2)
C41 C4 C5 C6 177.65(16)
C4 C5 C6 C1 0.9(2)
C2 C1 C6 C5 -0.8(2)
N1 C1 C6 C5 -179.38(14)
C1 N1 C7 O1 3.0(2)
C1 N1 C7 C8 -176.08(13)
O1 C7 C8 C9 70.81(18)
N1 C7 C8 C9 -110.10(14)
C7 C8 C9 O2 15.5(2)
C7 C8 C9 C10 -165.72(15)
