# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'Ivana Radosavljevic Evans'
;
? # Address for author 1
;
;
? # Footnote for author 1
;
'John Evans'
;
? # Address 2
;
;
? # Footnote 2
;
'J Howard' '' ''
'Mark R Johnson' '' ''
'Stella R Postlethwaite' '' ''

_publ_contact_author_name        'Ivana Radosavljevic Evans'
_publ_contact_author_email       IVANA.RADOSAVLJEVIC@DURHAM.AC.UK

_publ_section_title              
;
Polymorphism and Hydrogen Bonding in Chincomeronic
Acid:
a Variable Temperature Experimental and Computational Study
;
_journal_coden_ASTM              ?
_journal_coeditor_code           ?
_journal_coeditor_name           ?
_journal_coeditor_notes          ?
_journal_date_accepted           ?
_journal_date_from_coeditor      ?
_journal_date_printers_final     ?
_journal_date_printers_first     ?
_journal_date_proofs_in          ?
_journal_date_proofs_out         ?

# PROCESSING SUMMARY (IUCr Office Use Only):
_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_issue                   ?
_journal_name_full               ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_publ_contact_author_address     
;
Chemical Crystallography Laboratory,
Department of Chemistry,
University of Nowhere,
Nowhere, NO1 4T, UK.
;
_publ_contact_author_fax         '+44 1865 000000'

_publ_contact_author_phone       '+44 1865 000000'

# Check this file using the IUCr facility at:
# http://checkcif.iucr.org/

# The content below is held in the file 'script/refcif.dat'. This is a text
# file which you may edit to reflect local conditions.
# Items which need looking at are represented by a '?'.
# Items for which there are choices are prefixed with 'choose from'.

_publ_contact_letter             
;
Please consider this CIF submission for
publication as a Short Format Paper in Acta
Crystallographica E. The figures will be
sent by e-mail.
;
_publ_requested_category         EO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    'Prof William Clegg'
_publ_requested_journal          'Section E'

# Attachment '34pdca_II_120K.cif'

data_CRYSTALS_cifI
_database_code_depnum_ccdc_archive 'CCDC 686367'
_audit_creation_date             07-01-22
_audit_creation_method           CRYSTALS_ver_12.84

_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.5942(14)
_cell_length_b                   7.3317(13)
_cell_length_c                   12.113(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.339(4)
_cell_angle_gamma                90
_cell_volume                     653.4(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '? '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C7 H5 N1 O4
# Dc = 1.70 Fooo = 344.00 Mu = 1.43 M = 167.12
# Found Formula = C7 H5 N1 O4
# Dc = 1.70 FOOO = 344.00 Mu = 1.43 M = 167.12

_chemical_formula_sum            'C7 H5 N1 O4'
_chemical_formula_moiety         'C7 H5 N1 O4'
_chemical_compound_source        ?
_chemical_formula_weight         167.12

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    120

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.143

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_diffrn_measurement_device_type  Unknown
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      120
_diffrn_reflns_number            4209
_reflns_number_total             1707
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections with Friedels Law is 1707
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1840

_diffrn_reflns_theta_min         2.768
_diffrn_reflns_theta_max         29.614
_diffrn_measured_fraction_theta_max 0.925

_diffrn_reflns_theta_full        27.837
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.80
_refine_diff_density_max         0.95

_refine_ls_number_reflns         1250
_refine_ls_number_restraints     1
_refine_ls_number_parameters     130

#_refine_ls_R_factor_ref 0.0792
_refine_ls_wR_factor_ref         0.1504
_refine_ls_goodness_of_fit_ref   0.8061

#_reflns_number_all 1701
_refine_ls_R_factor_all          0.1027
_refine_ls_wR_factor_all         0.1568

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1250
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_gt          0.1504

_refine_ls_shift/su_max          0.000649

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
19.0 25.1 8.01
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.7075(4) -0.0868(4) 0.6903(2) 0.0196 1.0000 Uani . . . . . .
O1 O 0.7399(4) -0.5926(3) 0.5356(2) 0.0270 1.0000 Uani . . . . . .
O4 O 0.7220(4) -0.5978(3) 0.9527(2) 0.0238 1.0000 Uani . . . . . .
C5 C 0.7847(4) -0.0813(4) 0.8034(3) 0.0163 1.0000 Uani D . . . . .
O2 O 0.6116(5) -0.7172(4) 0.6647(3) 0.0395 1.0000 Uani . . . . . .
C3 C 0.7829(4) -0.4063(4) 0.8105(2) 0.0128 1.0000 Uani . . . . . .
C2 C 0.7141(4) -0.4100(4) 0.6910(2) 0.0128 1.0000 Uani . . . . . .
C1 C 0.6757(4) -0.2466(4) 0.6327(3) 0.0153 1.0000 Uani . . . . . .
C4 C 0.8219(4) -0.2387(4) 0.8653(3) 0.0166 1.0000 Uani . . . . . .
O3 O 0.9347(4) -0.6868(4) 0.8650(3) 0.0434 1.0000 Uani . . . . . .
C7 C 0.8185(4) -0.5810(4) 0.8789(2) 0.0153 1.0000 Uani . . . . . .
C6 C 0.6813(4) -0.5893(4) 0.6264(2) 0.0153 1.0000 Uani . . . . . .
H2 H 0.875(5) -0.233(5) 0.946(3) 0.017(9) 1.0000 Uiso . . . . . .
H1 H 0.627(5) -0.243(5) 0.549(3) 0.015(9) 1.0000 Uiso . . . . . .
H3 H 0.822(6) 0.031(4) 0.838(3) 0.035(12) 1.0000 Uiso D . . . . .
H5 H 0.669(6) 0.040(7) 0.648(4) 0.037(12) 1.0000 Uiso . . . . . .
H4 H 0.731(10) -0.750(10) 0.992(6) 0.10(3) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0211(12) 0.0150(13) 0.0243(14) 0.0051(11) 0.0088(10) 0.0039(10)
O1 0.0474(15) 0.0160(11) 0.0233(12) -0.0049(10) 0.0198(11) -0.0042(11)
O4 0.0367(13) 0.0155(11) 0.0240(12) 0.0043(10) 0.0167(10) 0.0020(10)
C5 0.0190(13) 0.0087(13) 0.0225(15) -0.0057(12) 0.0077(11) -0.0041(11)
O2 0.0589(19) 0.0248(13) 0.0478(16) -0.0193(13) 0.0376(15) -0.0238(14)
C3 0.0119(11) 0.0113(13) 0.0162(13) 0.0018(11) 0.0052(10) 0.0007(10)
C2 0.0091(11) 0.0130(13) 0.0170(14) -0.0011(11) 0.0042(9) -0.0001(10)
C1 0.0163(13) 0.0142(14) 0.0162(13) 0.0020(11) 0.0058(10) 0.0005(11)
C4 0.0160(13) 0.0183(15) 0.0159(13) -0.0043(12) 0.0049(10) -0.0033(11)
O3 0.0485(17) 0.0348(16) 0.0591(19) 0.0304(15) 0.0366(15) 0.0281(14)
C7 0.0150(12) 0.0140(14) 0.0155(13) 0.0056(11) 0.0013(10) 0.0032(11)
C6 0.0145(12) 0.0149(13) 0.0155(13) -0.0040(12) 0.0018(10) -0.0014(11)

_refine_ls_extinction_coef       56(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C5 . 1.350(4) yes
N1 . C1 . 1.354(4) yes
N1 . H5 . 1.07(5) no
O1 . H4 4_534 1.27(7) no
O1 . C6 . 1.284(4) yes
O4 . C7 . 1.294(4) yes
O4 . H4 . 1.21(7) no
C5 . C4 . 1.368(4) yes
C5 . H3 . 0.935(18) no
O2 . C6 . 1.224(4) yes
C3 . C2 . 1.412(4) yes
C3 . C4 . 1.393(4) yes
C3 . C7 . 1.513(4) yes
C2 . C1 . 1.385(4) yes
C2 . C6 . 1.518(4) yes
C1 . H1 . 0.99(4) no
C4 . H2 . 0.96(4) no
O3 . C7 . 1.218(4) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 . N1 . C1 . 121.7(3) yes
C5 . N1 . H5 . 117(3) no
C1 . N1 . H5 . 121(2) no
H4 4_534 O1 . C6 . 112(3) no
C7 . O4 . H4 . 112(3) no
N1 . C5 . C4 . 120.7(3) yes
N1 . C5 . H3 . 119(3) no
C4 . C5 . H3 . 120(3) no
C2 . C3 . C4 . 119.2(3) yes
C2 . C3 . C7 . 121.1(3) yes
C4 . C3 . C7 . 119.8(2) yes
C3 . C2 . C1 . 118.9(3) yes
C3 . C2 . C6 . 121.1(3) yes
C1 . C2 . C6 . 120.0(3) yes
C2 . C1 . N1 . 119.9(3) yes
C2 . C1 . H1 . 122(2) no
N1 . C1 . H1 . 119(2) no
C3 . C4 . C5 . 119.5(3) yes
C3 . C4 . H2 . 120(2) no
C5 . C4 . H2 . 120(2) no
C3 . C7 . O4 . 113.9(3) yes
C3 . C7 . O3 . 120.0(3) yes
O4 . C7 . O3 . 126.0(3) yes
C2 . C6 . O1 . 114.3(3) yes
C2 . C6 . O2 . 119.9(3) yes
O1 . C6 . O2 . 125.7(3) yes
O4 . H4 . O1 4_535 179(6) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H5 . O2 1_565 146 1.07 1.85 2.803(2) yes
O4 . H4 . O1 4_535 179 1.21 1.27 2.471(2) yes

# Attachment '34pdca_II_400K.cif'

data_CRYSTALS_cifII
_database_code_depnum_ccdc_archive 'CCDC 686368'
_audit_creation_date             07-01-17
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title '400Kbeta in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.7185(14)
_cell_length_b                   7.3248(13)
_cell_length_c                   12.179(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.884(4)
_cell_angle_gamma                90
_cell_volume                     668.4(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C7 H5 N1 O4
# Dc = 1.66 Fooo = 344.00 Mu = 1.40 M = 167.12
# Found Formula = C7 H5 N1 O4
# Dc = 1.66 FOOO = 344.00 Mu = 1.40 M = 167.12

_chemical_formula_sum            'C7 H5 N1 O4'
_chemical_formula_moiety         'C7 H5 N1 O4'
_chemical_compound_source        ?
_chemical_formula_weight         167.12

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_max          ?

_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.140

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_diffrn_measurement_device_type  Unknown
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            4293
_reflns_number_total             1738
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections with Friedels Law is 1738
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1850

_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         29.772
_diffrn_measured_fraction_theta_max 0.911

_diffrn_reflns_theta_full        27.986
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.58

_refine_ls_number_reflns         998
_refine_ls_number_restraints     0
_refine_ls_number_parameters     130

#_refine_ls_R_factor_ref 0.0792
_refine_ls_wR_factor_ref         0.1261
_refine_ls_goodness_of_fit_ref   0.7352

#_reflns_number_all 1732
_refine_ls_R_factor_all          0.1311
_refine_ls_wR_factor_all         0.1353

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                998
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_gt          0.1261

_refine_ls_shift/su_max          0.000103

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
16.5 21.9 7.11
;

_publ_section_abstract           
# Text of the abstract
# (a) The Abstract must be self-contained and comprehensible
# without the rest of the paper. This means no references
# to atom names or to compound numbers; compounds must be
# identified as the title compound, or by name or by some other
# means such as derivatives of each other (e.g. "the
# corresponding ketone").
# (b) The chemical formula of "the title compound" must be given.
# (c) Any crystallographic molecular symmetry should be
# mentioned, and also the presence of more than one molecule
# in the asymmetric unit (i.e. anything other than Z'=1).
;
?
;
_publ_section_comment            
# Text of the paper
# Note that atoms are referenced as N2, not N(2) or N~2~
# If text containing () occur within (), the outer ones should be []
# Figures should be referenced as Fih.
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    
# Captions to figures - Start each caption on a new line after a blank line
;
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50%
probability level. H atoms are shown as spheres of
arbitary radius.

;

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (Görbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
Å)
and
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
User-defined data collection reference

User defined data reduction

User defined cell refinement

Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.7083(5) -0.0894(5) 0.6919(3) 0.0458 1.0000 Uani . . . . . .
O1 O 0.7420(5) -0.5938(4) 0.5388(3) 0.0619 1.0000 Uani . . . . . .
O4 O 0.7216(5) -0.5991(4) 0.9503(3) 0.0538 1.0000 Uani . . . . . .
C5 C 0.7828(6) -0.0848(5) 0.8030(4) 0.0360 1.0000 Uani . . . . . .
O2 O 0.6129(6) -0.7171(4) 0.6642(3) 0.0724 1.0000 Uani . . . . . .
C3 C 0.7802(4) -0.4085(5) 0.8093(3) 0.0268 1.0000 Uani . . . . . .
C2 C 0.7150(4) -0.4124(5) 0.6919(3) 0.0275 1.0000 Uani . . . . . .
C1 C 0.6773(5) -0.2488(5) 0.6342(3) 0.0338 1.0000 Uani . . . . . .
C4 C 0.8194(5) -0.2399(5) 0.8631(4) 0.0370 1.0000 Uani . . . . . .
O3 O 0.9296(5) -0.6870(5) 0.8645(3) 0.0774 1.0000 Uani . . . . . .
C7 C 0.8178(5) -0.5816(5) 0.8786(3) 0.0341 1.0000 Uani . . . . . .
C6 C 0.6841(5) -0.5914(5) 0.6276(3) 0.0327 1.0000 Uani . . . . . .
H1 H 0.631(5) -0.246(6) 0.553(3) 0.042(11) 1.0000 Uiso . . . . . .
H2 H 0.869(6) -0.232(6) 0.939(4) 0.052(13) 1.0000 Uiso . . . . . .
H3 H 0.818(6) 0.012(6) 0.831(4) 0.046(12) 1.0000 Uiso . . . . . .
H5 H 0.678(7) 0.033(8) 0.649(5) 0.078(16) 1.0000 Uiso . . . . . .
H4 H 0.729(9) -0.744(11) 0.993(5) 0.13(3) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.059(2) 0.0242(17) 0.059(3) 0.010(2) 0.0230(19) 0.0064(17)
O1 0.115(3) 0.0337(15) 0.0495(19) -0.0125(14) 0.045(2) -0.0108(17)
O4 0.084(2) 0.0343(15) 0.054(2) 0.0155(14) 0.0374(17) 0.0078(15)
C5 0.050(2) 0.0151(17) 0.043(2) -0.0067(19) 0.0122(17) -0.0048(16)
O2 0.113(3) 0.0365(16) 0.087(3) -0.0255(17) 0.062(2) -0.0358(19)
C3 0.0295(18) 0.0192(15) 0.033(2) -0.0005(17) 0.0099(14) -0.0002(14)
C2 0.0299(18) 0.0243(16) 0.029(2) -0.0034(18) 0.0091(14) -0.0021(15)
C1 0.043(2) 0.0252(17) 0.0342(18) 0.0026(15) 0.0123(17) 0.0026(15)
C4 0.044(2) 0.0335(19) 0.0330(18) -0.0086(17) 0.0081(17) -0.0036(16)
O3 0.088(3) 0.060(2) 0.101(3) 0.046(2) 0.056(2) 0.043(2)
C7 0.042(2) 0.0271(17) 0.0335(19) 0.0030(17) 0.0090(16) 0.0029(16)
C6 0.0381(19) 0.0245(16) 0.0337(19) -0.0068(16) 0.0049(16) -0.0012(16)

_refine_ls_extinction_coef       54(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.539(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C5 . 1.337(5) yes
N1 . C1 . 1.354(5) yes
N1 . H5 . 1.04(6) no
O1 . H4 4_534 1.30(8) no
O1 . C6 . 1.265(4) yes
O4 . C7 . 1.281(4) yes
O4 . H4 . 1.18(8) no
C5 . C4 . 1.345(5) yes
C5 . H3 . 0.81(5) no
O2 . C6 . 1.211(4) yes
C3 . C2 . 1.399(4) yes
C3 . C4 . 1.397(5) yes
C3 . C7 . 1.512(5) yes
C2 . C1 . 1.384(5) yes
C2 . C6 . 1.516(5) yes
C1 . H1 . 0.97(4) no
C4 . H2 . 0.92(4) no
O3 . C7 . 1.201(5) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 . N1 . C1 . 121.8(4) yes
C5 . N1 . H5 . 119(3) no
C1 . N1 . H5 . 120(3) no
H4 4_534 O1 . C6 . 112(3) no
C7 . O4 . H4 . 115(3) no
N1 . C5 . C4 . 120.9(4) yes
N1 . C5 . H3 . 118(3) no
C4 . C5 . H3 . 120(3) no
C2 . C3 . C4 . 118.8(4) yes
C2 . C3 . C7 . 121.9(3) yes
C4 . C3 . C7 . 119.3(3) yes
C3 . C2 . C1 . 118.8(4) yes
C3 . C2 . C6 . 121.3(3) yes
C1 . C2 . C6 . 119.9(3) yes
C2 . C1 . N1 . 119.6(4) yes
C2 . C1 . H1 . 121(2) no
N1 . C1 . H1 . 119(2) no
C3 . C4 . C5 . 119.9(4) yes
C3 . C4 . H2 . 121(3) no
C5 . C4 . H2 . 119(3) no
C3 . C7 . O4 . 113.5(3) yes
C3 . C7 . O3 . 120.5(3) yes
O4 . C7 . O3 . 126.0(4) yes
C2 . C6 . O1 . 114.1(3) yes
C2 . C6 . O2 . 119.7(3) yes
O1 . C6 . O2 . 126.1(3) yes
O4 . H4 . O1 4_535 177(6) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H5 . O2 1_565 144 1.04 1.92 2.824(2) yes
O4 . H4 . O1 4_535 177 1.18 1.30 2.483(2) yes

# Attachment '34pdca_I_120K.cif'

data_CRYSTALS_cifIII
_database_code_depnum_ccdc_archive 'CCDC 686369'
_audit_creation_date             07-11-09
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title '120sad in P2(1)2(1)2(1)'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   5.2948(5)
_cell_length_b                   11.1107(11)
_cell_length_c                   11.1385(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     655.27(11)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            1

# Given Formula = C30 H22 N4 O8
# Dc = 1.44 Fooo = 344.00 Mu = 1.06 M = 141.63
# Found Formula = C28 H20 N4 O16
# Dc = 1.69 FOOO = 344.00 Mu = 1.42 M = 167.12

_chemical_formula_sum            'C28 H20 N4 O16'
_chemical_formula_moiety         'C28 H20 N4 O16'
_chemical_compound_source        ?
_chemical_formula_weight         668.48

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_max          ?

_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.142

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'DIFABS (Walker & Stuart, 1983)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  Unknown
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            5188
_reflns_number_total             1887
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections with Friedels Law is 1118
# Number of reflections without Friedels Law is 1887
# Theoretical number of reflections is about 955

_diffrn_reflns_theta_min         3.658
_diffrn_reflns_theta_max         29.993
_diffrn_measured_fraction_theta_max 0.981

_diffrn_reflns_theta_full        26.094
_diffrn_measured_fraction_theta_full 0.989

_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.29

_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_number_parameters     130

#_refine_ls_R_factor_ref 0.0303
_refine_ls_wR_factor_ref         0.0663
_refine_ls_goodness_of_fit_ref   0.8822

#_reflns_number_all 1885
_refine_ls_R_factor_all          0.0337
_refine_ls_wR_factor_all         0.0670

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1709
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0663

_refine_ls_shift/su_max          0.000246

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
2.77 3.53 1.16
;

_publ_section_abstract           
# Text of the abstract
# (a) The Abstract must be self-contained and comprehensible
# without the rest of the paper. This means no references
# to atom names or to compound numbers; compounds must be
# identified as the title compound, or by name or by some other
# means such as derivatives of each other (e.g. "the
# corresponding ketone").
# (b) The chemical formula of "the title compound" must be given.
# (c) Any crystallographic molecular symmetry should be
# mentioned, and also the presence of more than one molecule
# in the asymmetric unit (i.e. anything other than Z'=1).
;
?
;
_publ_section_comment            
# Text of the paper
# Note that atoms are referenced as N2, not N(2) or N~2~
# If text containing () occur within (), the outer ones should be []
# Figures should be referenced as Fih.
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    
# Captions to figures - Start each caption on a new line after a blank line
;
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50%
probability level. H atoms are shown as spheres of
arbitary radius.

;

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (Görbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
Å)
and
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
User-defined data collection reference

User defined data reduction

User defined cell refinement

Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Walker, N., & Stuart, (1983). D. Acta Cryst, A39, 158-166.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.03487(19) 0.15715(9) 0.64334(9) 0.0169 1.0000 Uani . . . . . .
N1 N 0.6740(2) 0.05308(11) 0.44822(10) 0.0167 1.0000 Uani . . . . . .
O4 O 0.5123(2) -0.18618(9) 0.81794(9) 0.0200 1.0000 Uani . . . . . .
O2 O 0.2238(2) 0.07111(10) 0.80207(9) 0.0206 1.0000 Uani . . . . . .
C2 C 0.3869(2) 0.03108(12) 0.60893(11) 0.0125 1.0000 Uani . . . . . .
C7 C 0.3797(2) -0.16468(11) 0.72820(11) 0.0134 1.0000 Uani . . . . . .
O3 O 0.1651(2) -0.20689(10) 0.70553(10) 0.0232 1.0000 Uani . . . . . .
C6 C 0.2037(2) 0.08845(11) 0.69489(12) 0.0135 1.0000 Uani . . . . . .
C3 C 0.4854(2) -0.08381(11) 0.63078(11) 0.0124 1.0000 Uani . . . . . .
C5 C 0.7736(3) -0.05590(13) 0.46798(12) 0.0173 1.0000 Uani . . . . . .
C4 C 0.6805(2) -0.12770(13) 0.55876(12) 0.0165 1.0000 Uani . . . . . .
C1 C 0.4831(3) 0.09764(11) 0.51433(11) 0.0157 1.0000 Uani . . . . . .
H1 H 0.426(4) 0.1782(17) 0.4967(16) 0.016(4) 1.0000 Uiso . . . . . .
H2 H 0.749(4) -0.2075(17) 0.5665(16) 0.021(5) 1.0000 Uiso . . . . . .
H3 H 0.910(3) -0.0765(16) 0.4188(16) 0.015(4) 1.0000 Uiso . . . . . .
H5 H 0.749(4) 0.0974(18) 0.3921(18) 0.023(5) 1.0000 Uiso . . . . . .
H4 H -0.027(6) 0.207(2) 0.700(2) 0.059(8) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0162(4) 0.0180(4) 0.0164(4) -0.0018(4) -0.0014(3) 0.0043(4)
N1 0.0170(5) 0.0189(6) 0.0143(5) -0.0016(4) 0.0029(4) -0.0061(4)
O4 0.0193(5) 0.0209(5) 0.0198(4) 0.0055(4) -0.0044(4) -0.0009(4)
O2 0.0234(5) 0.0232(5) 0.0152(5) 0.0031(4) 0.0035(4) 0.0079(4)
C2 0.0111(5) 0.0135(6) 0.0128(5) -0.0008(4) 0.0007(4) -0.0011(4)
C7 0.0156(5) 0.0109(5) 0.0139(5) -0.0004(4) 0.0011(4) 0.0003(4)
O3 0.0199(5) 0.0274(5) 0.0222(5) 0.0083(4) -0.0062(4) -0.0105(4)
C6 0.0128(5) 0.0121(5) 0.0156(6) 0.0004(4) 0.0024(4) 0.0004(4)
C3 0.0114(5) 0.0132(5) 0.0127(5) 0.0000(4) -0.0017(4) -0.0018(4)
C5 0.0131(5) 0.0222(6) 0.0165(6) -0.0043(5) 0.0030(4) -0.0024(5)
C4 0.0131(5) 0.0179(6) 0.0184(6) -0.0030(5) 0.0002(4) 0.0015(4)
C1 0.0179(6) 0.0140(6) 0.0153(5) -0.0002(4) 0.0009(5) -0.0020(5)

_refine_ls_extinction_coef       5(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.4031(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C6 . 1.3084(15) yes
O1 . H4 . 0.90(3) no
N1 . C5 . 1.3388(18) yes
N1 . C1 . 1.3452(17) yes
N1 . H5 . 0.89(2) no
O4 . C7 . 1.2445(16) yes
O2 . C6 . 1.2140(16) yes
C2 . C6 . 1.5045(18) yes
C2 . C3 . 1.4002(18) yes
C2 . C1 . 1.3844(17) yes
C7 . O3 . 1.2552(16) yes
C7 . C3 . 1.5157(17) yes
C3 . C4 . 1.3961(18) yes
C5 . C4 . 1.3790(19) yes
C5 . H3 . 0.935(18) no
C4 . H2 . 0.961(19) no
C1 . H1 . 0.965(19) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 . O1 . H4 . 107.5(19) no
C5 . N1 . C1 . 122.60(12) yes
C5 . N1 . H5 . 116.2(13) no
C1 . N1 . H5 . 121.0(13) no
C6 . C2 . C3 . 121.04(11) yes
C6 . C2 . C1 . 119.68(12) yes
C3 . C2 . C1 . 118.84(12) yes
O4 . C7 . O3 . 126.90(13) yes
O4 . C7 . C3 . 118.73(12) yes
O3 . C7 . C3 . 114.31(11) yes
C2 . C6 . O1 . 114.10(11) yes
C2 . C6 . O2 . 120.15(12) yes
O1 . C6 . O2 . 125.73(12) yes
C7 . C3 . C2 . 121.83(11) yes
C7 . C3 . C4 . 118.52(11) yes
C2 . C3 . C4 . 119.61(12) yes
N1 . C5 . C4 . 120.21(13) yes
N1 . C5 . H3 . 115.4(11) no
C4 . C5 . H3 . 124.4(11) no
C3 . C4 . C5 . 118.93(12) yes
C3 . C4 . H2 . 123.2(12) no
C5 . C4 . H2 . 117.8(12) no
C2 . C1 . N1 . 119.77(12) yes
C2 . C1 . H1 . 122.3(11) no
N1 . C1 . H1 . 117.8(11) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H5 . O4 4_654 160 0.89 1.80 2.655(2) yes
O1 . H4 . O3 3_556 174 0.90 1.60 2.497(2) yes

# Attachment '34pdca_I_400K.cif'

data_CRYSTALS_cifIV
_database_code_depnum_ccdc_archive 'CCDC 686370'
_audit_creation_date             07-11-09
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title '400sad in P2(1)2(1)2(1)'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   5.260(2)
_cell_length_b                   11.201(5)
_cell_length_c                   11.275(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     664.3(5)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            1

# Given Formula = C30 H22 N4 O8
# Dc = 1.42 Fooo = 344.00 Mu = 1.05 M = 141.63
# Found Formula = C28 H20 N4 O16
# Dc = 1.67 FOOO = 344.00 Mu = 1.40 M = 167.12

_chemical_formula_sum            'C28 H20 N4 O16'
_chemical_formula_moiety         'C28 H20 N4 O16'
_chemical_compound_source        ?
_chemical_formula_weight         668.48

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_max          ?

_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.140

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_diffrn_measurement_device_type  Unknown
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            5249
_reflns_number_total             1907
_diffrn_reflns_av_R_equivalents  0.031
# Number of reflections with Friedels Law is 1130
# Number of reflections without Friedels Law is 1907
# Theoretical number of reflections is about 965

_diffrn_reflns_theta_min         3.614
_diffrn_reflns_theta_max         29.986
_diffrn_measured_fraction_theta_max 0.978

_diffrn_reflns_theta_full        25.788
_diffrn_measured_fraction_theta_full 0.992

_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.19

_refine_ls_number_reflns         1390
_refine_ls_number_restraints     0
_refine_ls_number_parameters     130

#_refine_ls_R_factor_ref 0.0323
_refine_ls_wR_factor_ref         0.0643
_refine_ls_goodness_of_fit_ref   0.8776

#_reflns_number_all 1903
_refine_ls_R_factor_all          0.0423
_refine_ls_wR_factor_all         0.0660

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1390
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0643

_refine_ls_shift/su_max          0.000251

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
2.33 2.93 0.930
;

_publ_section_abstract           
# Text of the abstract
# (a) The Abstract must be self-contained and comprehensible
# without the rest of the paper. This means no references
# to atom names or to compound numbers; compounds must be
# identified as the title compound, or by name or by some other
# means such as derivatives of each other (e.g. "the
# corresponding ketone").
# (b) The chemical formula of "the title compound" must be given.
# (c) Any crystallographic molecular symmetry should be
# mentioned, and also the presence of more than one molecule
# in the asymmetric unit (i.e. anything other than Z'=1).
;
?
;
_publ_section_comment            
# Text of the paper
# Note that atoms are referenced as N2, not N(2) or N~2~
# If text containing () occur within (), the outer ones should be []
# Figures should be referenced as Fih.
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    
# Captions to figures - Start each caption on a new line after a blank line
;
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50%
probability level. H atoms are shown as spheres of
arbitary radius.

;

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (Görbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
Å)
and
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
User-defined data collection reference

User defined data reduction

User defined cell refinement

Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.2925(3) 0.39568(12) 0.40997(14) 0.0441 1.0000 Uani . . . . . .
O4 O 0.7521(3) 0.57122(13) 0.07222(13) 0.0486 1.0000 Uani . . . . . .
O2 O 0.4757(3) 0.55348(13) 0.32612(15) 0.0561 1.0000 Uani . . . . . .
C2 C 0.6396(3) 0.36293(15) 0.28329(15) 0.0292 1.0000 Uani . . . . . .
N1 N 0.9249(3) 0.20344(14) 0.30200(16) 0.0409 1.0000 Uani . . . . . .
C3 C 0.7318(3) 0.38397(13) 0.16945(15) 0.0282 1.0000 Uani . . . . . .
C7 C 0.6242(4) 0.48102(15) 0.09004(15) 0.0316 1.0000 Uani . . . . . .
O3 O 0.4175(3) 0.45603(15) 0.04509(16) 0.0603 1.0000 Uani . . . . . .
C6 C 0.4573(3) 0.44741(16) 0.34159(15) 0.0332 1.0000 Uani . . . . . .
C1 C 0.7388(4) 0.26957(16) 0.34751(17) 0.0375 1.0000 Uani . . . . . .
C4 C 0.9231(4) 0.31165(19) 0.12479(19) 0.0402 1.0000 Uani . . . . . .
C5 C 1.0181(4) 0.22253(18) 0.1936(2) 0.0431 1.0000 Uani . . . . . .
H1 H 0.664(4) 0.2500(19) 0.4254(18) 0.037(5) 1.0000 Uiso . . . . . .
H3 H 1.147(4) 0.174(2) 0.170(2) 0.047(6) 1.0000 Uiso . . . . . .
H2 H 0.993(5) 0.324(2) 0.046(2) 0.047(6) 1.0000 Uiso . . . . . .
H5 H 1.012(5) 0.145(3) 0.350(3) 0.073(8) 1.0000 Uiso . . . . . .
H4 H 0.213(7) 0.453(3) 0.461(3) 0.085(10) 1.0000 Uiso . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0446(8) 0.0391(7) 0.0486(8) -0.0041(6) 0.0162(7) -0.0024(6)
O4 0.0555(9) 0.0438(7) 0.0466(8) 0.0115(6) -0.0087(7) -0.0150(7)
O2 0.0690(10) 0.0331(8) 0.0663(10) 0.0115(7) 0.0287(8) 0.0130(7)
C2 0.0301(8) 0.0283(8) 0.0292(9) -0.0005(6) -0.0024(7) 0.0015(6)
N1 0.0435(10) 0.0319(8) 0.0473(10) -0.0021(7) -0.0145(8) 0.0088(7)
C3 0.0278(8) 0.0281(7) 0.0287(8) 0.0009(6) -0.0040(7) -0.0020(6)
C7 0.0362(9) 0.0330(9) 0.0256(8) 0.0017(7) -0.0006(7) 0.0001(7)
O3 0.0529(9) 0.0531(9) 0.0750(11) 0.0251(8) -0.0330(9) -0.0170(8)
C6 0.0365(9) 0.0346(9) 0.0285(8) 0.0013(7) 0.0009(7) 0.0066(8)
C1 0.0475(10) 0.0323(8) 0.0327(9) 0.0021(7) -0.0030(9) 0.0025(8)
C4 0.0374(10) 0.0449(11) 0.0383(10) -0.0045(8) 0.0079(8) 0.0035(8)
C5 0.0366(10) 0.0389(10) 0.0539(12) -0.0097(9) -0.0025(9) 0.0116(8)

_refine_ls_extinction_coef       12(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.4083(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C6 . 1.297(2) yes
O1 . H4 . 0.95(3) no
O4 . C7 . 1.230(2) yes
O2 . C6 . 1.205(2) yes
C2 . C3 . 1.392(2) yes
C2 . C6 . 1.499(2) yes
C2 . C1 . 1.375(2) yes
N1 . C1 . 1.330(3) yes
N1 . C5 . 1.334(3) yes
N1 . H5 . 0.97(3) no
C3 . C7 . 1.518(2) yes
C3 . C4 . 1.387(3) yes
C7 . O3 . 1.232(2) yes
C1 . H1 . 0.99(2) no
C4 . C5 . 1.360(3) yes
C4 . H2 . 0.97(2) no
C5 . H3 . 0.91(2) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 . O1 . H4 . 110.6(19) no
C3 . C2 . C6 . 121.36(15) yes
C3 . C2 . C1 . 118.81(16) yes
C6 . C2 . C1 . 119.47(16) yes
C1 . N1 . C5 . 122.32(18) yes
C1 . N1 . H5 . 120.8(17) no
C5 . N1 . H5 . 116.5(17) no
C2 . C3 . C7 . 122.35(15) yes
C2 . C3 . C4 . 119.27(17) yes
C7 . C3 . C4 . 118.35(16) yes
C3 . C7 . O4 . 118.72(16) yes
C3 . C7 . O3 . 114.15(16) yes
O4 . C7 . O3 . 127.02(18) yes
C2 . C6 . O1 . 113.97(16) yes
C2 . C6 . O2 . 120.53(17) yes
O1 . C6 . O2 . 125.47(17) yes
C2 . C1 . N1 . 119.98(18) yes
C2 . C1 . H1 . 119.1(13) no
N1 . C1 . H1 . 120.8(13) no
C3 . C4 . C5 . 119.23(18) yes
C3 . C4 . H2 . 121.8(14) no
C5 . C4 . H2 . 118.9(14) no
C4 . C5 . N1 . 120.36(19) yes
C4 . C5 . H3 . 123.4(15) no
N1 . C5 . H3 . 116.2(15) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H5 . O4 3_745 162 0.97 1.73 2.663(2) yes
O1 . H4 . O3 4_565 179 0.95 1.56 2.510(2) yes


