Electronic Supplementary MAterial for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'Marcel Bouvet'
;
Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite
Pierre et Marie Curie, CNRS-UMR 7071, 4 place Jussieu, case courrier 42
75252 Paris cedex 05, France.
;
B.
'Patrick Herson'
;
Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite
Pierre et Marie Curie, CNRS-UMR 7071, 4 place Jussieu, case courrier 42
75252 Pacris cedex 05, France.
;
P.
'Bernard Malezieux'
;
Laboratoire de Chimie Inorganique et Materiaux Moleculaires, Universite
Pierre et Marie Curie, CNRS-UMR 7071, 4 place Jussieu, case courrier 42
75252 Paris cedex 05, France.
;
O.
'Francoise Villain' Youchrett-Zallez
;
Laboratoire de Thermodynamique et d'Electrochimie, Departement de Chimie
Faculte des Sciences de Bizerte, 7021 Zarzouna, Bizerte, Tunisie.
;

_publ_contact_author_name        'Marcel Bouvet'
_publ_contact_author_address     
;
Chimie Inorganique et Materiaux Moleculaires
UPMC-CNRS
4, Place Jussieu
Paris
75252
FRANCE
;

_publ_contact_author_email       MARCEL.BOUVET@ESPCI.FR

_publ_section_title              
;
Self-Organization of the 2-Methoxyquinhydrone
Charge Transfer Complex in Polar Planes
;
_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_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_volume                  ?
_journal_year                    ?
_publ_contact_author_fax         '+33 1 44 27 38 41'

_publ_contact_author_phone       '+33 1 44 27 30 83'

# 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 have been
sent by mail.
;
_publ_requested_category         CO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    'Prof William Clegg'

# Attachment 'MB-cif1.doc'

data_1
_database_code_depnum_ccdc_archive 'CCDC 626640'
_audit_creation_date             06-01-26
_audit_creation_method           CRYSTALS_ver_12.82

_oxford_structure_analysis_title '1260941 Compound X'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.8386(10)
_cell_length_b                   12.791(3)
_cell_length_c                   13.187(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.170(11)
_cell_angle_gamma                90
_cell_volume                     1305.3(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-p 2ybc'
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'
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 = C14 H14 O6
# Dc = 1.42 Fooo = 584.00 Mu = 1.12 M = 278.26
# Found Formula = C14 H14 O6
# Dc = 1.42 FOOO = 584.00 Mu = 1.12 M = 278.26

_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_moiety         'C7 H8 O3, C7 H6 O3'
_chemical_compound_source        ?
_chemical_formula_weight         278.26

_cell_measurement_reflns_used    45
_cell_measurement_theta_min      5
_cell_measurement_theta_max      19.8
_cell_measurement_temperature    295

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.14

_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.112

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

_computing_data_collection       'COLLECT. Nonius (1997-2001).'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      295
_diffrn_reflns_number            11762
_reflns_number_total             3773
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections with Friedels Law is 3773
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3803

_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         30.003
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        28.503
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_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         0.33

_refine_ls_number_reflns         1213
_refine_ls_number_restraints     0
_refine_ls_number_parameters     183

#_refine_ls_R_factor_ref 0.0675
_refine_ls_wR_factor_ref         0.0570
_refine_ls_goodness_of_fit_ref   1.0526

#_reflns_number_all 3772
_refine_ls_R_factor_all          0.2296
_refine_ls_wR_factor_all         0.1282

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>1.50u(I)
_reflns_number_gt                1213
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_gt          0.0570

_refine_ls_shift/su_max          0.000121

# 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 F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refu
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.85 -0.490E-01 1.41
;

_publ_section_abstract           # Text of the abstract
; ?
;
_publ_section_comment            # Text of the paper
; ?
;
_publ_section_acknowledgements   # Acknowledgments
; ?
;
_publ_section_figure_captions    # Captions to figures
; ?
;

_publ_section_exptl_refinement   # Some potentially useful phrases are:
;
Because the data were collected with molybdenum radiation, there were no
measurable anomalous differences, as a consequence of which it was
admissible to merge Friedel pairs of reflections.

All hydrogen atoms were found in difference density syntheses.

Hydrogen atoms were placed geometrically after each cycle.

Hydrogen atoms were placed geometrically after each cycle, the preferred
orientations of those groups whose conformations could not be assigned
unambiguously having been previously identified by examination of a
difference Fourier map.

Hydrogen atoms were seen in a difference density synthesis. Those
attached to carbon atoms were repositioned geometrically.

Hydrogen were initially refined with soft restraints on the
bonds to regularise their geometry (bond lengths to accepted values,
angles either set by symmetry or to accepted values, and
U[iso] dependent upon the adjacent bonded atom),
after which they were refined with riding constraints only.

donated by Bill Clegg:

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
0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic
adps
(U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom),
after which they were refined with riding constraints.
.
;

_publ_section_exptl_prep         
; ?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

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

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G.M. (1986). SHELXS86. Program for the solution of
crystal structures. Univ. of G\"ottingen, Federal Republic of Germany.

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.
;

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
C1 C 0.6827(7) 0.2124(4) 0.8822(5) 0.0349 1.0000 Uani . . . . . .
C2 C 0.7385(7) 0.3232(4) 0.8667(4) 0.0261 1.0000 Uani . . . . . .
C3 C 0.8439(6) 0.3740(4) 0.9405(4) 0.0283 1.0000 Uani . . . . . .
C4 C 0.9056(7) 0.3233(4) 1.0399(5) 0.0308 1.0000 Uani . . . . . .
C5 C 0.8494(8) 0.2141(5) 1.0554(5) 0.0396 1.0000 Uani . . . . . .
C6 C 0.7422(7) 0.1638(4) 0.9819(5) 0.0358 1.0000 Uani . . . . . .
C7 C 0.7137(8) 0.4650(4) 0.7492(5) 0.0471 1.0000 Uani . . . . . .
C8 C 0.1705(7) 0.2104(4) 0.8913(4) 0.0265 1.0000 Uani . . . . . .
C9 C 0.2356(6) 0.1659(5) 0.9865(5) 0.0366 1.0000 Uani . . . . . .
C10 C 0.3556(7) 0.2169(4) 1.0582(5) 0.0318 1.0000 Uani . . . . . .
C11 C 0.4094(7) 0.3158(4) 1.0346(5) 0.0292 1.0000 Uani . . . . . .
C12 C 0.3471(7) 0.3638(4) 0.9406(5) 0.0308 1.0000 Uani . . . . . .
C13 C 0.2271(6) 0.3097(4) 0.8694(4) 0.0252 1.0000 Uani . . . . . .
C14 C 0.2102(7) 0.4527(4) 0.7488(4) 0.0312 1.0000 Uani . . . . . .
O1 O 0.5887(5) 0.1643(3) 0.8138(3) 0.0454 1.0000 Uani . . . . . .
O2 O 0.6694(4) 0.3585(3) 0.7723(3) 0.0356 1.0000 Uani . . . . . .
O3 O 1.0017(5) 0.3691(3) 1.1090(3) 0.0420 1.0000 Uani . . . . . .
O4 O 0.0499(5) 0.1561(3) 0.8247(3) 0.0399 1.0000 Uani . . . . . .
O5 O 0.1548(4) 0.3495(3) 0.7749(3) 0.0357 1.0000 Uani . . . . . .
O6 O 0.5291(5) 0.3726(3) 1.1016(3) 0.0444 1.0000 Uani . . . . . .
H4 H 0.0412 0.1787 0.7516 0.055(3) 1.0000 Uiso . . . . . .
H6 H 0.5796 0.3420 1.1614 0.055(3) 1.0000 Uiso . . . . . .
H31 H 0.8811 0.4470 0.9281 0.055(3) 1.0000 Uiso . . . . . .
H51 H 0.8922 0.1776 1.1216 0.055(3) 1.0000 Uiso . . . . . .
H61 H 0.7021 0.0917 0.9955 0.055(3) 1.0000 Uiso . . . . . .
H71 H 0.6564 0.4834 0.6782 0.055(3) 1.0000 Uiso . . . . . .
H72 H 0.6730 0.5137 0.7996 0.055(3) 1.0000 Uiso . . . . . .
H73 H 0.8417 0.4711 0.7537 0.055(3) 1.0000 Uiso . . . . . .
H91 H 0.1945 0.0949 1.0034 0.055(3) 1.0000 Uiso . . . . . .
H101 H 0.4021 0.1833 1.1255 0.055(3) 1.0000 Uiso . . . . . .
H121 H 0.3876 0.4352 0.9245 0.055(3) 1.0000 Uiso . . . . . .
H141 H 0.1492 0.4725 0.6790 0.055(3) 1.0000 Uiso . . . . . .
H142 H 0.3377 0.4523 0.7489 0.055(3) 1.0000 Uiso . . . . . .
H143 H 0.1817 0.5043 0.8005 0.055(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
C1 0.028(3) 0.043(3) 0.032(3) -0.013(3) -0.002(3) -0.003(2)
C2 0.031(2) 0.024(3) 0.024(3) 0.004(2) 0.007(2) 0.000(2)
C3 0.031(2) 0.034(3) 0.016(3) -0.003(2) -0.008(2) -0.005(2)
C4 0.029(3) 0.033(3) 0.031(3) -0.003(3) 0.007(3) -0.004(2)
C5 0.039(3) 0.043(4) 0.036(4) 0.005(3) 0.002(3) 0.002(3)
C6 0.043(3) 0.022(3) 0.041(4) 0.002(3) 0.003(3) -0.002(3)
C7 0.051(3) 0.039(4) 0.050(5) 0.008(3) 0.004(3) 0.002(3)
C8 0.029(3) 0.017(2) 0.034(3) 0.000(2) 0.006(3) -0.002(2)
C9 0.037(3) 0.035(4) 0.037(4) 0.004(3) 0.002(3) -0.004(3)
C10 0.036(3) 0.031(3) 0.024(3) 0.010(3) -0.008(3) 0.002(2)
C11 0.030(3) 0.036(3) 0.019(3) -0.006(2) -0.005(2) 0.005(2)
C12 0.031(3) 0.024(3) 0.040(4) -0.003(2) 0.013(3) -0.003(2)
C13 0.024(2) 0.028(3) 0.022(3) -0.005(2) -0.003(2) -0.001(2)
C14 0.039(3) 0.030(3) 0.024(3) 0.005(2) 0.003(2) 0.001(2)
O1 0.059(2) 0.032(2) 0.041(2) -0.0080(17) -0.0047(19) -0.0111(18)
O2 0.039(2) 0.040(2) 0.024(2) 0.0027(19) -0.0044(17) -0.0061(18)
O3 0.047(2) 0.043(2) 0.030(2) -0.0073(19) -0.0103(18) -0.0077(18)
O4 0.0484(19) 0.037(2) 0.030(2) -0.0049(16) -0.0054(16) -0.0182(17)
O5 0.041(2) 0.034(2) 0.029(2) 0.0013(18) -0.0046(18) -0.0023(17)
O6 0.048(2) 0.054(3) 0.026(2) -0.0003(19) -0.0084(18) -0.0070(19)

_refine_ls_extinction_coef       90
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 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
C1 . C2 . 1.507(8) yes
C1 . C6 . 1.461(9) yes
C1 . O1 . 1.234(7) yes
C2 . C3 . 1.341(7) yes
C2 . O2 . 1.353(7) yes
C3 . C4 . 1.472(8) yes
C3 . H31 . 1.000 no
C4 . C5 . 1.488(8) yes
C4 . O3 . 1.234(7) yes
C5 . C6 . 1.342(9) yes
C5 . H51 . 1.000 no
C6 . H61 . 1.000 no
C7 . O2 . 1.450(6) yes
C7 . H71 . 1.000 no
C7 . H72 . 1.000 no
C7 . H73 . 0.999 no
C8 . C9 . 1.399(8) yes
C8 . C13 . 1.392(7) yes
C8 . O4 . 1.372(7) yes
C9 . C10 . 1.386(9) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.385(8) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.399(8) yes
C11 . O6 . 1.387(7) yes
C12 . C13 . 1.401(8) yes
C12 . H121 . 1.001 no
C13 . O5 . 1.380(6) yes
C14 . O5 . 1.449(6) yes
C14 . H141 . 1.000 no
C14 . H142 . 1.000 no
C14 . H143 . 1.000 no
O4 . H4 . 0.998 no
O6 . H6 . 0.912 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
C2 . C1 . C6 . 117.7(5) yes
C2 . C1 . O1 . 121.4(6) yes
C6 . C1 . O1 . 120.9(6) yes
C1 . C2 . C3 . 121.0(6) yes
C1 . C2 . O2 . 110.9(5) yes
C3 . C2 . O2 . 128.1(5) yes
C2 . C3 . C4 . 120.7(5) yes
C2 . C3 . H31 . 119.7 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . C5 . 118.2(6) yes
C3 . C4 . O3 . 121.6(5) yes
C5 . C4 . O3 . 120.2(6) yes
C4 . C5 . C6 . 121.1(6) yes
C4 . C5 . H51 . 119.6 no
C6 . C5 . H51 . 119.4 no
C1 . C6 . C5 . 121.3(5) yes
C1 . C6 . H61 . 119.3 no
C5 . C6 . H61 . 119.4 no
O2 . C7 . H71 . 109.3 no
O2 . C7 . H72 . 109.4 no
H71 . C7 . H72 . 109.5 no
O2 . C7 . H73 . 109.5 no
H71 . C7 . H73 . 109.6 no
H72 . C7 . H73 . 109.6 no
C9 . C8 . C13 . 118.4(5) yes
C9 . C8 . O4 . 119.0(5) yes
C13 . C8 . O4 . 122.6(5) yes
C8 . C9 . C10 . 122.1(5) yes
C8 . C9 . H91 . 119.0 no
C10 . C9 . H91 . 118.9 no
C9 . C10 . C11 . 118.3(5) yes
C9 . C10 . H101 . 120.9 no
C11 . C10 . H101 . 120.7 no
C10 . C11 . C12 . 121.6(5) yes
C10 . C11 . O6 . 122.3(5) yes
C12 . C11 . O6 . 116.1(5) yes
C11 . C12 . C13 . 118.7(5) yes
C11 . C12 . H121 . 120.7 no
C13 . C12 . H121 . 120.6 no
C12 . C13 . C8 . 120.9(6) yes
C12 . C13 . O5 . 124.0(5) yes
C8 . C13 . O5 . 115.1(5) yes
O5 . C14 . H141 . 109.4 no
O5 . C14 . H142 . 109.5 no
H141 . C14 . H142 . 109.5 no
O5 . C14 . H143 . 109.4 no
H141 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no
C7 . O2 . C2 . 115.7(4) yes
C8 . O4 . H4 . 113.9 no
C14 . O5 . C13 . 117.0(4) yes
C11 . O6 . H6 . 118.8 no

# Attachment 'MB-cif2.doc'

data_2
_database_code_depnum_ccdc_archive 'CCDC 626643'
_audit_creation_date             06-10-23
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title '10230942 Compound X'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   4.9678(7)
_cell_length_b                   10.533(4)
_cell_length_c                   13.094(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.194(13)
_cell_angle_gamma                90
_cell_volume                     685.0(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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'
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 H8 O3
# Dc = 1.36 Fooo = 296.00 Mu = 1.07 M = 140.14
# Found Formula = C7 H8 O3
# Dc = 1.36 FOOO = 296.00 Mu = 1.07 M = 140.14

_chemical_formula_sum            'C7 H8 O3'
_chemical_formula_moiety         'C7 H8 O3'
_chemical_compound_source        ?
_chemical_formula_weight         140.14

_cell_measurement_reflns_used    35
_cell_measurement_theta_min      3
_cell_measurement_theta_max      22
_cell_measurement_temperature    295

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.107

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      295
_diffrn_reflns_number            3578
_reflns_number_total             1564
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections with Friedels Law is 1564
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1574

_diffrn_reflns_theta_min         3.665
_diffrn_reflns_theta_max         27.505
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        26.679
_diffrn_measured_fraction_theta_full 0.993

_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_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         -0.28
_refine_diff_density_max         0.25

_refine_ls_number_reflns         978
_refine_ls_number_restraints     0
_refine_ls_number_parameters     93

#_refine_ls_R_factor_ref 0.0473
_refine_ls_wR_factor_ref         0.0595
_refine_ls_goodness_of_fit_ref   1.0549

#_reflns_number_all 1564
_refine_ls_R_factor_all          0.0706
_refine_ls_wR_factor_all         0.0756

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.0\s(I)
_reflns_number_gt                978
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_gt          0.0595

_refine_ls_shift/su_max          0.000562

# 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 F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refu
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.71 0.783 1.20
;

_publ_section_abstract           
# Text of the 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 (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

G\"orbitz, 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
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ 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         
;
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.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

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

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G.M. (1986). SHELXS86. Program for the solution of
crystal structures. Univ. of G\"ottingen, Federal Republic of Germany.

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.
;

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
C1 C 0.5213(3) 0.18888(18) 0.83841(13) 0.0330 1.0000 Uani . . . . . .
C2 C 0.5188(4) 0.2276(2) 0.94060(14) 0.0377 1.0000 Uani . . . . . .
C3 C 0.3345(4) 0.3187(2) 0.97086(13) 0.0382 1.0000 Uani . . . . . .
C4 C 0.1492(4) 0.3708(2) 0.90171(15) 0.0416 1.0000 Uani . . . . . .
C5 C 0.1543(4) 0.3324(2) 0.79941(14) 0.0390 1.0000 Uani . . . . . .
C6 C 0.3379(4) 0.24378(18) 0.76718(13) 0.0345 1.0000 Uani . . . . . .
C7 C 0.8640(4) 0.0317(2) 0.86903(18) 0.0522 1.0000 Uani . . . . . .
O1 O 0.6905(3) 0.09955(14) 0.79896(10) 0.0452 1.0000 Uani . . . . . .
O2 O 0.3245(3) 0.35967(17) 1.07213(10) 0.0538 1.0000 Uani . . . . . .
O3 O 0.3345(3) 0.20655(16) 0.66538(10) 0.0488 1.0000 Uani . . . . . .
H2 H 0.6600 0.1863 0.9861 0.069(3) 1.0000 Uiso . . . . . .
H4 H 0.0006 0.4228 0.9289 0.069(3) 1.0000 Uiso . . . . . .
H5 H 0.0225 0.3678 0.7527 0.069(3) 1.0000 Uiso . . . . . .
H6 H 0.4944 0.3434 1.1011 0.069(3) 1.0000 Uiso . . . . . .
H7 H 0.4988 0.1794 0.6509 0.069(3) 1.0000 Uiso . . . . . .
H72 H 0.9869 0.0913 0.9045 0.069(3) 1.0000 Uiso . . . . . .
H73 H 0.9700 -0.0300 0.8277 0.069(3) 1.0000 Uiso . . . . . .
H71 H 0.7513 -0.0137 0.9214 0.069(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
C1 0.0259(8) 0.0415(10) 0.0314(8) 0.0017(7) -0.0018(6) -0.0010(7)
C2 0.0301(9) 0.0527(11) 0.0300(9) 0.0036(7) -0.0062(7) 0.0007(7)
C3 0.0333(9) 0.0540(11) 0.0273(8) -0.0018(8) 0.0006(6) -0.0038(8)
C4 0.0365(10) 0.0493(12) 0.0390(10) -0.0013(8) 0.0014(7) 0.0047(8)
C5 0.0350(10) 0.0475(11) 0.0341(9) 0.0046(8) -0.0072(7) 0.0045(8)
C6 0.0331(9) 0.0446(10) 0.0256(8) 0.0013(7) -0.0037(7) -0.0042(7)
C7 0.0433(11) 0.0530(12) 0.0600(13) 0.0026(11) -0.0062(9) 0.0121(10)
O1 0.0421(8) 0.0565(9) 0.0367(7) -0.0058(6) -0.0056(5) 0.0117(6)
O2 0.0452(8) 0.0865(13) 0.0295(7) -0.0133(7) -0.0013(5) 0.0049(7)
O3 0.0443(8) 0.0763(11) 0.0256(7) -0.0058(7) -0.0074(5) 0.0080(7)

_refine_ls_extinction_coef       110
_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
C1 . C2 . 1.399(3) yes
C1 . C6 . 1.414(2) yes
C1 . O1 . 1.370(2) yes
C2 . C3 . 1.390(3) yes
C2 . H2 . 1.010 no
C3 . C4 . 1.391(3) yes
C3 . O2 . 1.396(2) yes
C4 . C5 . 1.400(3) yes
C4 . H4 . 0.991 no
C5 . C6 . 1.377(3) yes
C5 . H5 . 0.962 no
C6 . O3 . 1.389(2) yes
C7 . O1 . 1.436(2) yes
C7 . H72 . 0.985 no
C7 . H73 . 1.002 no
C7 . H71 . 1.014 no
O2 . H6 . 0.934 no
O3 . H7 . 0.889 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
C2 . C1 . C6 . 119.56(17) yes
C2 . C1 . O1 . 125.34(15) yes
C6 . C1 . O1 . 115.10(15) yes
C1 . C2 . C3 . 119.53(16) yes
C1 . C2 . H2 . 114.8 no
C3 . C2 . H2 . 125.7 no
C2 . C3 . C4 . 121.20(17) yes
C2 . C3 . O2 . 121.39(17) yes
C4 . C3 . O2 . 117.40(18) yes
C3 . C4 . C5 . 118.94(17) yes
C3 . C4 . H4 . 118.2 no
C5 . C4 . H4 . 122.1 no
C4 . C5 . C6 . 120.96(16) yes
C4 . C5 . H5 . 118.0 no
C6 . C5 . H5 . 121.0 no
C1 . C6 . C5 . 119.78(16) yes
C1 . C6 . O3 . 120.82(17) yes
C5 . C6 . O3 . 119.37(16) yes
O1 . C7 . H72 . 110.0 no
O1 . C7 . H73 . 107.0 no
H72 . C7 . H73 . 109.9 no
O1 . C7 . H71 . 109.5 no
H72 . C7 . H71 . 109.1 no
H73 . C7 . H71 . 111.2 no
C7 . O1 . C1 . 117.75(14) yes
C3 . O2 . H6 . 106.2 no
C6 . O3 . H7 . 107.6 no


