
###########################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
###########################################################################
#
#  This CIF contains data generated directly from one or more entries in
#  the Cambridge Structural Database and will include bibliographic, 
#  chemical, crystal, experimental, refinement, and atomic coordinate data,
#  as available.
#     
#  Copyright  2013  The Cambridge Crystallographic Data Centre
# 
#  This CIF is provided on the understanding that it is used for bona fide 
#  research purposes only.  It may contain copyright material of the CCDC
#  or of third parties, and may not be copied or further disseminated in 
#  any form, whether machine-readable or not, except for the purpose of 
#  generating routine backup copies on your local computer system.
# 
#  For further information about the CCDC, data deposition and data 
#  retrieval see <www.ccdc.cam.ac.uk>. Bona fide researchers may freely 
#  download  Mercury and enCIFer from this site to visualise CIF-encoded 
#  structures and to carry out CIF format checking respectively.
#
###########################################################################

data_CSD_CIF_HXDYOM
_audit_creation_date 1978-11-29
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD HXDYOM
_chemical_formula_sum 'C6 H6 O1'
_chemical_formula_moiety
;
C6 H6 O1
;
_journal_coeditor_code "IUCr A16282"
_journal_coden_Cambridge 107
_journal_volume 34
_journal_year 1978
_journal_page_first 2365
_journal_name_full 'Acta Crystallogr.,Sect.B:Struct.Crystallogr.Cryst.Chem. '
loop_
_publ_author_name
"D.A.Fisher"
"D.N.Batchelder"
"M.B.Hursthouse"
_chemical_name_systematic
;
2,4-Hexadiyn-1-ol
;
_cell_volume    539.548
_diffrn_ambient_temperature 110
#These two values have been output from a single CSD field.
_refine_ls_R_factor_gt 0.13
_refine_ls_wR_factor_gt 0.13
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/a'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,-z
3 -x,-y,-z
4 -1/2+x,-1/2-y,z
_cell_length_a 4.875(2)
_cell_length_b 28.117(18)
_cell_length_c 4.028(1)
_cell_angle_alpha 90
_cell_angle_beta 102.25(4)
_cell_angle_gamma 90
_cell_formula_units_Z 4
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.23
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C -0.27390 0.18590 0.06700
C2 C -0.05510 0.15350 0.23470
C3 C 0.13040 0.12740 0.36820
C4 C 0.33880 0.09710 0.52440
C5 C 0.52340 0.07100 0.66320
C6 C 0.74940 0.03950 0.82890
O1 O -0.28370 0.22890 0.25350
H1 H -0.47600 0.16800 0.10300
H2 H -0.23900 0.20000 -0.20700
H3 H 0.72600 0.03900 1.10200
H4 H 0.97200 0.05400 0.80900
H5 H 0.77800 0.03800 0.55800
H6 H -0.04200 0.24500 0.26700
#END

data_CSD_CIF_PHENOL01
_audit_creation_date 1971-12-31
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD PHENOL01
_chemical_formula_sum 'C6 H6 O1'
_chemical_formula_moiety
;
C6 H6 O1
;
_journal_coden_Cambridge 25
_journal_year 1967
_journal_page_first 1988
_journal_name_full 'Bull.Soc.Chim.Fr. '
loop_
_publ_author_name
"H.Gillier-Pandraud"
_chemical_name_systematic
;
Phenol
;
_cell_volume    826.108
_exptl_crystal_density_diffrn 1.13
_exptl_special_details
;
ambient-pressure polymorph

;
_diffrn_ambient_temperature ?
_diffrn_special_details
;
The study was carried out at room temperature,in the range 283-303K

;
#These two values have been output from a single CSD field.
_refine_ls_R_factor_gt 0.15
_refine_ls_wR_factor_gt 0.15
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 2 21'
_symmetry_Int_Tables_number 18
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2+x,-y,-z
3 -x,y,1/2-z
4 1/2-x,-y,1/2+z
_cell_length_a 6.02(2)
_cell_length_b 9.04(3)
_cell_length_c 15.18(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 6
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.00000 -0.21680 0.25000
C2 C 0.34310 0.38610 0.11610
C3 C 0.18260 -0.14830 0.21700
C4 C 0.15360 0.39390 0.06200
C5 C 0.18210 0.01060 0.21550
C6 C 0.15600 0.29120 -0.01080
C7 C 0.00000 0.08320 0.25000
C8 C 0.33330 0.19430 -0.02410
C9 C 0.52010 0.19920 0.02850
C10 C 0.52720 0.29780 0.10340
O1 O 0.00000 -0.37280 0.25000
O2 O 0.35590 0.47730 0.18760
C5B C -0.18210 0.01060 0.28450
C3B C -0.18260 -0.14830 0.28300
#END

data_CSD_CIF_PHENOL02
_audit_creation_date 1971-12-31
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD PHENOL02
_chemical_formula_sum 'C6 H6 O1'
_chemical_formula_moiety
;
C6 H6 O1
;
_journal_coden_Cambridge 25
_journal_year 1967
_journal_page_first 1988
_journal_name_full 'Bull.Soc.Chim.Fr. '
loop_
_publ_author_name
"H.Gillier-Pandraud"
_chemical_name_systematic
;
Phenol
;
_cell_volume    826.108
_exptl_crystal_density_diffrn 1.13
_exptl_special_details
;
ambient-pressure polymorph
Crystal structure is pseudo-orthorhombic P21221 with z'=1.5
;
_diffrn_ambient_temperature ?
_diffrn_special_details
;
The study was carried out at room temperature,in the range 283-303K

;
#These two values have been output from a single CSD field.
_refine_ls_R_factor_gt 0.14
_refine_ls_wR_factor_gt 0.14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 1 1 21'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
_cell_length_a 6.02(2)
_cell_length_b 9.04(3)
_cell_length_c 15.18(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 6
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.00170 -0.21760 0.25480
C2 C 0.33880 0.38530 0.12210
C3 C -0.33690 0.38590 0.38940
C4 C 0.18260 -0.14760 0.22220
C5 C 0.15640 0.39450 0.06790
C6 C -0.15440 0.39510 0.44260
C7 C 0.17840 0.00920 0.22180
C8 C 0.15710 0.28800 -0.00560
C9 C -0.15870 0.28900 0.51740
C10 C 0.01050 0.08490 0.25320
C11 C 0.32560 0.19560 -0.01900
C12 C -0.33120 0.19520 0.52820
C13 C -0.18220 0.01180 0.28700
C14 C 0.51620 0.20060 0.03350
C15 C -0.51200 0.19910 0.47690
C16 C -0.18280 -0.14730 0.28660
C17 C 0.53180 0.29750 0.10870
C18 C -0.51930 0.29760 0.40410
O1 O 0.00220 -0.37350 0.25460
O2 O 0.35200 0.47810 0.19130
O3 O -0.35000 0.47550 0.31790
#END

data_CSD_CIF_PHENOL03
_audit_creation_date 1989-10-10
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD PHENOL03
_chemical_formula_sum 'C6 H6 O1'
_chemical_formula_moiety
;
C6 H6 O1
;
_journal_coden_Cambridge 82
_journal_volume 28
_journal_year 1987
_journal_page_first 175-5
_journal_name_full 'Zh.Strukt.Khim.(Russ.)(J.Struct.Chem.) '
loop_
_publ_author_name
"V.E.Zavodnik"
"V.K.Bel'skii"
"P.M.Zorkii"
_chemical_name_systematic
;
Phenol
;
_cell_volume    788.006
_exptl_crystal_density_diffrn 1.19
_exptl_special_details
;
ambient-pressure polymorph
Crystal structure is pseudo-orthorhombic P21221 with z'=1.5
;
_diffrn_ambient_temperature 123
#These two values have been output from a single CSD field.
_refine_ls_R_factor_gt 0.04
_refine_ls_wR_factor_gt 0.04
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 1 1 21'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
_cell_length_a 6.050(1)
_cell_length_b 8.925(2)
_cell_length_c 14.594(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90.36(2)
_cell_formula_units_Z 6
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.23
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O1 O 0.8467(3) 0.5161(2) 0.25000
O2 O 0.5509(3) 0.4999(2) 0.3849(2)
O3 O 0.1932(3) 0.6505(2) 0.3265(2)
C1 C 0.8848(4) 0.4102(3) 0.1834(2)
C2 C 0.5886(4) 0.3961(3) 0.4526(2)
C3 C 0.2217(4) 0.8023(2) 0.3261(2)
C4 C 1.0825(5) 0.4048(3) 0.1366(2)
C5 C 0.7887(4) 0.3190(3) 0.4567(2)
C6 C 0.0468(4) 0.8900(3) 0.2954(2)
C7 C 1.1130(6) 0.2959(4) 0.0698(2)
C8 C 0.8198(6) 0.2127(3) 0.5249(3)
C9 C 0.0694(4) 1.0450(3) 0.2937(2)
C10 C 0.9429(7) 0.1936(4) 0.0504(2)
C11 C 0.6561(7) 0.1848(4) 0.5885(2)
C12 C 0.2624(5) 1.1125(3) 0.3233(2)
C13 C 0.7460(6) 0.2018(3) 0.0967(2)
C14 C 0.4595(7) 0.2640(4) 0.5845(2)
C15 C 0.4367(4) 1.0241(3) 0.3540(2)
C16 C 0.7131(5) 0.3101(3) 0.1636(2)
C17 C 0.4254(5) 0.3706(3) 0.5170(2)
C18 C 0.4182(4) 0.8698(3) 0.3556(2)
H1 H 0.9665(50) 0.5570(34) 0.2581(26)
H2 H 0.6757(44) 0.5123(32) 0.3514(23)
H3 H 0.2998(59) 0.6239(36) 0.3444(24)
H4 H 1.2010(63) 0.4695(46) 0.1472(35)
H5 H 0.9132(62) 0.3376(44) 0.4183(34)
H6 H -0.0950(52) 0.8444(41) 0.2809(31)
H7 H 1.2568(75) 0.3008(61) 0.0403(40)
H8 H 0.9579(72) 0.1767(50) 0.5280(38)
H9 H -0.0488(61) 1.1008(42) 0.2633(34)
H10 H 0.9776(90) 0.1242(53) -0.0019(34)
H11 H 0.6625(90) 0.1095(56) 0.6383(35)
H12 H 0.2875(70) 1.2289(38) 0.3241(28)
H13 H 0.6226(81) 0.1477(47) 0.086(4)
H14 H 0.3263(90) 0.2578(63) 0.6227(38)
H15 H 0.5691(56) 1.0658(42) 0.3727(41)
H16 H 0.5606(51) 0.3176(45) 0.1985(34)
H17 H 0.3031(63) 0.4194(49) 0.5128(31)
H18 H 0.5407(53) 0.8116(38) 0.3754(32)
#END

data_CSD_CIF_PHENOL10
_audit_creation_date 1971-12-31
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD PHENOL10
_chemical_formula_sum 'C6 H6 O1'
_chemical_formula_moiety
;
C6 H6 O1
;
_journal_coden_Cambridge 5
_journal_volume 119
_journal_year 1963
_journal_page_first 273
_journal_name_full 'Z.Kristallogr.,Kristallgeom.,Kristallphys.,Kristallchem. '
loop_
_publ_author_name
"C.Scheringer"
_chemical_name_systematic
;
Phenol
;
_cell_volume    811.323
_exptl_special_details
;
ambient-pressure polymorph
Crystal structure is pseudo-orthorhombic P21221 with z'=1.5
;
_diffrn_ambient_temperature ?
_diffrn_special_details
;
The study was carried out at room temperature,in the range 283-303K

;
#These two values have been output from a single CSD field.
_refine_ls_R_factor_gt 0.207
_refine_ls_wR_factor_gt 0.207
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 1 1 21'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
_cell_length_a 5.97
_cell_length_b 9.0
_cell_length_c 15.1
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 6
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.20
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C1 C 0.25500 -0.21300 0.25000
C2 C 0.10000 0.28500 -0.00900
C3 C -0.27600 0.29900 0.10200
C4 C -0.27500 0.20300 0.03100
C5 C -0.40400 0.38900 0.38500
C6 C -0.42700 0.20100 0.52700
C7 C -0.22600 0.29300 0.40100
C8 C -0.23700 0.19900 0.47300
C9 C -0.59400 0.39100 0.43900
C10 C -0.60500 0.29700 0.51100
C11 C 0.24800 0.08900 0.25000
C12 C 0.06500 -0.14000 0.21800
C13 C 0.06200 0.01100 0.21800
C14 C 0.44100 -0.13600 0.28200
C15 C 0.43700 0.01500 0.28100
C16 C -0.08900 0.38800 0.11700
C17 C -0.08700 0.19600 -0.02400
C18 C 0.09900 0.38100 0.06100
H1 H -0.41800 0.30500 0.14400
H2 H -0.41700 0.13500 0.02000
H3 H -0.43500 0.12900 0.58200
H4 H -0.08300 0.29300 0.35900
H5 H -0.10300 0.12600 0.48600
H6 H -0.72800 0.46400 0.42600
H7 H -0.74800 0.29800 0.55200
H8 H 0.24500 0.20500 0.24900
H9 H -0.07500 -0.19900 0.19400
H10 H -0.08100 0.06800 0.19400
H11 H 0.58300 -0.19300 0.30600
H12 H 0.57800 0.07500 0.30500
H13 H -0.08700 0.12200 -0.07800
H14 H 0.24000 0.44900 0.07300
H15 H 0.24100 0.27900 -0.05100
O1 O 0.25800 -0.36600 0.25000
O2 O -0.09000 0.48600 0.18800
O3 O -0.39300 0.48400 0.31200
#END

data_CSD_CIF_PHENOL11
_audit_creation_date 2003-02-20
_audit_creation_method CSD-ConQuest-V1
_database_code_CSD PHENOL11
_database_code_depnum_ccdc_archive 'CCDC 201623'
_chemical_formula_sum 'C6 H6 O1'
_chemical_formula_moiety
;
C6 H6 O1
;
_journal_coeditor_code "IUCr BM0050"
_journal_coden_Cambridge 622
_journal_volume 58
_journal_year 2002
_journal_page_first 1018
_journal_name_full 'Acta Crystallogr.,Sect.B:Struct.Sci. '
loop_
_publ_author_name
"D.R.Allan"
"S.J.Clark"
"A.Dawson"
"P.A.McGregor"
"S.Parsons"
_chemical_name_systematic
;
Phenol
;
_chemical_melting_point 313
_cell_volume    756.419
_exptl_crystal_colour 'colorless'
_exptl_crystal_density_diffrn 1.24
_exptl_special_details
;
high-pressure polymorph

;
_exptl_crystal_description 'cylindrical'
_diffrn_ambient_temperature 293
_diffrn_ambient_pressure 160000.0
#These two values have been output from a single CSD field.
_refine_ls_R_factor_gt 0.0863
_refine_ls_wR_factor_gt 0.0863
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_Int_Tables_number 4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
_cell_length_a 11.610(4)
_cell_length_b 5.4416(11)
_cell_length_c 12.217(5)
_cell_angle_alpha 90
_cell_angle_beta 101.47(3)
_cell_angle_gamma 90
_cell_formula_units_Z 6
loop_
_atom_type_symbol
_atom_type_radius_bond
C 0.68
H 0.23
O 0.68
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O1 O 0.705(1) 0.4386(19) 0.3000(15)
H1 H 0.67160 0.32300 0.32350
C1 C 0.6911(8) 0.4219(16) 0.1876(15)
C2 C 0.6275(9) 0.2301(18) 0.1293(17)
H2 H 0.59350 0.11130 0.16750
C3 C 0.6146(10) 0.216(2) 0.0139(17)
H3 H 0.57210 0.08770 -0.02510
C4 C 0.6654(11) 0.394(3) -0.0432(15)
H4 H 0.65680 0.38420 -0.12040
C5 C 0.7290(11) 0.585(3) 0.0150(15)
H5 H 0.76290 0.70430 -0.02320
C6 C 0.7418(9) 0.5996(18) 0.1304(15)
H6 H 0.78440 0.72790 0.16940
O2 O 0.6823(10) 0.937(2) 0.3864(14)
H7 H 0.72090 0.81930 0.37200
C7 C 0.6694(11) 0.923(2) 0.4937(14)
C8 C 0.7169(10) 0.726(2) 0.5603(15)
H8 H 0.75970 0.60590 0.53170
C9 C 0.7005(9) 0.709(3) 0.6697(15)
H9 H 0.73220 0.57760 0.71430
C10 C 0.6366(10) 0.889(3) 0.7124(14)
H10 H 0.62560 0.87730 0.78560
C11 C 0.5891(9) 1.085(3) 0.6458(14)
H11 H 0.54630 1.20530 0.67440
C12 C 0.6055(10) 1.102(2) 0.5364(14)
H12 H 0.57370 1.23370 0.49180
O3 O 1.0164(12) 0.860(2) 0.4541(16)
H13 H 0.98180 0.97140 0.47910
C13 C 1.0088(13) 0.893(2) 0.3444(13)
C14 C 0.9567(10) 1.0874(15) 0.2791(17)
H14 H 0.91670 1.20840 0.31030
C15 C 0.9644(10) 1.101(2) 0.1671(16)
H15 H 0.92950 1.23140 0.12350
C16 C 1.0241(12) 0.920(4) 0.1205(13)
H16 H 1.02930 0.92950 0.04560
C17 C 1.0762(10) 0.726(3) 0.1858(17)
H17 H 1.11620 0.60460 0.15460
C18 C 1.0686(11) 0.7119(15) 0.2977(16)
H18 H 1.10340 0.58170 0.34140
#END
