#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:56:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180523 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/92/7219239.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219239
loop_
_publ_author_name
'Batisai, Eustina'
'Smith, Vincent J.'
'Bourne, Susan A.'
'Báthori, Nikoletta B.'
_publ_section_title
;
 Solid state structures of p-cresol revisited
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              5134
_journal_paper_doi               10.1039/C4CE02334J
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13
_chemical_name_systematic        p-cresol
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-07 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.8320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.6775(3)
_cell_length_b                   11.7141(7)
_cell_length_c                   18.3172(11)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.07
_cell_volume                     1203.77(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8636
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0561P)²+0.8939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                2143
_reflns_number_total             2479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce02334j2.cif
_cod_data_source_block           formI
_cod_depositor_comments
'Adding full bibliography for 7219239--7219240.cif.'
_cod_original_sg_symbol_H-M      p21/n
_cod_database_code               7219239
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O9 O -0.0158(3) 0.48678(12) 0.60543(7) 0.0442(4) Uani 1 1 d .
H9 H -0.1280 0.4464 0.5710 0.053 Uiso 1 1 calc R
C13 C 0.4633(3) 0.25940(15) 0.72554(9) 0.0328(4) Uani 1 1 d .
C10 C 0.1389(3) 0.41015(15) 0.64520(9) 0.0322(4) Uani 1 1 d .
C3 C 0.5534(4) 0.73100(17) 0.50035(10) 0.0426(5) Uani 1 1 d .
H3 H 0.5877 0.6815 0.4623 0.051 Uiso 1 1 calc R
C14 C 0.5175(3) 0.37454(16) 0.71909(10) 0.0380(4) Uani 1 1 d .
H14 H 0.6677 0.4022 0.7424 0.046 Uiso 1 1 calc R
C12 C 0.2416(3) 0.22218(15) 0.69068(10) 0.0359(4) Uani 1 1 d .
H12 H 0.2001 0.1440 0.6943 0.043 Uiso 1 1 calc R
C5 C 0.6433(3) 0.90263(15) 0.57287(9) 0.0346(4) Uani 1 1 d .
C4 C 0.6883(3) 0.82805(17) 0.51786(10) 0.0407(4) Uani 1 1 d .
H4 H 0.8158 0.8442 0.4914 0.049 Uiso 1 1 calc R
C11 C 0.0792(3) 0.29619(15) 0.65079(10) 0.0354(4) Uani 1 1 d .
H11 H -0.0713 0.2689 0.6276 0.042 Uiso 1 1 calc R
C15 C 0.3582(3) 0.44965(16) 0.67963(10) 0.0379(4) Uani 1 1 d .
H15 H 0.3990 0.5279 0.6761 0.045 Uiso 1 1 calc R
C2 C 0.3693(3) 0.70666(17) 0.53847(10) 0.0414(5) Uani 1 1 d .
C6 C 0.4563(3) 0.87601(17) 0.61049(10) 0.0393(4) Uani 1 1 d .
H6 H 0.4213 0.9255 0.6485 0.047 Uiso 1 1 calc R
C7 C 0.3191(3) 0.77848(19) 0.59373(10) 0.0442(5) Uani 1 1 d .
H7 H 0.1919 0.7615 0.6201 0.053 Uiso 1 1 calc R
C16 C 0.6388(4) 0.17870(18) 0.76865(11) 0.0430(5) Uani 1 1 d .
H16A H 0.7836 0.2206 0.7889 0.065 Uiso 0.50 1 calc PR
H16B H 0.6792 0.1179 0.7359 0.065 Uiso 0.50 1 calc PR
H16C H 0.5677 0.1451 0.8092 0.065 Uiso 0.50 1 calc PR
H16D H 0.5701 0.1018 0.7671 0.065 Uiso 0.50 1 calc PR
H16E H 0.6745 0.2044 0.8201 0.065 Uiso 0.50 1 calc PR
H16F H 0.7859 0.1773 0.7468 0.065 Uiso 0.50 1 calc PR
C8 C 0.7922(4) 1.00840(18) 0.59045(12) 0.0523(6) Uani 1 1 d .
H8A H 0.9144 1.0121 0.5581 0.078 Uiso 0.50 1 calc PR
H8B H 0.8692 1.0058 0.6421 0.078 Uiso 0.50 1 calc PR
H8C H 0.6900 1.0761 0.5826 0.078 Uiso 0.50 1 calc PR
H8D H 0.7347 1.0505 0.6304 0.078 Uiso 0.50 1 calc PR
H8E H 0.7798 1.0569 0.5464 0.078 Uiso 0.50 1 calc PR
H8F H 0.9591 0.9866 0.6059 0.078 Uiso 0.50 1 calc PR
O1 O 0.2416(3) 0.60802(15) 0.51863(9) 0.0720(6) Uani 1 1 d .
H1 H 0.1088 0.6042 0.5444 0.086 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O9 H9 109.5
C12 C13 C14 117.44(17)
C12 C13 C16 121.53(16)
C14 C13 C16 121.03(17)
O9 C10 C11 121.46(16)
O9 C10 C15 118.47(16)
C11 C10 C15 120.07(17)
C2 C3 C4 119.42(18)
C2 C3 H3 120.3
C4 C3 H3 120.3
C15 C14 C13 121.67(17)
C15 C14 H14 119.2
C13 C14 H14 119.2
C11 C12 C13 121.77(16)
C11 C12 H12 119.1
C13 C12 H12 119.1
C4 C5 C6 117.38(16)
C4 C5 C8 120.88(18)
C6 C5 C8 121.73(18)
C3 C4 C5 122.01(17)
C3 C4 H4 119.0
C5 C4 H4 119.0
C10 C11 C12 119.38(17)
C10 C11 H11 120.3
C12 C11 H11 120.3
C14 C15 C10 119.67(17)
C14 C15 H15 120.2
C10 C15 H15 120.2
C3 C2 C7 120.37(17)
C3 C2 O1 116.69(19)
C7 C2 O1 122.94(19)
C5 C6 C7 121.38(17)
C5 C6 H6 119.3
C7 C6 H6 119.3
C2 C7 C6 119.44(17)
C2 C7 H7 120.3
C6 C7 H7 120.3
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C13 C16 H16D 109.5
H16A C16 H16D 141.1
H16B C16 H16D 56.3
H16C C16 H16D 56.3
C13 C16 H16E 109.5
H16A C16 H16E 56.3
H16B C16 H16E 141.1
H16C C16 H16E 56.3
H16D C16 H16E 109.5
C13 C16 H16F 109.5
H16A C16 H16F 56.3
H16B C16 H16F 56.3
H16C C16 H16F 141.1
H16D C16 H16F 109.5
H16E C16 H16F 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C5 C8 H8D 109.5
H8A C8 H8D 141.1
H8B C8 H8D 56.3
H8C C8 H8D 56.3
C5 C8 H8E 109.5
H8A C8 H8E 56.3
H8B C8 H8E 141.1
H8C C8 H8E 56.3
H8D C8 H8E 109.5
C5 C8 H8F 109.5
H8A C8 H8F 56.3
H8B C8 H8F 56.3
H8C C8 H8F 141.1
H8D C8 H8F 109.5
H8E C8 H8F 109.5
C2 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O9 C10 1.383(2)
O9 H9 0.9500
C13 C12 1.391(2)
C13 C14 1.393(3)
C13 C16 1.506(3)
C10 C11 1.385(2)
C10 C15 1.386(2)
C3 C2 1.373(3)
C3 C4 1.381(3)
C3 H3 0.9500
C14 C15 1.383(3)
C14 H14 0.9500
C12 C11 1.389(3)
C12 H12 0.9500
C5 C4 1.387(3)
C5 C6 1.387(3)
C5 C8 1.507(3)
C4 H4 0.9500
C11 H11 0.9500
C15 H15 0.9500
C2 C7 1.379(3)
C2 O1 1.383(2)
C6 C7 1.390(3)
C6 H6 0.9500
C7 H7 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C16 H16D 0.9800
C16 H16E 0.9800
C16 H16F 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C8 H8D 0.9800
C8 H8E 0.9800
C8 H8F 0.9800
O1 H1 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 O1 0.95 1.79 2.673(2) 153.8 3_566
O1 H1 O9 0.95 1.97 2.719(2) 134.1 .
