#------------------------------------------------------------------------------
#$Date: 2020-12-23 08:30:48 +0200 (Wed, 23 Dec 2020) $
#$Revision: 260119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559849.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1559849
loop_
_publ_author_name
'Nazarenko, Alexander Y.'
_publ_section_title
;
 Naphthalen-1-ylmethanol
;
_journal_coeditor_code           HB4373
_journal_issue                   12
_journal_name_full               IUCrData
_journal_page_first              x201646
_journal_paper_doi               10.1107/S2414314620016466
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C11 H10 O'
_chemical_formula_moiety         'C11 H10 O'
_chemical_formula_sum            'C11 H10 O'
_chemical_formula_weight         158.19
_chemical_melting_point          333
_chemical_name_common            1-naphthalenemethanol
_chemical_name_systematic
;
Naphthalen-1-ylmethanol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.93060(10)
_cell_length_b                   15.7882(5)
_cell_length_c                   21.0651(6)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.98
_cell_measurement_theta_min      3.23
_cell_volume                     1639.82(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2020)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker PHOTON-100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            38547
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.085
_diffrn_reflns_theta_min         3.225
_diffrn_source                   sealedtube
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0706P)²+0.4678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                2146
_reflns_number_total             2860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4373sup1.cif
_cod_data_source_block           I
_cod_database_code               1559849
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.64002(18) 0.45528(6) 0.27894(4) 0.0398(2) Uani d 1 . .
H H1 0.788(5) 0.4551(11) 0.2541(10) 0.068(5) Uiso d 1 . .
C C1 0.5128(2) 0.39728(7) 0.38094(5) 0.0288(2) Uani d 1 . .
C C2 0.3861(2) 0.43905(7) 0.42978(5) 0.0330(2) Uani d 1 . .
H H2 0.441(3) 0.4976(9) 0.4386(7) 0.041(4) Uiso d 1 . .
C C3 0.1852(3) 0.39961(8) 0.46739(6) 0.0352(3) Uani d 1 . .
H H3 0.102(3) 0.4281(10) 0.5013(8) 0.045(4) Uiso d 1 . .
C C4 0.1114(2) 0.31785(7) 0.45523(5) 0.0325(2) Uani d 1 . .
H H4 -0.027(3) 0.2898(9) 0.4812(7) 0.042(4) Uiso d 1 . .
C C5 0.2393(2) 0.27146(7) 0.40600(5) 0.0276(2) Uani d 1 . .
C C6 0.1723(3) 0.18527(7) 0.39480(6) 0.0344(3) Uani d 1 . .
H H6 0.027(3) 0.1588(9) 0.4205(7) 0.044(4) Uiso d 1 . .
C C7 0.3045(3) 0.13985(8) 0.34904(6) 0.0388(3) Uani d 1 . .
H H7 0.259(4) 0.0829(11) 0.3412(8) 0.050(4) Uiso d 1 . .
C C8 0.5083(3) 0.17819(8) 0.31230(6) 0.0390(3) Uani d 1 . .
H H8 0.607(3) 0.1454(10) 0.2784(8) 0.050(4) Uiso d 1 . .
C C9 0.5750(2) 0.26132(8) 0.32101(5) 0.0336(3) Uani d 1 . .
H H9 0.714(3) 0.2873(10) 0.2953(7) 0.046(4) Uiso d 1 . .
C C10 0.4438(2) 0.31084(7) 0.36840(5) 0.0268(2) Uani d 1 . .
C C11 0.7284(2) 0.44171(8) 0.34298(6) 0.0349(3) Uani d 1 . .
H H11A 0.777(3) 0.4958(10) 0.3634(7) 0.041(4) Uiso d 1 . .
H H11B 0.902(3) 0.4052(9) 0.3427(7) 0.039(4) Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 H1 . . 107.5(14) ?
C2 C1 C10 . . 119.25(10) ?
C2 C1 C11 . . 119.75(10) ?
C10 C1 C11 . . 120.97(10) ?
C1 C2 H2 . . 118.0(9) ?
C1 C2 C3 . . 121.85(11) ?
C3 C2 H2 . . 120.1(9) ?
C2 C3 H3 . . 121.5(10) ?
C4 C3 C2 . . 119.88(11) ?
C4 C3 H3 . . 118.6(10) ?
C3 C4 H4 . . 120.5(9) ?
C3 C4 C5 . . 120.48(11) ?
C5 C4 H4 . . 119.0(9) ?
C4 C5 C6 . . 120.88(10) ?
C4 C5 C10 . . 119.74(10) ?
C6 C5 C10 . . 119.36(10) ?
C5 C6 H6 . . 118.8(9) ?
C7 C6 C5 . . 120.60(11) ?
C7 C6 H6 . . 120.6(9) ?
C6 C7 H7 . . 120.8(11) ?
C6 C7 C8 . . 120.22(11) ?
C8 C7 H7 . . 119.0(11) ?
C7 C8 H8 . . 121.0(9) ?
C9 C8 C7 . . 120.80(11) ?
C9 C8 H8 . . 118.2(9) ?
C8 C9 H9 . . 120.3(9) ?
C8 C9 C10 . . 120.87(11) ?
C10 C9 H9 . . 118.8(10) ?
C5 C10 C1 . . 118.78(10) ?
C9 C10 C1 . . 123.06(10) ?
C9 C10 C5 . . 118.14(10) ?
O1 C11 C1 . . 110.79(9) ?
O1 C11 H11A . . 110.7(9) ?
O1 C11 H11B . . 109.3(8) ?
C1 C11 H11A . . 110.1(9) ?
C1 C11 H11B . . 109.2(9) ?
H11A C11 H11B . . 106.5(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 H1 . 0.90(2) ?
O1 C11 . 1.4338(14) ?
C1 C2 . 1.3724(16) ?
C1 C10 . 1.4310(15) ?
C1 C11 . 1.5039(16) ?
C2 H2 . 0.980(15) ?
C2 C3 . 1.4131(17) ?
C3 H3 . 0.939(16) ?
C3 C4 . 1.3654(17) ?
C4 H4 . 0.981(15) ?
C4 C5 . 1.4174(15) ?
C5 C6 . 1.4201(16) ?
C5 C10 . 1.4252(14) ?
C6 H6 . 0.989(17) ?
C6 C7 . 1.3669(18) ?
C7 H7 . 0.940(17) ?
C7 C8 . 1.4054(19) ?
C8 H8 . 1.006(17) ?
C8 C9 . 1.3653(18) ?
C9 H9 . 0.965(16) ?
C9 C10 . 1.4232(16) ?
C11 H11A . 0.986(16) ?
C11 H11B . 1.032(16) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O1 6_656 0.90(2) 1.87(2) 2.7504(8) 166(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . -0.39(18) ?
C2 C1 C10 C5 . . . . 1.81(15) ?
C2 C1 C10 C9 . . . . -176.55(10) ?
C2 C1 C11 O1 . . . . -113.15(12) ?
C2 C3 C4 C5 . . . . 1.44(17) ?
C3 C4 C5 C6 . . . . 177.24(11) ?
C3 C4 C5 C10 . . . . -0.83(16) ?
C4 C5 C6 C7 . . . . -177.20(11) ?
C4 C5 C10 C1 . . . . -0.80(15) ?
C4 C5 C10 C9 . . . . 177.65(10) ?
C5 C6 C7 C8 . . . . -0.22(19) ?
C6 C5 C10 C1 . . . . -178.90(10) ?
C6 C5 C10 C9 . . . . -0.45(15) ?
C6 C7 C8 C9 . . . . -0.9(2) ?
C7 C8 C9 C10 . . . . 1.34(19) ?
C8 C9 C10 C1 . . . . 177.73(11) ?
C8 C9 C10 C5 . . . . -0.64(17) ?
C10 C1 C2 C3 . . . . -1.25(17) ?
C10 C1 C11 O1 . . . . 69.09(14) ?
C10 C5 C6 C7 . . . . 0.88(17) ?
C11 C1 C2 C3 . . . . -179.05(10) ?
C11 C1 C10 C5 . . . . 179.58(9) ?
C11 C1 C10 C9 . . . . 1.22(16) ?

_cod_database_fobs_code 1559849
