#------------------------------------------------------------------------------
#$Date: 2022-03-09 11:11:12 +0200 (Wed, 09 Mar 2022) $
#$Revision: 273555 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104694.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_8104694
loop_
_publ_author_name
'Zhang, Xing-Yu'
'Chen, Wei-chi'
'Liu, Mei-Feng'
_publ_section_title
;
 Crystal structure of 7-hydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene
 from Arundina graminifolia, C16H16O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              729
_journal_page_last               730
_journal_paper_doi               10.1515/ncrs-2021-0053
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.59
_chemical_name_systematic
;
7-hydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 103.093(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.548(3)
_cell_length_b                   13.426(4)
_cell_length_c                   11.369(3)
_cell_measurement_reflns_used    5307
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.38
_cell_volume                     1270.8(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013) '
_computing_data_collection       'SAINT v8.34A (Bruker, 2013) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013) '
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) '
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) '
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) '
_computing_structure_solution    'ShelXT (Sheldrick, 2015) '
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans '
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14046
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
ADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0645 before and 0.0310 after correction.
The Ratio of minimum to maximum transmission is 0.9543.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            ' colourless'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
;
_refine_ls_abs_structure_Flack
;
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0421
_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)+(0.0720P)²+0.1773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1243
_cod_data_source_file            suppl_j_ncrs-2021-0053_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1270.7(7)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               8104694
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42123(12) 0.32864(7) 0.31967(8) 0.0493(3) Uani 1 1 d . . . . .
O2 O 0.25349(13) 0.45973(8) 1.13515(9) 0.0530(3) Uani 1 1 d . . . . .
H2 H 0.316(2) 0.4187(16) 1.1893(19) 0.080 Uiso 1 1 d R . . . .
O3 O 0.21729(12) 0.54610(7) 0.57691(8) 0.0468(3) Uani 1 1 d . . . . .
C1 C 0.5110(2) 0.24231(13) 0.30350(14) 0.0623(4) Uani 1 1 d . . . . .
H1A H 0.615528 0.245537 0.356780 0.093 Uiso 1 1 calc GR . . . .
H1B H 0.522023 0.239355 0.221385 0.093 Uiso 1 1 calc GR . . . .
H1C H 0.456020 0.183874 0.321435 0.093 Uiso 1 1 calc GR . . . .
C2 C 0.40129(15) 0.34725(9) 0.43434(11) 0.0370(3) Uani 1 1 d . . . . .
C3 C 0.31873(15) 0.43410(9) 0.44756(11) 0.0386(3) Uani 1 1 d . . . . .
H3 H 0.280179 0.474844 0.381156 0.046 Uiso 1 1 calc R . . . .
C4 C 0.29403(14) 0.45983(9) 0.55961(11) 0.0351(3) Uani 1 1 d . . . . .
C5 C 0.34971(14) 0.39944(9) 0.66266(10) 0.0331(3) Uani 1 1 d . . . . .
C6 C 0.32572(14) 0.42118(9) 0.78570(10) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.20378(15) 0.48176(9) 0.81006(11) 0.0380(3) Uani 1 1 d . . . . .
H7 H 0.135367 0.514309 0.746404 0.046 Uiso 1 1 calc R . . . .
C8 C 0.18177(16) 0.49477(10) 0.92623(12) 0.0415(3) Uani 1 1 d . . . . .
H8 H 0.099605 0.535601 0.939556 0.050 Uiso 1 1 calc R . . . .
C9 C 0.28154(16) 0.44726(9) 1.02187(11) 0.0396(3) Uani 1 1 d . . . . .
C10 C 0.14919(18) 0.60471(10) 0.47414(12) 0.0478(3) Uani 1 1 d . . . . .
H10A H 0.232008 0.624701 0.434444 0.072 Uiso 1 1 calc GR . . . .
H10B H 0.099639 0.662774 0.499058 0.072 Uiso 1 1 calc GR . . . .
H10C H 0.069862 0.566303 0.419420 0.072 Uiso 1 1 calc GR . . . .
C11 C 0.43248(14) 0.31249(9) 0.64490(11) 0.0361(3) Uani 1 1 d . . . . .
C12 C 0.49697(17) 0.24566(10) 0.75184(12) 0.0430(3) Uani 1 1 d . . . . .
H12A H 0.582515 0.204302 0.735274 0.052 Uiso 1 1 calc R . . . .
H12B H 0.412160 0.202325 0.765734 0.052 Uiso 1 1 calc R . . . .
C13 C 0.56047(16) 0.30843(10) 0.86311(12) 0.0419(3) Uani 1 1 d . . . . .
H13A H 0.598401 0.265638 0.932461 0.050 Uiso 1 1 calc R . . . .
H13B H 0.649854 0.348750 0.851360 0.050 Uiso 1 1 calc R . . . .
C14 C 0.42788(14) 0.37460(9) 0.88517(11) 0.0350(3) Uani 1 1 d . . . . .
C15 C 0.40543(15) 0.38829(9) 1.00088(11) 0.0383(3) Uani 1 1 d . . . . .
H15 H 0.474591 0.357427 1.065560 0.046 Uiso 1 1 calc R . . . .
C16 C 0.45825(15) 0.28634(9) 0.53216(11) 0.0377(3) Uani 1 1 d . . . . .
H16 H 0.513471 0.228202 0.523047 0.045 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 0.000 0.000
;
International Tables Vol C Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
;
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 C1 117.13(10) . .
C9 O2 H2 111.1(13) . .
C4 O3 C10 118.16(10) . .
O1 C1 H1A 109.5 . .
O1 C1 H1B 109.5 . .
O1 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C3 115.48(11) . .
O1 C2 C16 124.08(11) . .
C16 C2 C3 120.44(11) . .
C2 C3 H3 120.1 . .
C4 C3 C2 119.82(11) . .
C4 C3 H3 120.1 . .
O3 C4 C3 121.54(11) . .
O3 C4 C5 116.64(11) . .
C3 C4 C5 121.81(11) . .
C4 C5 C6 125.00(11) . .
C11 C5 C4 116.32(11) . .
C11 C5 C6 118.68(10) . .
C7 C6 C5 124.61(11) . .
C7 C6 C14 116.97(11) . .
C14 C6 C5 118.37(11) . .
C6 C7 H7 119.0 . .
C8 C7 C6 122.00(11) . .
C8 C7 H7 119.0 . .
C7 C8 H8 120.0 . .
C9 C8 C7 120.02(12) . .
C9 C8 H8 120.0 . .
O2 C9 C8 118.41(12) . .
O2 C9 C15 122.28(11) . .
C8 C9 C15 119.31(12) . .
O3 C10 H10A 109.5 . .
O3 C10 H10B 109.5 . .
O3 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C5 C11 C12 118.82(11) . .
C16 C11 C5 122.13(11) . .
C16 C11 C12 119.04(11) . .
C11 C12 H12A 109.7 . .
C11 C12 H12B 109.7 . .
C11 C12 C13 109.76(11) . .
H12A C12 H12B 108.2 . .
C13 C12 H12A 109.7 . .
C13 C12 H12B 109.7 . .
C12 C13 H13A 109.9 . .
C12 C13 H13B 109.9 . .
H13A C13 H13B 108.3 . .
C14 C13 C12 109.06(10) . .
C14 C13 H13A 109.9 . .
C14 C13 H13B 109.9 . .
C6 C14 C13 118.78(11) . .
C15 C14 C6 120.65(11) . .
C15 C14 C13 120.56(11) . .
C9 C15 H15 119.5 . .
C14 C15 C9 121.03(11) . .
C14 C15 H15 119.5 . .
C2 C16 C11 119.49(11) . .
C2 C16 H16 120.3 . .
C11 C16 H16 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.4249(17) .
O1 C2 1.3754(15) .
O2 H2 0.91(2) .
O2 C9 1.3726(15) .
O3 C4 1.3672(15) .
O3 C10 1.4195(15) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.3887(17) .
C2 C16 1.3774(18) .
C3 H3 0.9300 .
C3 C4 1.3815(17) .
C4 C5 1.4156(17) .
C5 C6 1.4878(16) .
C5 C11 1.4032(17) .
C6 C7 1.3983(17) .
C6 C14 1.4089(17) .
C7 H7 0.9300 .
C7 C8 1.3867(17) .
C8 H8 0.9300 .
C8 C9 1.3771(19) .
C9 C15 1.3855(19) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.5110(17) .
C11 C16 1.3937(17) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.5146(19) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.5052(17) .
C14 C15 1.3840(17) .
C15 H15 0.9300 .
C16 H16 0.9300 .
