#------------------------------------------------------------------------------
#$Date: 2020-12-09 03:51:53 +0200 (Wed, 09 Dec 2020) $
#$Revision: 259670 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/75/7127517.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_7127517
loop_
_publ_author_name
'Yao, Liangliang'
'Fang, Bo'
'Hu, Qiong'
'Lei, Yu'
'Bao, Li'
'Hu, Yimin'
_publ_section_title
;
 Phenanthrenes/dihydrophenanthrenes: the selectivity controlled by
 different benzynes and allenes.
;
_journal_issue                   96
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              15185
_journal_page_last               15188
_journal_paper_doi               10.1039/d0cc06300b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-11-19 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1429(8)
_cell_length_b                   10.3536(9)
_cell_length_c                   16.2762(14)
_cell_measurement_reflns_used    6427
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.33
_cell_volume                     1485.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12590
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.331
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0529
_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
'w=1/[σ²(Fo²)+(0.0709P)²+0.2424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2724
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc06300b2.cif
_cod_data_source_block           190710a_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7127517
_shelx_shelxl_version_number     2018/1
_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   0.979
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_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
C1 C 1.0298(2) 1.03393(17) 0.35123(12) 0.0723(5) Uani 1 1 d . . . . .
H1A H 0.985777 1.090581 0.384817 0.109 Uiso 1 1 calc R U . . .
H1B H 1.054875 1.082310 0.306514 0.109 Uiso 1 1 calc R U . . .
H1C H 1.120090 0.995485 0.386786 0.109 Uiso 1 1 calc R U . . .
C2 C 0.9207(2) 0.93212(16) 0.31387(10) 0.0618(4) Uani 1 1 d . . . . .
H2A H 0.830558 0.969828 0.276119 0.074 Uiso 1 1 calc R U . . .
H2B H 0.965239 0.872930 0.281101 0.074 Uiso 1 1 calc R U . . .
C3 C 0.81568(14) 0.74837(13) 0.36538(8) 0.0411(3) Uani 1 1 d . . . . .
C4 C 0.78743(15) 0.68848(13) 0.44455(8) 0.0462(3) Uani 1 1 d . . . . .
H4A H 0.884062 0.663415 0.482563 0.055 Uiso 1 1 calc R U . . .
H4B H 0.742937 0.753240 0.473625 0.055 Uiso 1 1 calc R U . . .
C5 C 0.68470(14) 0.57203(12) 0.42759(7) 0.0396(3) Uani 1 1 d . . . . .
C6 C 0.74323(14) 0.45313(13) 0.44760(8) 0.0429(3) Uani 1 1 d . . . . .
H6 H 0.847112 0.445134 0.471616 0.051 Uiso 1 1 calc R U . . .
C7 C 0.65259(14) 0.33902(12) 0.43351(8) 0.0401(3) Uani 1 1 d . . . . .
C8 C 0.72226(17) 0.21777(14) 0.45309(9) 0.0510(3) Uani 1 1 d . . . . .
H8 H 0.826891 0.213511 0.475438 0.061 Uiso 1 1 calc R U . . .
C9 C 0.64015(19) 0.10643(14) 0.44009(10) 0.0566(4) Uani 1 1 d . . . . .
H9 H 0.687879 0.026875 0.453139 0.068 Uiso 1 1 calc R U . . .
C10 C 0.48383(18) 0.11368(13) 0.40701(9) 0.0534(4) Uani 1 1 d . . . . .
H10 H 0.426897 0.038067 0.397973 0.064 Uiso 1 1 calc R U . . .
C11 C 0.41192(16) 0.23039(13) 0.38742(8) 0.0455(3) Uani 1 1 d . . . . .
H11 H 0.307080 0.232032 0.365529 0.055 Uiso 1 1 calc R U . . .
C12 C 0.49314(14) 0.34841(11) 0.39965(7) 0.0359(3) Uani 1 1 d . . . . .
C13 C 0.42633(13) 0.47670(11) 0.37942(7) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.26747(14) 0.50176(12) 0.34768(7) 0.0395(3) Uani 1 1 d . . . . .
C15 C 0.21251(16) 0.62445(14) 0.32620(8) 0.0468(3) Uani 1 1 d . . . . .
H15 H 0.108822 0.637482 0.304275 0.056 Uiso 1 1 calc R U . . .
C16 C 0.31114(16) 0.72878(14) 0.33712(9) 0.0501(3) Uani 1 1 d . . . . .
H16 H 0.273285 0.811207 0.321718 0.060 Uiso 1 1 calc R U . . .
C17 C 0.46285(16) 0.71121(13) 0.37023(8) 0.0451(3) Uani 1 1 d . . . . .
H17 H 0.527339 0.782268 0.378612 0.054 Uiso 1 1 calc R U . . .
C18 C 0.52370(14) 0.58707(12) 0.39199(7) 0.0369(3) Uani 1 1 d . . . . .
C19 C 0.01363(16) 0.41898(17) 0.30984(11) 0.0610(4) Uani 1 1 d . . . . .
H19A H -0.019171 0.476209 0.347830 0.092 Uiso 1 1 calc R U . . .
H19B H -0.038765 0.338064 0.306939 0.092 Uiso 1 1 calc R U . . .
H19C H -0.008440 0.456903 0.254074 0.092 Uiso 1 1 calc R U . . .
O1 O 0.88119(13) 0.86335(10) 0.38328(6) 0.0569(3) Uani 1 1 d . . . . .
O2 O 0.78759(14) 0.69994(11) 0.29645(7) 0.0672(3) Uani 1 1 d . . . . .
O3 O 0.17191(10) 0.39799(10) 0.34036(6) 0.0520(3) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 108.07(13) . . ?
O1 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
O1 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O2 C3 O1 123.68(12) . . ?
O2 C3 C4 125.87(12) . . ?
O1 C3 C4 110.43(11) . . ?
C5 C4 C3 114.23(10) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C18 119.61(11) . . ?
C6 C5 C4 119.87(11) . . ?
C18 C5 C4 120.51(11) . . ?
C5 C6 C7 122.77(11) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C8 C7 C12 120.44(12) . . ?
C8 C7 C6 119.62(12) . . ?
C12 C7 C6 119.94(11) . . ?
C9 C8 C7 121.53(13) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 118.87(13) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 121.19(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.74(13) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C7 116.23(11) . . ?
C11 C12 C13 125.44(11) . . ?
C7 C12 C13 118.33(11) . . ?
C18 C13 C14 116.16(11) . . ?
C18 C13 C12 119.12(10) . . ?
C14 C13 C12 124.72(11) . . ?
O3 C14 C15 121.34(11) . . ?
O3 C14 C13 116.89(11) . . ?
C15 C14 C13 121.77(12) . . ?
C14 C15 C16 120.30(12) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.41(12) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.00(12) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 120.28(11) . . ?
C17 C18 C5 119.56(11) . . ?
C13 C18 C5 120.16(11) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 O1 C2 117.18(11) . . ?
C14 O3 C19 118.61(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.468(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.4595(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.1930(16) . ?
C3 O1 1.3297(16) . ?
C3 C4 1.5128(17) . ?
C4 C5 1.5082(17) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.3474(18) . ?
C5 C18 1.4404(17) . ?
C6 C7 1.4264(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.4056(18) . ?
C7 C12 1.4186(17) . ?
C8 C9 1.361(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.3722(19) . ?
C10 H10 0.9300 . ?
C11 C12 1.4163(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.4626(16) . ?
C13 C18 1.4295(17) . ?
C13 C14 1.4304(17) . ?
C14 O3 1.3699(16) . ?
C14 C15 1.3766(18) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3606(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.4080(17) . ?
C17 H17 0.9300 . ?
C19 O3 1.4167(17) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
