#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/75/4027552.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_4027552
loop_
_publ_author_name
'Krishnendu Bera'
'Soumen Sarkar'
'Swapnadeep Jalal'
'Umasish Jana'
_publ_section_title
;
 Synthesis of Substituted Phenanthrene by Iron(III)-Catalyzed
 Intramolecular Alkyne-Carbonyl Metathesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8780
_journal_page_last               8786
_journal_paper_doi               10.1021/jo301371n
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C22 H16 O'
_chemical_formula_weight         296.35
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.067(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9052(2)
_cell_length_b                   10.4099(3)
_cell_length_c                   15.6229(4)
_cell_measurement_reflns_used    4178
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.27
_cell_volume                     1586.11(7)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12878
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9139
_exptl_absorpt_correction_T_min  0.8721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       rectanguler
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0046(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0499
_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)+(0.0754P)²+0.2796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                2640
_reflns_number_total             3635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301371n_si_001.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4027552
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
O1 O 1.14541(11) 0.87162(12) 0.13860(9) 0.0661(4) Uani 1 1 d .
C1 C 0.9614(2) 1.19533(19) 0.32099(12) 0.0690(5) Uani 1 1 d .
H1 H 0.9482 1.2577 0.3613 0.083 Uiso 1 1 calc R
C2 C 0.85857(18) 1.10969(17) 0.29139(10) 0.0557(4) Uani 1 1 d .
H2 H 0.7759 1.1139 0.3117 0.067 Uiso 1 1 calc R
C3 C 0.87804(14) 1.01752(15) 0.23152(9) 0.0442(4) Uani 1 1 d .
H3 H 0.8076 0.9605 0.2109 0.053 Uiso 1 1 calc R
C4 C 1.00150(13) 1.00878(14) 0.20153(9) 0.0404(3) Uani 1 1 d .
C5 C 1.02847(14) 0.90491(14) 0.14150(10) 0.0440(3) Uani 1 1 d .
C6 C 0.90896(14) 0.84389(14) 0.08352(9) 0.0420(3) Uani 1 1 d .
C7 C 0.89604(15) 0.70592(14) 0.07491(9) 0.0423(3) Uani 1 1 d .
C8 C 0.78427(16) 0.65389(15) 0.01611(9) 0.0446(4) Uani 1 1 d .
C9 C 0.76921(19) 0.51902(16) 0.01260(11) 0.0549(4) Uani 1 1 d .
H9 H 0.6962 0.4840 -0.0259 0.066 Uiso 1 1 calc R
C10 C 0.8578(2) 0.43761(16) 0.06361(11) 0.0582(5) Uani 1 1 d .
C11 C 0.8377(3) 0.29438(16) 0.05977(14) 0.0782(6) Uani 1 1 d .
H11A H 0.7635 0.2735 0.0136 0.117 Uiso 1 1 calc R
H11B H 0.8165 0.2645 0.1140 0.117 Uiso 1 1 calc R
H11C H 0.9202 0.2537 0.0492 0.117 Uiso 1 1 calc R
C12 C 0.98692(17) 0.62169(15) 0.12629(10) 0.0512(4) Uani 1 1 d .
H12 H 1.0613 0.6547 0.1646 0.061 Uiso 1 1 calc R
C13 C 0.96724(19) 0.49017(17) 0.12061(11) 0.0588(5) Uani 1 1 d .
H13 H 1.0283 0.4361 0.1555 0.071 Uiso 1 1 calc R
C14 C 0.68751(16) 0.73906(15) -0.03740(9) 0.0457(4) Uani 1 1 d .
C15 C 0.57814(19) 0.69520(18) -0.09947(11) 0.0635(5) Uani 1 1 d .
H15 H 0.5653 0.6074 -0.1082 0.076 Uiso 1 1 calc R
C16 C 0.4896(2) 0.7795(2) -0.14757(13) 0.0722(6) Uani 1 1 d .
H16 H 0.4177 0.7479 -0.1885 0.087 Uiso 1 1 calc R
C17 C 0.50508(18) 0.9108(2) -0.13640(11) 0.0645(5) Uani 1 1 d .
H17 H 0.4438 0.9670 -0.1692 0.077 Uiso 1 1 calc R
C18 C 0.61186(17) 0.95724(17) -0.07641(10) 0.0552(4) Uani 1 1 d .
H18 H 0.6230 1.0455 -0.0688 0.066 Uiso 1 1 calc R
C19 C 0.70399(15) 0.87337(15) -0.02661(9) 0.0450(4) Uani 1 1 d .
C20 C 0.81489(15) 0.92252(14) 0.03510(10) 0.0451(4) Uani 1 1 d .
H20 H 0.8235 1.0109 0.0427 0.054 Uiso 1 1 calc R
C21 C 1.10521(16) 1.09567(17) 0.23237(11) 0.0570(4) Uani 1 1 d .
H21 H 1.1889 1.0907 0.2134 0.068 Uiso 1 1 calc R
C22 C 1.0840(2) 1.18919(19) 0.29115(13) 0.0723(6) Uani 1 1 d .
H22 H 1.1529 1.2484 0.3107 0.087 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
C2 C1 C22 120.19(17)
C2 C1 H1 119.9
C22 C1 H1 119.9
C1 C2 C3 119.87(16)
C1 C2 H2 120.1
C3 C2 H2 120.1
C2 C3 C4 120.77(14)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C21 118.82(14)
C3 C4 C5 121.83(13)
C21 C4 C5 119.26(13)
O1 C5 C4 120.52(13)
O1 C5 C6 120.83(14)
C4 C5 C6 118.64(12)
C20 C6 C7 120.21(13)
C20 C6 C5 118.08(13)
C7 C6 C5 121.62(13)
C12 C7 C8 118.84(14)
C12 C7 C6 121.98(14)
C8 C7 C6 119.10(13)
C9 C8 C7 118.07(15)
C9 C8 C14 121.89(14)
C7 C8 C14 120.03(13)
C10 C9 C8 122.67(16)
C10 C9 H9 118.7
C8 C9 H9 118.7
C9 C10 C13 118.53(15)
C9 C10 C11 121.54(19)
C13 C10 C11 119.93(18)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C7 120.81(16)
C13 C12 H12 119.6
C7 C12 H12 119.6
C12 C13 C10 121.08(16)
C12 C13 H13 119.5
C10 C13 H13 119.5
C15 C14 C19 117.70(15)
C15 C14 C8 123.46(15)
C19 C14 C8 118.85(13)
C16 C15 C14 121.04(17)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C17 121.21(16)
C15 C16 H16 119.4
C17 C16 H16 119.4
C18 C17 C16 119.31(17)
C18 C17 H17 120.3
C16 C17 H17 120.3
C17 C18 C19 120.69(17)
C17 C18 H18 119.7
C19 C18 H18 119.7
C18 C19 C14 120.06(14)
C18 C19 C20 120.26(14)
C14 C19 C20 119.69(14)
C6 C20 C19 122.05(14)
C6 C20 H20 119.0
C19 C20 H20 119.0
C22 C21 C4 120.05(16)
C22 C21 H21 120.0
C4 C21 H21 120.0
C1 C22 C21 120.28(17)
C1 C22 H22 119.9
C21 C22 H22 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.2175(17)
C1 C2 1.372(2)
C1 C22 1.376(3)
C1 H1 0.9300
C2 C3 1.377(2)
C2 H2 0.9300
C3 C4 1.3870(19)
C3 H3 0.9300
C4 C21 1.390(2)
C4 C5 1.486(2)
C5 C6 1.5001(19)
C6 C20 1.365(2)
C6 C7 1.446(2)
C7 C12 1.404(2)
C7 C8 1.417(2)
C8 C9 1.412(2)
C8 C14 1.457(2)
C9 C10 1.370(2)
C9 H9 0.9300
C10 C13 1.390(3)
C10 C11 1.504(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.384(2)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.398(2)
C14 C19 1.414(2)
C15 C16 1.369(3)
C15 H15 0.9300
C16 C17 1.383(3)
C16 H16 0.9300
C17 C18 1.373(2)
C17 H17 0.9300
C18 C19 1.397(2)
C18 H18 0.9300
C19 C20 1.424(2)
C20 H20 0.9300
C21 C22 1.379(2)
C21 H21 0.9300
C22 H22 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659540
