#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/71/2207140.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_2207140
loop_
_publ_author_name
'Li, Jie'
'Ma, Jian-Ping'
'Huang, Ru-Qi'
'Dong, Yu-Bin'
_publ_section_title
;
 6-[4-(2-Chloroethyloxy)naphthyl]fulvene
;
_journal_coeditor_code           BH6042
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3901
_journal_page_last               o3902
_journal_paper_doi               10.1107/S1600536805034483
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H15 Cl O'
_chemical_formula_moiety         'C18 H15 Cl O'
_chemical_formula_sum            'C18 H15 Cl O'
_chemical_formula_weight         282.75
_chemical_name_systematic
;
6-[4-(2-Chloroethyloxy)naphthyl]fulvene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.764(9)
_cell_length_b                   7.361(5)
_cell_length_c                   31.03(2)
_cell_measurement_reflns_used    1401
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.096
_cell_measurement_theta_min      3.073
_cell_volume                     2915(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16129
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0619
_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)+(0.0557P)²+0.0844P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                1764
_reflns_number_total             3175
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh6042.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2915(4)
_cod_database_code               2207140
_cod_database_fobs_code          2207140
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.81614(19) -0.0343(3) 0.22830(9) 0.0586(7) Uani d . 1 C
H1 0.7716 -0.0974 0.2467 0.070 Uiso calc R 1 H
C2 0.8176(2) -0.0469(4) 0.18574(9) 0.0695(8) Uani d . 1 C
H2 0.7735 -0.1201 0.1693 0.083 Uiso calc R 1 H
C3 0.8982(2) 0.0708(4) 0.16876(9) 0.0753(8) Uani d . 1 C
H3 0.9146 0.0853 0.1398 0.090 Uiso calc R 1 H
C4 0.9452(2) 0.1549(4) 0.20147(8) 0.0672(8) Uani d . 1 C
H4 1.0000 0.2376 0.1992 0.081 Uiso calc R 1 H
C5 0.89633(18) 0.0957(3) 0.24134(7) 0.0526(6) Uani d . 1 C
C6 0.92446(19) 0.1513(3) 0.28097(7) 0.0563(6) Uani d . 1 C
H6 0.9808 0.2312 0.2824 0.068 Uiso calc R 1 H
C7 0.87689(18) 0.1008(3) 0.32196(7) 0.0491(6) Uani d . 1 C
C8 0.77066(19) 0.0880(3) 0.32688(8) 0.0558(6) Uani d . 1 C
H8 0.7283 0.1085 0.3030 0.067 Uiso calc R 1 H
C9 0.72276(19) 0.0456(3) 0.36620(8) 0.0568(7) Uani d . 1 C
H9 0.6501 0.0420 0.3684 0.068 Uiso calc R 1 H
C10 0.78357(19) 0.0097(3) 0.40125(8) 0.0516(6) Uani d . 1 C
C11 0.63744(18) -0.0497(4) 0.44760(8) 0.0594(7) Uani d . 1 C
H11A 0.6071 -0.1297 0.4261 0.071 Uiso calc R 1 H
H11B 0.6042 0.0684 0.4453 0.071 Uiso calc R 1 H
C12 0.62255(19) -0.1262(4) 0.49161(8) 0.0675(8) Uani d . 1 C
H12A 0.6668 -0.2324 0.4949 0.081 Uiso calc R 1 H
H12B 0.5503 -0.1650 0.4948 0.081 Uiso calc R 1 H
C13 0.89503(18) 0.0183(3) 0.39879(7) 0.0475(6) Uani d . 1 C
C14 0.95943(19) -0.0170(3) 0.43487(7) 0.0547(7) Uani d . 1 C
H14 0.9291 -0.0536 0.4607 0.066 Uiso calc R 1 H
C15 1.0651(2) 0.0019(3) 0.43231(8) 0.0614(7) Uani d . 1 C
H15 1.1064 -0.0186 0.4565 0.074 Uiso calc R 1 H
C16 1.1115(2) 0.0519(4) 0.39347(8) 0.0650(7) Uani d . 1 C
H16 1.1838 0.0657 0.3920 0.078 Uiso calc R 1 H
C17 1.05228(19) 0.0808(3) 0.35782(7) 0.0571(7) Uani d . 1 C
H17 1.0851 0.1099 0.3320 0.069 Uiso calc R 1 H
C18 0.94150(18) 0.0676(3) 0.35908(7) 0.0464(6) Uani d . 1 C
O1 0.74788(13) -0.0341(2) 0.44129(5) 0.0638(5) Uani d . 1 O
Cl1 0.65275(6) 0.03160(13) 0.53284(2) 0.0901(3) Uani d . 1 Cl
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C2 C1 C5 108.3(2) ?
C2 C1 H1 125.9 ?
C5 C1 H1 125.9 ?
C1 C2 C3 109.3(2) ?
C1 C2 H2 125.3 ?
C3 C2 H2 125.3 ?
C4 C3 C2 108.8(3) ?
C4 C3 H3 125.6 ?
C2 C3 H3 125.6 ?
C3 C4 C5 108.4(3) ?
C3 C4 H4 125.8 ?
C5 C4 H4 125.8 ?
C6 C5 C4 125.0(2) ?
C6 C5 C1 129.9(2) ?
C4 C5 C1 105.2(2) ?
C5 C6 C7 127.5(2) yes
C5 C6 H6 116.2 ?
C7 C6 H6 116.2 ?
C8 C7 C18 117.9(2) ?
C8 C7 C6 121.9(2) ?
C18 C7 C6 120.2(2) ?
C7 C8 C9 123.1(2) ?
C7 C8 H8 118.5 ?
C9 C8 H8 118.5 ?
C10 C9 C8 119.4(2) ?
C10 C9 H9 120.3 ?
C8 C9 H9 120.3 ?
O1 C10 C9 125.7(2) ?
O1 C10 C13 113.2(2) ?
C9 C10 C13 121.1(2) ?
O1 C11 C12 106.4(2) ?
O1 C11 H11A 110.5 ?
C12 C11 H11A 110.5 ?
O1 C11 H11B 110.5 ?
C12 C11 H11B 110.5 ?
H11A C11 H11B 108.6 ?
C11 C12 Cl1 112.8(2) ?
C11 C12 H12A 109.0 ?
Cl1 C12 H12A 109.0 ?
C11 C12 H12B 109.0 ?
Cl1 C12 H12B 109.0 ?
H12A C12 H12B 107.8 ?
C14 C13 C18 119.6(2) ?
C14 C13 C10 122.0(2) ?
C18 C13 C10 118.4(2) ?
C15 C14 C13 120.8(2) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 120.0(2) ?
C14 C15 H15 120.0 ?
C16 C15 H15 120.0 ?
C17 C16 C15 120.7(2) ?
C17 C16 H16 119.6 ?
C15 C16 H16 119.6 ?
C16 C17 C18 121.5(2) ?
C16 C17 H17 119.3 ?
C18 C17 H17 119.3 ?
C13 C18 C17 117.4(2) ?
C13 C18 C7 120.1(2) ?
C17 C18 C7 122.6(2) ?
C10 O1 C11 118.32(19) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.324(3) yes
C1 C5 1.458(3) ?
C1 H1 0.9300 ?
C2 C3 1.445(4) ?
C2 H2 0.9300 ?
C3 C4 1.332(4) yes
C3 H3 0.9300 ?
C4 C5 1.452(3) ?
C4 H4 0.9300 ?
C5 C6 1.345(3) yes
C6 C7 1.457(3) yes
C6 H6 0.9300 ?
C7 C8 1.368(3) ?
C7 C18 1.438(3) ?
C8 C9 1.400(3) ?
C8 H8 0.9300 ?
C9 C10 1.362(3) ?
C9 H9 0.9300 ?
C10 O1 1.362(3) yes
C10 C13 1.426(3) ?
C11 O1 1.428(3) yes
C11 C12 1.489(3) yes
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 Cl1 1.770(3) yes
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 C14 1.413(3) ?
C13 C18 1.415(3) ?
C14 C15 1.358(3) ?
C14 H14 0.9300 ?
C15 C16 1.392(3) ?
C15 H15 0.9300 ?
C16 C17 1.356(3) ?
C16 H16 0.9300 ?
C17 C18 1.418(3) ?
C17 H17 0.9300 ?
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
C5 C1 C2 C3 0.6(3)
C1 C2 C3 C4 -0.2(3)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 179.3(2)
C3 C4 C5 C1 0.6(3)
C2 C1 C5 C6 -179.3(3)
C2 C1 C5 C4 -0.7(3)
C4 C5 C6 C7 178.2(2)
C1 C5 C6 C7 -3.4(4)
C5 C6 C7 C8 -41.4(4)
C5 C6 C7 C18 140.3(3)
C18 C7 C8 C9 0.4(4)
C6 C7 C8 C9 -177.9(2)
C7 C8 C9 C10 -2.0(4)
C8 C9 C10 O1 -179.7(2)
C8 C9 C10 C13 1.3(4)
O1 C11 C12 Cl1 71.7(2)
O1 C10 C13 C14 0.3(3)
C9 C10 C13 C14 179.5(2)
O1 C10 C13 C18 -178.28(19)
C9 C10 C13 C18 0.8(3)
C18 C13 C14 C15 2.3(3)
C10 C13 C14 C15 -176.3(2)
C13 C14 C15 C16 -1.7(4)
C14 C15 C16 C17 -0.6(4)
C15 C16 C17 C18 2.3(4)
C14 C13 C18 C17 -0.6(3)
C10 C13 C18 C17 178.1(2)
C14 C13 C18 C7 178.9(2)
C10 C13 C18 C7 -2.4(3)
C16 C17 C18 C13 -1.6(4)
C16 C17 C18 C7 178.8(2)
C8 C7 C18 C13 1.8(3)
C6 C7 C18 C13 -179.9(2)
C8 C7 C18 C17 -178.7(2)
C6 C7 C18 C17 -0.4(4)
C9 C10 O1 C11 1.9(3)
C13 C10 O1 C11 -179.0(2)
C12 C11 O1 C10 171.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128688
