#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:52:38 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/13/2001313.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_2001313
loop_
_publ_author_name
'Gallucci, J. C.'
'Sharma, P. K.'
'Black, S. D.'
'Rinderle, S. J.'
'Witiak, D. T.'
_publ_section_title
;Structure of
 6-fluoro-1,2,3,4,7,12-hexahydro-7-methyl-12-methylenebenz[<i>a</i>]anthracene
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1868
_journal_page_last               1871
_journal_paper_doi               10.1107/S0108270193003713
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C20 H19 F'
_chemical_formula_weight         278.37
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source
'Cromer & Waber (1974) (C and F); Stewart, Davidson & Simpson (1965) (H)'
_cell_angle_alpha                108.420(10)
_cell_angle_beta                 93.980(10)
_cell_angle_gamma                98.900(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3150(10)
_cell_length_b                   11.1620(10)
_cell_length_c                   7.6570(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      15
_cell_measurement_theta_min      12
_cell_volume                     740.28(15)
_diffrn_measurement_device       'Rigaku AFC-5S'
_diffrn_measurement_method       \q-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3592
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        'average decrease of 1.1% based on intensity'
_diffrn_standards_interval_count 150
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_description       chunk
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       5.1E-6(5)
_refine_ls_extinction_method     'secondary extinction (Zachariasen, 1963)'
_refine_ls_goodness_of_fit_obs   1.44
_refine_ls_hydrogen_treatment    'see below'
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1749
_refine_ls_R_factor_obs          0.041
_refine_ls_shift/esd_max         0.01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/\s^2^(F~o~)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          1749
_reflns_number_total             3384
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            gr1009.cif
_cod_data_source_block           gr1009_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F~o~)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F~o~)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        740.2(2)
_cod_original_formula_sum        'C20 H19 F1'
_cod_database_code               2001313
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
F .2936(2) .42660(10) .4855(2)
C(1) .3927(2) .2023(2) 1.0374(3)
C(2) .5464(3) .1718(2) 1.0440(4)
C(3) .6579(3) .2916(3) 1.0719(4)
C(4A) .4814(2) .3288(2) .8346(3)
C(4) .6393(3) .3373(2) .9080(4)
C(5) .4558(3) .3815(2) .6951(4)
C(6A) .1943(2) .3178(2) .6811(3)
C(6) .3155(3) .3740(2) .6230(3)
C(7A) -.0628(2) .1969(2) .5950(3)
C(7) .0410(2) .3155(2) .5975(3)
C(8) -.1845(3) .1432(3) .4609(3)
C(9) -.2832(3) .0391(3) .4650(4)
C(10) -.2614(3) -.0138(2) .6030(4)
C(11A) -.0418(2) .1452(2) .7362(3)
C(11) -.1414(3) .0382(2) .7369(4)
C(12A) .2183(2) .2666(2) .8229(3)
C(12B) .3627(2) .2692(2) .8982(3)
C(12) .0844(2) .2080(2) .8836(3)
C(13) -.0141(3) .4379(2) .7028(4)
C(14) .0704(3) .2178(3) 1.0587(4)
H(1) .5382 .4236 .6494
H(2) -.2000 .1801 .3622
H(3) -.3688 .0025 .3702
H(4) -.3313 -.0883 .6058
H(5) -.1259 -.0003 .8336
H(6) .3804 .2582 1.1609
H(7) .3217 .1216 1.0039
H(8) .5639 .1394 1.1471
H(9) .5555 .1062 .9270
H(10) .6443 .3590 1.1846
H(11) .7566 .2727 1.0849
H(12) .6858 .2849 .8077
H(13) .6889 .4273 .9453
H(14) -.026(2) .183(2) 1.093(3)
H(15) .149(3) .264(2) 1.160(3)
H(16) .0452 .3131 .4690
H(17) -.0233 .4404 .8306
H(18) -.1099 .4378 .6411
H(19) .0557 .5135 .7040
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
C(2) C(1) C(12B) 113.1(2) yes
C(1) C(2) C(3) 109.8(2) yes
C(2) C(3) C(4) 110.1(2) yes
C(4) C(4A) C(5) 117.6(2) yes
C(4) C(4A) C(12B) 122.9(2) yes
C(5) C(4A) C(12B) 119.5(2) yes
C(3) C(4) C(4A) 114.4(2) yes
C(4A) C(5) C(6) 119.5(2) yes
C(6) C(6A) C(7) 120.9(2) yes
C(6) C(6A) C(12A) 117.4(2) yes
C(7) C(6A) C(12A) 121.7(2) yes
F C(6) C(5) 118.2(2) yes
F C(6) C(6A) 118.1(2) yes
C(5) C(6) C(6A) 123.7(2) yes
C(7) C(7A) C(8) 121.1(2) yes
C(7) C(7A) C(11A) 119.3(2) yes
C(8) C(7A) C(11A) 119.4(2) yes
C(6A) C(7) C(7A) 111.0(2) yes
C(6A) C(7) C(13) 110.6(2) yes
C(7A) C(7) C(13) 111.0(2) yes
C(7A) C(8) C(9) 120.9(2) yes
C(8) C(9) C(10) 119.9(2) yes
C(9) C(10) C(11) 120.0(2) yes
C(7A) C(11A) C(11) 119.1(2) yes
C(7A) C(11A) C(12) 118.7(2) yes
C(11) C(11A) C(12) 122.2(2) yes
C(10) C(11) C(11A) 120.8(2) yes
C(6A) C(12A) C(12B) 120.7(2) yes
C(6A) C(12A) C(12) 115.8(2) yes
C(12B) C(12A) C(12) 123.4(2) yes
C(1) C(12B) C(4A) 118.8(2) yes
C(1) C(12B) C(12A) 122.0(2) yes
C(4A) C(12B) C(12A) 119.1(2) yes
C(11A) C(12) C(12A) 115.6(2) yes
C(11A) C(12) C(14) 120.3(2) yes
C(12A) C(12) C(14) 123.9(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F C(6) 1.376(3) yes
C(1) C(2) 1.523(3) yes
C(1) C(12B) 1.516(3) yes
C(2) C(3) 1.507(4) yes
C(3) C(4) 1.506(4) yes
C(4A) C(4) 1.516(3) yes
C(4A) C(5) 1.396(3) yes
C(4A) C(12B) 1.398(3) yes
C(5) C(6) 1.363(3) yes
C(6A) C(6) 1.376(3) yes
C(6A) C(7) 1.516(3) yes
C(6A) C(12A) 1.398(3) yes
C(7A) C(7) 1.507(3) yes
C(7A) C(8) 1.392(3) yes
C(7A) C(11A) 1.393(3) yes
C(7) C(13) 1.536(3) yes
C(8) C(9) 1.377(4) yes
C(9) C(10) 1.381(4) yes
C(10) C(11) 1.379(3) yes
C(11A) C(11) 1.396(3) yes
C(11A) C(12) 1.486(3) yes
C(12A) C(12B) 1.419(3) yes
C(12A) C(12) 1.490(3) yes
C(12) C(14) 1.328(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139053727
