#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/53/2005377.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_2005377
loop_
_publ_author_name
'Steiner, Th.'
_publ_section_title
;
 17α-Ethynyl-19-nor-3-oxo-4-androsten-17β-yl Acetate (Norethindrone
 Acetate)
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2261
_journal_page_last               2263
_journal_paper_doi               10.1107/S0108270196002417
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C22 H28 O3'
_chemical_formula_weight         340.5
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           'SHELXL93 (Sheldrick, 1993)'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8302(8)
_cell_length_b                   12.164(1)
_cell_length_c                   23.846(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      7.5
_cell_volume                     1981.2(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device       'Enraf-Nonius Turbo CAD-4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.010
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            1765
_diffrn_reflns_theta_max         59.8
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.14
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.09
_refine_ls_hydrogen_treatment    'H atoms see text'
_refine_ls_number_parameters     255
_refine_ls_number_reflns         1704
_refine_ls_R_factor_obs          0.059
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;                    1/[\s^2^(F^2^)+(0.0796P)^2^+1.1716P] where
P = (F~o~^2^+2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.156
_reflns_number_observed          1437
_reflns_number_total             1704
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ka1177.cif
_cod_data_source_block           ka1177a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_cell_measurement_temperature' value 'room' was changed to '295(2)'
- the room/ambient temperature average [293;298] in Kelvins(K) was
taken.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_cell_measurement_temperature' value 'room' was changed to '295(2)'
- the room/ambient temperature average [293;298] in Kelvins(K) was
taken.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2005377
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(3) .8519(8) .6463(4) .4845(2) .119(2)
O(17) .1844(6) .7420(3) .8955(1) .066(1)
C(1) .7584(9) .7448(5) .6246(2) .070(2)
C(2) .8118(9) .7629(5) .5633(2) .073(2)
C(3) .7622(9) .6662(5) .5283(2) .074(2)
C(4) .5980(10) .5982(4) .5451(2) .076(2)
C(5) .4884(8) .6219(4) .5905(2) .058(1)
C(6) .2964(9) .5658(5) .5992(2) .072(2)
C(7) .2558(9) .5362(4) .6604(2) .065(1)
C(8) .2861(7) .6357(3) .6989(2) .049(1)
C(9) .4998(8) .6767(3) .6928(2) .050(1)
C(10) .5459(8) .7107(4) .6318(2) .055(1)
C(11) .5488(8) .7697(4) .7343(2) .058(1)
C(12) .4961(8) .7400(4) .7953(2) .059(1)
C(13) .2823(7) .7047(3) .7995(2) .048(1)
C(14) .2456(7) .6074(3) .7602(2) .050(1)
C(15) .0456(9) .5643(5) .7768(2) .070(2)
C(16) .0322(8) .5867(5) .8414(2) .066(1)
C(17) .2196(8) .6520(4) .8564(2) .054(1)
C(18) .1453(9) .8021(4) .7877(2) .070(2)
C(20) .3704(9) .5805(4) .8796(2) .059(1)
C(21) .4927(10) .5237(4) .8987(2) .069(2)
C(22) .1072(10) .7199(6) .9466(2) .083(2)
O(22) .0641(8) .6288(4) .9617(2) .107(2)
C(23) .0855(14) .8254(6) .9789(3) .114(3)
H(1A) .8527(9) .6812(5) .6421(2) .079(17)
H(1B) .7844(9) .8204(5) .6480(2) .117(22)
H(2A) .7337(9) .8347(5) .5475(2) .073(15)
H(2B) .9682(9) .7794(5) .5600(2) .114(22)
H(4) .5621(10) .5257(4) .5202(2) .104(20)
H(6A) .2931(9) .4909(5) .5742(2) .097(18)
H(6B) .1798(9) .6194(5) .5842(2) .078(16)
H(7A) .3535(9) .4700(4) .6733(2) .058(13)
H(7B) .1057(9) .5070(4) .6645(2) .069(15)
H(8) .1869(7) .7011(3) .6860(2) .034(10)
H(9) .5952(8) .6076(3) .7029(2) .039(10)
H(10) .4564(8) .7826(4) .6224(2) .048(11)
H(11A) .7049(8) .7879(4) .7319(2) .075(16)
H(11B) .4692(8) .8436(4) .7222(2) .090(18)
H(12A) .5902(8) .6733(4) .8097(2) .057(13)
H(12B) .5211(8) .8109(4) .8222(2) .070(14)
H(14) .3509(7) .5440(3) .7718(2) .051(12)
H(15A) .0335(9) .4766(5) .7679(2) .115(23)
H(15B) -.0699(9) .6077(5) .7543(2) .098(20)
H(16A) -.0983(8) .6345(5) .8512(2) .107(21)
H(16B) .0268(8) .5096(5) .8646(2) .068(14)
H(18A) -.0065(9) .7750(4) .7909(2) .118(24)
H(18B) .1726(9) .8335(4) .7456(2) .140(26)
H(18C) .1724(9) .8670(4) .8183(2) .113(22)
H(21) .6060(10) .4710(4) .9164(2) .091(18)
H(10A) .1382(14) .8937(6) .9534(3) .285(71)
H(10B) .1709(14) .8206(6) 1.0174(3) .163(35)
H(10C) -.0682(14) .8383(6) .9892(3) .213(45)
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(22) O(17) C(17) 119.4(4) yes
C(10) C(1) C(2) 112.1(5) yes
C(3) C(2) C(1) 111.7(5) yes
O(3) C(3) C(4) 120.4(6) yes
O(3) C(3) C(2) 121.2(6) yes
C(4) C(3) C(2) 118.3(5) yes
C(5) C(4) C(3) 122.0(5) yes
C(4) C(5) C(6) 120.1(5) yes
C(4) C(5) C(10) 122.1(5) yes
C(6) C(5) C(10) 117.6(4) yes
C(5) C(6) C(7) 113.6(4) yes
C(6) C(7) C(8) 111.2(4) yes
C(14) C(8) C(7) 111.8(4) yes
C(14) C(8) C(9) 109.5(4) yes
C(7) C(8) C(9) 109.0(4) yes
C(11) C(9) C(10) 111.4(4) yes
C(11) C(9) C(8) 112.4(4) yes
C(10) C(9) C(8) 111.5(4) yes
C(5) C(10) C(1) 111.7(4) yes
C(5) C(10) C(9) 111.6(4) yes
C(1) C(10) C(9) 111.9(4) yes
C(12) C(11) C(9) 112.5(4) yes
C(13) C(12) C(11) 110.6(4) yes
C(12) C(13) C(14) 109.5(4) yes
C(12) C(13) C(18) 110.7(4) yes
C(14) C(13) C(18) 112.7(4) yes
C(12) C(13) C(17) 115.8(4) yes
C(14) C(13) C(17) 99.8(3) yes
C(18) C(13) C(17) 107.9(4) yes
C(15) C(14) C(8) 119.4(4) yes
C(15) C(14) C(13) 104.8(4) yes
C(8) C(14) C(13) 112.4(3) yes
C(14) C(15) C(16) 104.4(4) yes
C(17) C(16) C(15) 105.6(4) yes
C(20) C(17) O(17) 108.7(4) yes
C(20) C(17) C(16) 111.5(4) yes
O(17) C(17) C(16) 113.4(4) yes
C(20) C(17) C(13) 112.4(4) yes
O(17) C(17) C(13) 107.1(3) yes
C(16) C(17) C(13) 103.6(4) yes
C(21) C(20) C(17) 179.4(5) yes
O(22) C(22) O(17) 123.2(5) yes
O(22) C(22) C(23) 127.6(6) yes
O(17) C(22) C(23) 109.2(6) yes
C(10) C(1) H(1A) 109.2(3) no
C(2) C(1) H(1A) 109.2(3) no
C(10) C(1) H(1B) 109.2(3) no
C(2) C(1) H(1B) 109.2(3) no
H(1A) C(1) H(1B) 107.9 no
C(3) C(2) H(2A) 109.3(3) no
C(1) C(2) H(2A) 109.3(3) no
C(3) C(2) H(2B) 109.3(3) no
C(1) C(2) H(2B) 109.3(3) no
H(2A) C(2) H(2B) 107.9 no
C(5) C(4) H(4) 119.0(3) no
C(3) C(4) H(4) 119.0(3) no
C(5) C(6) H(6A) 108.9(3) no
C(7) C(6) H(6A) 108.9(3) no
C(5) C(6) H(6B) 108.9(3) no
C(7) C(6) H(6B) 108.9(3) no
H(6A) C(6) H(6B) 107.7 no
C(6) C(7) H(7A) 109.4(3) no
C(8) C(7) H(7A) 109.4(3) no
C(6) C(7) H(7B) 109.4(3) no
C(8) C(7) H(7B) 109.4(3) no
H(7A) C(7) H(7B) 108.0 no
C(14) C(8) H(8) 108.9(2) no
C(7) C(8) H(8) 108.9(3) no
C(9) C(8) H(8) 108.9(2) no
C(11) C(9) H(9) 107.1(3) no
C(10) C(9) H(9) 107.1(3) no
C(8) C(9) H(9) 107.1(2) no
C(5) C(10) H(10) 107.1(3) no
C(1) C(10) H(10) 107.1(3) no
C(9) C(10) H(10) 107.1(3) no
C(12) C(11) H(11A) 109.1(3) no
C(9) C(11) H(11A) 109.1(3) no
C(12) C(11) H(11B) 109.1(3) no
C(9) C(11) H(11B) 109.1(3) no
H(11A) C(11) H(11B) 107.8 no
C(13) C(12) H(12A) 109.5(2) no
C(11) C(12) H(12A) 109.5(3) no
C(13) C(12) H(12B) 109.5(2) no
C(11) C(12) H(12B) 109.5(2) no
H(12A) C(12) H(12B) 108.1 no
C(15) C(14) H(14) 106.5(3) no
C(8) C(14) H(14) 106.5(3) no
C(13) C(14) H(14) 106.5(2) no
C(14) C(15) H(15A) 110.9(3) no
C(16) C(15) H(15A) 110.9(3) no
C(14) C(15) H(15B) 110.9(3) no
C(16) C(15) H(15B) 110.9(3) no
H(15A) C(15) H(15B) 108.9 no
C(17) C(16) H(16A) 110.6(3) no
C(15) C(16) H(16A) 110.6(3) no
C(17) C(16) H(16B) 110.6(3) no
C(15) C(16) H(16B) 110.6(3) no
H(16A) C(16) H(16B) 108.8 no
C(13) C(18) H(18A) 109.5(3) no
C(13) C(18) H(18B) 109.5(3) no
H(18A) C(18) H(18B) 109.5 no
C(13) C(18) H(18C) 109.5(3) no
H(18A) C(18) H(18C) 109.5 no
H(18B) C(18) H(18C) 109.5 no
C(22) C(23) H(10A) 109.5(4) no
C(22) C(23) H(10B) 109.5(4) no
H(10A) C(23) H(10B) 109.5 no
C(22) C(23) H(10C) 109.5(4) no
H(10A) C(23) H(10C) 109.5 no
H(10B) C(23) H(10C) 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(3) C(3) 1.234(6) yes
O(17) C(22) 1.355(7) yes
O(17) C(17) 1.458(5) yes
C(1) C(10) 1.519(8) yes
C(1) C(2) 1.524(7) yes
C(2) C(3) 1.482(7) yes
C(3) C(4) 1.450(8) yes
C(4) C(5) 1.348(7) yes
C(5) C(6) 1.493(8) yes
C(5) C(10) 1.513(6) yes
C(6) C(7) 1.528(7) yes
C(7) C(8) 1.532(6) yes
C(8) C(14) 1.526(6) yes
C(8) C(9) 1.550(7) yes
C(9) C(11) 1.541(6) yes
C(9) C(10) 1.545(6) yes
C(11) C(12) 1.540(6) yes
C(12) C(13) 1.526(7) yes
C(13) C(14) 1.530(6) yes
C(13) C(18) 1.536(6) yes
C(13) C(17) 1.561(6) yes
C(14) C(15) 1.515(8) yes
C(15) C(16) 1.567(7) yes
C(16) C(17) 1.549(7) yes
C(17) C(20) 1.457(8) yes
C(20) C(21) 1.176(7) yes
O(22) C(22) 1.202(7) yes
C(22) C(23) 1.503(8) yes
C(1) H(1A) 1.09 no
C(1) H(1B) 1.09 no
C(2) H(2A) 1.09 no
C(2) H(2B) 1.09 no
C(4) H(4) 1.09 no
C(6) H(6A) 1.09 no
C(6) H(6B) 1.09 no
C(7) H(7A) 1.09 no
C(7) H(7B) 1.09 no
C(8) H(8) 1.09 no
C(9) H(9) 1.09 no
C(10) H(10) 1.09 no
C(11) H(11A) 1.09 no
C(11) H(11B) 1.09 no
C(12) H(12A) 1.09 no
C(12) H(12B) 1.09 no
C(14) H(14) 1.09 no
C(15) H(15A) 1.09 no
C(15) H(15B) 1.09 no
C(16) H(16A) 1.09 no
C(16) H(16B) 1.09 no
C(18) H(18A) 1.09 no
C(18) H(18B) 1.09 no
C(18) H(18C) 1.09 no
C(21) H(21) 1.09 no
C(23) H(10A) 1.09 no
C(23) H(10B) 1.09 no
C(23) H(10C) 1.09 no
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
_geom_torsion_publ_flag
C(13) C(17) O(17) C(22) 172.9(5) yes
C(16) C(17) O(17) C(22) 59.2(6) yes
C(17) O(17) C(22) O(22) -0.6(9) yes
C(17) O(17) C(22) C(23) 179.9(5) yes
