#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/39/1503959.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_1503959
loop_
_publ_author_name
'Wen, Yuehong'
'Zhao, Baoguo'
'Shi, Yian'
_publ_section_title
;
 Cu(I)-catalyzed diamination of disubstituted terminal olefins: an
 approach to potent NK1 antagonist.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2365
_journal_page_last               2368
_journal_paper_doi               10.1021/ol900808z
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_sum            'C31 H30 F6 N2 O3'
_chemical_formula_weight         592.57
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'XCIF, Bruker, 2008'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.057(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5388(6)
_cell_length_b                   14.5600(10)
_cell_length_c                   10.9484(7)
_cell_measurement_reflns_used    7564
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.04
_cell_measurement_theta_min      2.41
_cell_volume                     1437.23(17)
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'APEX2 (Bruker, 2009)'
_computing_publication_material  'APEX2 (Bruker, 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.1060
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40750
_diffrn_reflns_theta_full        45.37
_diffrn_reflns_theta_max         45.37
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.0167(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         18762
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                10041
_reflns_number_total             18762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900808z_si_002.cif
_cod_data_source_block           ys190_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1437.23(16)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1503959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.68124(11) 0.78665(7) 1.08382(10) 0.01585(17) Uani 1 1 d . A .
N2 N 0.47842(11) 0.78631(7) 1.14398(10) 0.01760(18) Uani 1 1 d . A .
O1 O 0.48673(9) 0.86595(6) 0.87187(8) 0.01856(16) Uani 1 1 d . A .
O2 O 0.54655(11) 0.65049(7) 1.06753(11) 0.0260(2) Uani 1 1 d . A .
O3 O 0.84430(11) 0.80442(7) 0.97339(10) 0.02372(19) Uani 1 1 d . A .
F1 F 0.85407(11) 0.75933(8) 0.67996(10) 0.0404(2) Uani 1 1 d . . .
F2 F 0.76224(11) 0.75632(8) 0.47306(10) 0.0409(2) Uani 1 1 d . . .
F3 F 0.92550(10) 0.85666(8) 0.56559(11) 0.0413(2) Uani 1 1 d . . .
F4 F 0.4655(10) 1.0724(3) 0.2884(3) 0.101(2) Uani 0.492(4) 1 d P A 1
F4A F 0.5660(6) 1.0935(3) 0.3193(5) 0.0657(15) Uani 0.508(4) 1 d P A 2
F5 F 0.3541(3) 1.0963(4) 0.3402(5) 0.0828(19) Uani 0.492(4) 1 d P A 1
F5A F 0.4215(7) 1.1504(3) 0.4334(5) 0.078(2) Uani 0.508(4) 1 d P A 2
F6 F 0.6357(4) 1.1405(3) 0.4242(6) 0.0980(18) Uani 0.492(4) 1 d P A 1
F6A F 0.5309(7) 1.17129(19) 0.4641(3) 0.0809(19) Uani 0.508(4) 1 d P A 2
C1 C 0.80627(15) 0.81227(10) 0.57556(14) 0.0248(3) Uani 1 1 d . . .
C2 C 0.5041(2) 1.09224(11) 0.40625(16) 0.0343(3) Uani 1 1 d . . .
C3 C 0.60655(14) 0.86243(9) 0.66361(12) 0.0199(2) Uani 1 1 d . . .
H3A H 0.6297 0.8114 0.7208 0.024 Uiso 1 1 calc R . .
C4 C 0.68695(13) 0.87786(9) 0.57986(12) 0.0196(2) Uani 1 1 d . A .
C5 C 0.65579(15) 0.95270(9) 0.49583(13) 0.0218(2) Uani 1 1 d . . .
H5A H 0.7122 0.9635 0.4400 0.026 Uiso 1 1 calc R A .
C6 C 0.54062(15) 1.01108(9) 0.49546(13) 0.0224(2) Uani 1 1 d . A .
C7 C 0.45891(15) 0.99612(10) 0.57841(13) 0.0217(2) Uani 1 1 d . . .
H7A H 0.3803 1.0367 0.5769 0.026 Uiso 1 1 calc R A .
C8 C 0.49186(14) 0.92213(9) 0.66334(12) 0.0187(2) Uani 1 1 d . A .
C9 C 0.40063(14) 0.90580(9) 0.75248(12) 0.0202(2) Uani 1 1 d . . .
H9A H 0.3584 0.9655 0.7693 0.024 Uiso 1 1 calc R A .
C10 C 0.27491(16) 0.83852(13) 0.69190(14) 0.0295(3) Uani 1 1 d . A .
H10A H 0.2176 0.8291 0.7506 0.044 Uiso 1 1 calc R . .
H10B H 0.3162 0.7797 0.6764 0.044 Uiso 1 1 calc R . .
H10C H 0.2100 0.8634 0.6097 0.044 Uiso 1 1 calc R . .
C11 C 0.59523(13) 0.92761(8) 0.95149(11) 0.0173(2) Uani 1 1 d . . .
H11A H 0.5509 0.9889 0.9533 0.021 Uiso 1 1 calc R A .
H11B H 0.6792 0.9345 0.9179 0.021 Uiso 1 1 calc R . .
C12 C 0.64849(12) 0.88540(8) 1.08743(11) 0.01569(19) Uani 1 1 d . A .
C13 C 0.51794(13) 0.88297(8) 1.14267(12) 0.0180(2) Uani 1 1 d . . .
H13A H 0.5488 0.9088 1.2311 0.022 Uiso 1 1 calc R A .
H13B H 0.4327 0.9189 1.0873 0.022 Uiso 1 1 calc R . .
C14 C 0.32901(14) 0.76035(9) 1.14888(13) 0.0213(2) Uani 1 1 d . . .
C15 C 0.21785(16) 0.76797(12) 1.01304(17) 0.0330(3) Uani 1 1 d . A .
H15A H 0.2184 0.8308 0.9811 0.049 Uiso 1 1 calc R . .
H15B H 0.1184 0.7530 1.0149 0.049 Uiso 1 1 calc R . .
H15C H 0.2452 0.7250 0.9557 0.049 Uiso 1 1 calc R . .
C16 C 0.28871(18) 0.82743(12) 1.24017(17) 0.0328(3) Uani 1 1 d . A .
H16A H 0.2876 0.8902 1.2077 0.049 Uiso 1 1 calc R . .
H16B H 0.3624 0.8228 1.3267 0.049 Uiso 1 1 calc R . .
H16C H 0.1904 0.8121 1.2445 0.049 Uiso 1 1 calc R . .
C17 C 0.33012(19) 0.66312(12) 1.20165(19) 0.0366(4) Uani 1 1 d . A .
H17A H 0.3556 0.6193 1.1442 0.055 Uiso 1 1 calc R . .
H17B H 0.2317 0.6484 1.2063 0.055 Uiso 1 1 calc R . .
H17C H 0.4038 0.6592 1.2882 0.055 Uiso 1 1 calc R . .
C18 C 0.56350(13) 0.73148(8) 1.09646(12) 0.0177(2) Uani 1 1 d . . .
C19 C 0.78912(13) 0.75392(8) 1.03443(12) 0.0175(2) Uani 1 1 d . . .
C20 C 0.84641(13) 0.65859(8) 1.06889(12) 0.0184(2) Uani 1 1 d . A .
C21 C 0.87390(15) 0.62329(10) 1.19336(13) 0.0227(2) Uani 1 1 d . . .
H21A H 0.8442 0.6569 1.2551 0.027 Uiso 1 1 calc R A .
C22 C 0.94461(16) 0.53904(10) 1.22684(15) 0.0279(3) Uani 1 1 d . A .
H22A H 0.9651 0.5159 1.3120 0.033 Uiso 1 1 calc R . .
C23 C 0.98541(16) 0.48845(10) 1.13609(17) 0.0301(3) Uani 1 1 d . . .
H23A H 1.0324 0.4305 1.1589 0.036 Uiso 1 1 calc R A .
C24 C 0.95742(16) 0.52272(10) 1.01230(16) 0.0283(3) Uani 1 1 d . A .
H24A H 0.9840 0.4878 0.9499 0.034 Uiso 1 1 calc R . .
C25 C 0.89033(15) 0.60840(10) 0.97918(14) 0.0235(2) Uani 1 1 d . . .
H25A H 0.8745 0.6326 0.8952 0.028 Uiso 1 1 calc R A .
C26 C 0.77837(13) 0.94058(8) 1.17538(11) 0.0166(2) Uani 1 1 d . . .
C27 C 0.90562(15) 0.89852(9) 1.25886(12) 0.0215(2) Uani 1 1 d . A .
H27A H 0.9142 0.8335 1.2601 0.026 Uiso 1 1 calc R . .
C28 C 1.01944(16) 0.95136(10) 1.33988(13) 0.0252(3) Uani 1 1 d . . .
H28A H 1.1058 0.9221 1.3954 0.030 Uiso 1 1 calc R A .
C29 C 1.00868(16) 1.04609(11) 1.34080(14) 0.0270(3) Uani 1 1 d . A .
H29A H 1.0870 1.0818 1.3966 0.032 Uiso 1 1 calc R . .
C30 C 0.88260(17) 1.08839(10) 1.25953(15) 0.0292(3) Uani 1 1 d . . .
H30A H 0.8740 1.1534 1.2601 0.035 Uiso 1 1 calc R A .
C31 C 0.76861(15) 1.03625(9) 1.17713(14) 0.0240(2) Uani 1 1 d . A .
H31A H 0.6830 1.0660 1.1213 0.029 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
C19 N1 C18 123.41(10)
C19 N1 C12 122.25(10)
C18 N1 C12 111.52(9)
C18 N2 C13 112.02(9)
C18 N2 C14 124.22(11)
C13 N2 C14 119.86(10)
C9 O1 C11 112.95(10)
F1 C1 F2 107.07(13)
F1 C1 F3 106.68(12)
F2 C1 F3 105.49(11)
F1 C1 C4 113.16(11)
F2 C1 C4 112.38(12)
F3 C1 C4 111.58(12)
F4 C2 F5A 113.7(4)
F4 C2 F4A 44.5(3)
F5A C2 F4A 130.3(2)
F4 C2 F6A 130.6(3)
F5A C2 F6A 47.6(3)
F4A C2 F6A 106.6(3)
F4 C2 F5 64.2(5)
F5A C2 F5 58.1(3)
F4A C2 F5 105.3(4)
F6A C2 F5 102.9(4)
F4 C2 F6 102.1(4)
F5A C2 F6 103.4(4)
F4A C2 F6 58.8(3)
F6A C2 F6 57.3(3)
F5 C2 F6 141.7(2)
F4 C2 C6 114.6(2)
F5A C2 C6 114.05(17)
F4A C2 C6 115.60(19)
F6A C2 C6 114.46(18)
F5 C2 C6 110.87(18)
F6 C2 C6 107.33(19)
C4 C3 C8 119.85(12)
C3 C4 C5 121.07(12)
C3 C4 C1 120.35(12)
C5 C4 C1 118.55(11)
C6 C5 C4 118.59(12)
C5 C6 C7 120.86(12)
C5 C6 C2 120.00(12)
C7 C6 C2 119.14(12)
C8 C7 C6 120.30(12)
C7 C8 C3 119.31(11)
C7 C8 C9 119.84(11)
C3 C8 C9 120.83(11)
O1 C9 C10 105.93(11)
O1 C9 C8 111.93(10)
C10 C9 C8 110.78(11)
O1 C11 C12 106.50(9)
N1 C12 C26 113.26(9)
N1 C12 C11 111.73(9)
C26 C12 C11 110.15(9)
N1 C12 C13 101.08(9)
C26 C12 C13 110.82(9)
C11 C12 C13 109.47(9)
N2 C13 C12 105.59(9)
N2 C14 C15 108.36(11)
N2 C14 C17 111.07(11)
C15 C14 C17 110.70(13)
N2 C14 C16 107.92(11)
C15 C14 C16 110.32(13)
C17 C14 C16 108.42(12)
O2 C18 N2 128.60(11)
O2 C18 N1 124.26(11)
N2 C18 N1 107.14(10)
O3 C19 N1 120.72(11)
O3 C19 C20 120.64(10)
N1 C19 C20 118.37(10)
C25 C20 C21 119.34(12)
C25 C20 C19 118.58(11)
C21 C20 C19 121.60(11)
C22 C21 C20 120.10(13)
C21 C22 C23 120.26(14)
C24 C23 C22 119.90(13)
C23 C24 C25 120.11(13)
C20 C25 C24 120.24(13)
C31 C26 C27 118.36(11)
C31 C26 C12 119.32(11)
C27 C26 C12 122.27(11)
C28 C27 C26 120.33(12)
C29 C28 C27 120.84(13)
C28 C29 C30 119.31(13)
C29 C30 C31 120.34(13)
C30 C31 C26 120.81(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C19 1.3936(15)
N1 C18 1.4239(15)
N1 C12 1.4746(15)
N2 C18 1.3574(16)
N2 C13 1.4583(16)
N2 C14 1.4922(15)
O1 C9 1.4208(15)
O1 C11 1.4311(15)
O2 C18 1.2179(16)
O3 C19 1.2223(15)
F1 C1 1.3296(17)
F2 C1 1.3385(17)
F3 C1 1.3433(18)
F4 C2 1.254(4)
F4A C2 1.274(3)
F5 C2 1.377(3)
F5A C2 1.256(3)
F6 C2 1.396(4)
F6A C2 1.298(3)
C1 C4 1.4982(18)
C2 C6 1.500(2)
C3 C4 1.3923(17)
C3 C8 1.3965(18)
C4 C5 1.3941(19)
C5 C6 1.3880(19)
C6 C7 1.3936(18)
C7 C8 1.3904(19)
C8 C9 1.5234(17)
C9 C10 1.523(2)
C11 C12 1.5353(17)
C12 C26 1.5260(17)
C12 C13 1.5522(16)
C14 C15 1.523(2)
C14 C17 1.528(2)
C14 C16 1.533(2)
C19 C20 1.4942(17)
C20 C25 1.3939(17)
C20 C21 1.3989(18)
C21 C22 1.3901(19)
C22 C23 1.391(2)
C23 C24 1.386(2)
C24 C25 1.395(2)
C26 C31 1.3965(18)
C26 C27 1.3997(18)
C27 C28 1.389(2)
C28 C29 1.383(2)
C29 C30 1.385(2)
C30 C31 1.390(2)
