#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012007.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_2012007
loop_
_publ_author_name
'McElroy, Liam'
'Nieuwenhuyzen, Mark'
'Saunders, Graham C.'
_publ_section_title
cis-Tetracarbonyl[(4-fluorophenyl)diphenylphosphine-P](piperidine-N)molybdenum(0)
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              678
_journal_page_last               679
_journal_paper_doi               10.1107/S0108270101003614
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '[Mo (C18 H14 F1) (C5 H11 N1) (C1 O1)4]'
_chemical_formula_moiety         'C27 H25 F Mo N O4 P'
_chemical_formula_sum            'C27 H25 F Mo N O4 P'
_chemical_formula_weight         573.39
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.598(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.601(3)
_cell_length_b                   10.981(3)
_cell_length_c                   17.973(4)
_cell_measurement_reflns_used    6006
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     2619.7(11)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     .71073
_diffrn_reflns_av_R_equivalents  .048
_diffrn_reflns_av_sigmaI/netI    .045
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12823
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.16
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    .601
_exptl_absorpt_correction_T_max  .899
_exptl_absorpt_correction_T_min  .831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .18
_refine_diff_density_max         .33
_refine_diff_density_min         -.21
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .27(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          .0392
_refine_ls_R_factor_gt           .0331
_refine_ls_shift/su_max          .004
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0352P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0675
_reflns_number_gt                4121
_reflns_number_total             4597
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1444.cif
_cod_data_source_block           I
_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 2.4.1 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 'Monoclinic' changed to 'monoclinic'
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 

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        2619.9(11)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2012007
_cod_database_fobs_code          2012007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Mo1 .482828(19) .18247(3) .220565(14) .04238(9) Uani d . 1 . . Mo
P1 .36045(7) .26762(8) .29794(5) .0446(2) Uani d . 1 . . P
C11A .2316(3) .2621(3) .2411(2) .0487(9) Uani d . 1 . . C
C12A .1603(2) .1838(6) .25977(19) .0601(8) Uani d . 1 B . C
H12A .1747 .1429 .3062 .072 Uiso calc R 1 . . H
C13A .0679(3) .1659(7) .2099(3) .0784(15) Uani d . 1 . . C
H13A .0207 .1131 .2227 .094 Uiso calc R 1 A 1 H
C14A .0467(4) .2262(5) .1420(3) .0781(15) Uani d P .412(7) B 2 C
F14A -.0423(5) .2111(8) .0934(5) .117(4) Uani d P .412(7) B 2 F
C14D .0467(4) .2262(5) .1420(3) .0781(15) Uani d P .588(7) B 1 C
H14D -.0149 .2129 .1086 .094 Uiso calc PR .588(7) B 1 H
C15A .1125(4) .3041(5) .1222(3) .0714(12) Uani d . 1 . . C
H15A .0955 .3462 .0763 .086 Uiso calc R 1 B 1 H
C16A .2049(3) .3217(4) .1699(2) .0596(10) Uani d . 1 B . C
H16A .2510 .3740 .1551 .072 Uiso calc R 1 . . H
C11B .3872(3) .4276(3) .3255(2) .0483(9) Uani d . 1 . . C
C12B .4774(3) .4489(4) .3787(2) .0633(11) Uani d . 1 B . C
H12B .5187 .3838 .3984 .076 Uiso calc R 1 . . H
C13B .5055(4) .5663(5) .4021(3) .0782(15) Uani d . 1 . . C
H13B .5661 .5801 .4367 .094 Uiso calc R 1 B 1 H
C14B .4440(5) .6623(5) .3743(3) .0847(16) Uani d P .412(7) B 2 C
H14B .4621 .7410 .3911 .102 Uiso calc PR .412(7) B 2 H
C14E .4440(5) .6623(5) .3743(3) .0847(16) Uani d P .588(7) B 1 C
F14E .4692(5) .7723(5) .4014(4) .118(3) Uani d P .588(7) B 1 F
C15B .3572(4) .6430(4) .3225(3) .0801(15) Uani d . 1 . . C
H15B .3165 .7089 .3033 .096 Uiso calc R 1 B 1 H
C16B .3280(3) .5266(4) .2976(2) .0602(11) Uani d . 1 B . C
H16B .2681 .5150 .2618 .072 Uiso calc R 1 . . H
C11C .3441(3) .2047(4) .38868(19) .0501(10) Uani d . 1 . . C
C12C .2965(4) .2711(4) .4358(2) .0726(12) Uani d . 1 . . C
H12C .2761 .3506 .4227 .087 Uiso calc R 1 . . H
C13C .2787(5) .2203(5) .5026(3) .0829(17) Uani d . 1 . . C
H13C .2459 .2654 .5337 .100 Uiso calc R 1 . . H
C14C .3093(4) .1055(6) .5221(3) .0836(17) Uani d . 1 . . C
H14C .2976 .0724 .5670 .100 Uiso calc R 1 . . H
C15C .3568(4) .0374(5) .4774(3) .0949(17) Uani d . 1 . . C
H15C .3769 -.0418 .4915 .114 Uiso calc R 1 . . H
C16C .3752(4) .0878(5) .4098(3) .0744(13) Uani d . 1 . . C
H16C .4085 .0421 .3793 .089 Uiso calc R 1 . . H
C1 .5372(3) .0343(4) .2864(2) .0529(10) Uani d . 1 . . C
O1 .5756(3) -.0456(3) .32094(18) .0788(9) Uani d . 1 . . O
C2 .5693(3) .1307(3) .1515(2) .0535(9) Uani d . 1 . . C
O2 .6223(3) .1050(3) .11212(19) .0812(9) Uani d . 1 . . O
C3 .5951(3) .2785(4) .2782(2) .0515(9) Uani d . 1 . . C
O3 .6625(2) .3375(3) .30974(17) .0731(8) Uani d . 1 . . O
C4 .4545(3) .3324(4) .1538(2) .0569(10) Uani d . 1 . . C
O4 .4483(3) .4191(3) .11827(19) .0900(11) Uani d . 1 . . O
N21 .3457(2) .0726(3) .15121(16) .0487(7) Uani d . 1 . . N
H21 .2903 .1147 .1571 .058 Uiso calc R 1 . . H
C22 .3322(4) -.0510(4) .1790(2) .0746(13) Uani d . 1 . . C
H22A .3323 -.0471 .2329 .089 Uiso calc R 1 . . H
H22B .3889 -.1010 .1731 .089 Uiso calc R 1 . . H
C23 .2359(4) -.1108(5) .1375(3) .0928(17) Uani d . 1 . . C
H23A .2335 -.1935 .1560 .111 Uiso calc R 1 . . H
H23B .1789 -.0669 .1486 .111 Uiso calc R 1 . . H
C24 .2270(4) -.1135(5) .0523(2) .0797(14) Uani d . 1 . . C
H24A .2774 -.1679 .0401 .096 Uiso calc R 1 . . H
H24B .1610 -.1435 .0273 .096 Uiso calc R 1 . . H
C25 .2419(4) .0114(5) .0248(2) .0840(15) Uani d . 1 . . C
H25A .1854 .0621 .0301 .101 Uiso calc R 1 . . H
H25B .2433 .0080 -.0289 .101 Uiso calc R 1 . . H
C26 .3388(4) .0686(4) .0686(2) .0771(14) Uani d . 1 . . C
H26A .3954 .0226 .0586 .093 Uiso calc R 1 . . H
H26B .3436 .1509 .0501 .093 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 .6857 '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
C1 Mo1 C2 86.87(15) y
C1 Mo1 C3 88.88(17) y
C1 Mo1 C4 169.94(17) y
C1 Mo1 N21 92.50(13) y
C1 Mo1 P1 99.85(10) y
C2 Mo1 C3 89.15(16) y
C2 Mo1 C4 85.63(16) y
C2 Mo1 N21 91.80(13) y
C2 Mo1 P1 173.15(12) y
C3 Mo1 C4 84.32(16) y
C3 Mo1 N21 178.36(15) y
C3 Mo1 P1 92.29(12) y
C4 Mo1 N21 94.42(13) y
C4 Mo1 P1 87.85(12) y
N21 Mo1 P1 86.60(8) y
C11A P1 C11C 101.42(17) ?
C11A P1 C11B 106.96(17) ?
C11C P1 C11B 100.14(17) ?
C11A P1 Mo1 109.93(11) ?
C11C P1 Mo1 124.41(13) ?
C11B P1 Mo1 112.32(11) ?
C12A C11A C16A 116.8(3) ?
C12A C11A P1 121.3(3) ?
C16A C11A P1 121.1(3) ?
C13A C12A C11A 120.7(5) ?
C14A C13A C12A 119.6(5) ?
F14A C14A C15A 117.7(6) ?
F14A C14A C13A 120.6(6) ?
C15A C14A C13A 121.7(4) ?
C14A C15A C16A 119.8(5) ?
C15A C16A C11A 121.3(4) ?
C16B C11B C12B 118.1(4) ?
C16B C11B P1 126.0(3) ?
C12B C11B P1 115.8(3) ?
C13B C12B C11B 120.4(5) ?
C14B C13B C12B 120.0(5) ?
C15B C14B C13B 120.2(5) ?
C14B C15B C16B 121.0(5) ?
C11B C16B C15B 120.4(4) ?
C16C C11C C12C 118.7(4) ?
C16C C11C P1 120.5(3) ?
C12C C11C P1 120.8(3) ?
C11C C12C C13C 120.7(4) ?
C14C C13C C12C 119.8(5) ?
C13C C14C C15C 121.3(5) ?
C14C C15C C16C 119.4(5) ?
C11C C16C C15C 120.1(5) ?
O1 C1 Mo1 173.6(4) ?
O2 C2 Mo1 177.0(3) ?
O3 C3 Mo1 177.2(3) ?
O4 C4 Mo1 173.4(4) ?
C26 N21 C22 109.2(3) ?
C26 N21 Mo1 115.0(2) ?
C22 N21 Mo1 116.0(2) ?
N21 C22 C23 113.1(4) ?
C24 C23 C22 112.2(4) ?
C25 C24 C23 109.4(4) ?
C24 C25 C26 112.0(4) ?
N21 C26 C25 113.3(4) ?
C26 N21 H21 105.4 ?
C22 N21 H21 105.1 ?
Mo1 N21 H21 105.0 ?
C13A C12A H12A 119.4 ?
C11A C12A H12A 119.9 ?
C13B C12B H12B 119.6 ?
C11B C12B H12B 120.0 ?
C11C C12C H12C 119.9 ?
C13C C12C H12C 119.8 ?
C12A C13A H13A 120.5 ?
C12B C13B H13B 120.2 ?
C14C C13C H13C 120.0 ?
C12C C13C H13C 120.0 ?
C13C C14C H14C 119.4 ?
C15C C14C H14C 119.5 ?
C15B C14E H14B 119.0 ?
C16A C15A H15A 119.9 ?
C16B C15B H15B 119.6 ?
C14C C15C H15C 120.0 ?
C16C C15C H15C 120.5 ?
C15A C16A H16A 119.5 ?
C11A C16A H16A 119.5 ?
C11B C16B H16B 119.9 ?
C15B C16B H16B 119.7 ?
C11C C16C H16C 119.7 ?
C15C C16C H16C 119.8 ?
N21 C22 H22A 109.2 ?
C23 C22 H22A 109.0 ?
N21 C22 H22B 108.8 ?
C23 C22 H22B 109.1 ?
H22A C22 H22B 107.8 ?
C22 C23 H23A 108.9 ?
C24 C23 H23A 109.2 ?
C22 C23 H23B 109.4 ?
C24 C23 H23B 109.3 ?
H23A C23 H23B 107.9 ?
C25 C24 H24A 109.6 ?
C23 C24 H24A 109.9 ?
C25 C24 H24B 110.0 ?
C23 C24 H24B 109.5 ?
H24A C24 H24B 108.3 ?
C24 C25 H25A 108.9 ?
C26 C25 H25A 109.3 ?
C24 C25 H25B 109.3 ?
C26 C25 H25B 109.1 ?
H25A C25 H25B 107.9 ?
N21 C26 H26A 109.2 ?
C25 C26 H26A 109.0 ?
N21 C26 H26B 108.7 ?
C25 C26 H26B 108.8 ?
H26A C26 H26B 107.8 ?
C15B C14B H14B 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mo1 C1 . 2.053(5) y
Mo1 C2 . 1.971(4) y
Mo1 C3 . 1.956(4) y
Mo1 C4 . 2.024(4) y
Mo1 N21 . 2.339(3) y
Mo1 P1 . 2.5670(10) y
P1 C11A . 1.827(4) y
P1 C11B . 1.840(4) y
P1 C11C . 1.829(4) y
C11A C12A . 1.391(6) ?
C11A C16A . 1.411(5) ?
C12A C13A . 1.390(5) ?
C13A C14A . 1.362(8) ?
C14A F14A . 1.339(8) y
C14A C15A . 1.341(7) ?
C15A C16A . 1.373(6) ?
C11B C16B . 1.381(5) ?
C11B C12B . 1.401(5) ?
C12B C13B . 1.384(7) ?
C13B C14B . 1.371(8) ?
C14B C15B . 1.351(7) ?
C15B C16B . 1.384(6) ?
C11C C16C . 1.380(6) ?
C11C C12C . 1.380(5) ?
C12C C13C . 1.392(6) ?
C13C C14C . 1.349(7) ?
C14C C15C . 1.360(8) ?
C15C C16C . 1.407(6) ?
C1 O1 . 1.134(5) y
C2 O2 . 1.150(4) y
C3 O3 . 1.164(4) y
C4 O4 . 1.140(5) y
N21 C26 . 1.467(5) ?
N21 C22 . 1.472(5) ?
C22 C23 . 1.509(6) ?
C23 C24 . 1.508(6) ?
C24 C25 . 1.487(7) ?
C25 C26 . 1.516(6) ?
N21 H21 . .91 ?
C12A H12A . .93 ?
C12B H12B . .93 ?
C12C H12C . .93 ?
C13A H13A . .93 ?
C13B H13B . .93 ?
C13C H13C . .93 ?
C14C H14C . .93 ?
C14E H14B . .93 ?
C15A H15A . .93 ?
C15B H15B . .93 ?
C15C H15C . .93 ?
C16A H16A . .93 ?
C16B H16B . .93 ?
C16C H16C . .93 ?
C22 H22A . .97 ?
C22 H22B . .97 ?
C23 H23A . .97 ?
C23 H23B . .97 ?
C24 H24A . .97 ?
C24 H24B . .97 ?
C25 H25A . .97 ?
C25 H25B . .97 ?
C26 H26A . .97 ?
C26 H26B . .97 ?
C14A H14D . .93 ?
C14B H14B . .93 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N21 H21 C11a 1_555 .91 2.46 3.231(4) 142 yes
N21 H21 C16a 1_555 .91 2.59 3.398(5) 148 yes
C14C H14C O1 2_656 .93 2.68 3.352(6) 130 yes
C13C H13C O3 2_656 .93 2.93 3.535(6) 124 yes
C23 H23A O2 3_445 .97 2.70 3.467(6) 137 yes
C24 H24B O4 4_545 .97 2.80 3.468(6) 127 yes
C24 H24A F14A 3_545 .97 2.77 3.618(9) 146 yes
