#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:21:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179106 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/68/4306814.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_4306814
loop_
_publ_author_name
'Andrew J. Clulow'
'Jonathan D. Selby'
'Michael G. Cushion'
'Andrew D. Schwarz'
'Philip Mountford'
_publ_contact_author
;
 Prof P. Mountford           
 Chemistry Reaearch Laboratory
 Mansfield Road
 Oxford
 OX1 3TA
 UK
;
_publ_contact_author_email       Philip.Mountford@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 285141'
_publ_contact_author_phone       '+44 1865 285140'
_publ_section_title
;
Synthesis, Structures and Reactivity of Group 4 Hydrazido Complexes
Supported by Calix[4]arene Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12049
_journal_page_last               12062
_journal_paper_doi               10.1021/ic801735c
_journal_volume                  47
_journal_year                    2008
_chemical_compound_source        Aldrich
_chemical_formula_moiety         'C12 H12 N2'
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24
_chemical_name_systematic
;
Ph2NNH2
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                116.1926(11)
_cell_angle_beta                 112.4355(12)
_cell_angle_gamma                94.3481(16)
_cell_formula_units_Z            4
_cell_length_a                   9.5104(2)
_cell_length_b                   11.1230(2)
_cell_length_c                   11.6530(3)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     977.05(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'Nonius (1997-2001). COLLECT.'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7932
_diffrn_reflns_theta_full        25.259
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_min         5.145
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.16
_refine_ls_extinction_coef       200(50)
_refine_ls_extinction_method
'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_ref   1.0967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000166
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.716 0.412 0.368 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0807
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0522
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2808
_reflns_number_total             4382
_reflns_threshold_expression     I>3.00u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.992(3)
_cod_data_source_file            ic801735c_si_001_5.cif
_cod_data_source_block           COMPOUND_Ph2NNH2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4306814
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N -0.0065(2) -0.05256(18) 0.24655(18) 0.0463 1.0000 Uani . . . . . .
N2 N 0.14198(17) 0.00336(14) 0.37224(15) 0.0370 1.0000 Uani . . . . . .
C1 C 0.21433(18) 0.14747(16) 0.43498(16) 0.0292 1.0000 Uani . . . . . .
C2 C 0.38003(19) 0.20126(17) 0.50157(17) 0.0313 1.0000 Uani . . . . . .
C3 C 0.4497(2) 0.34197(18) 0.55909(18) 0.0339 1.0000 Uani . . . . . .
C4 C 0.3570(2) 0.43117(18) 0.54995(19) 0.0376 1.0000 Uani . . . . . .
C5 C 0.1930(2) 0.37770(18) 0.48316(18) 0.0360 1.0000 Uani . . . . . .
C6 C 0.1217(2) 0.23685(17) 0.42603(17) 0.0327 1.0000 Uani . . . . . .
C7 C 0.18580(19) -0.07105(16) 0.44435(18) 0.0313 1.0000 Uani . . . . . .
C8 C 0.1308(2) -0.21837(17) 0.36626(19) 0.0371 1.0000 Uani . . . . . .
C9 C 0.1738(2) -0.29270(18) 0.4374(2) 0.0420 1.0000 Uani . . . . . .
C10 C 0.2696(2) -0.22494(19) 0.5845(2) 0.0412 1.0000 Uani . . . . . .
C11 C 0.3230(2) -0.07917(19) 0.6622(2) 0.0387 1.0000 Uani . . . . . .
C12 C 0.2816(2) -0.00287(17) 0.59413(18) 0.0344 1.0000 Uani . . . . . .
H1 H 0.009(3) -0.117(3) 0.170(3) 0.073(8) 1.0000 Uiso . . . . . .
H2 H -0.089(4) -0.093(3) 0.259(3) 0.081(8) 1.0000 Uiso . . . . . .
H21 H 0.4480 0.1379 0.5081 0.0379 1.0000 Uiso R . . . . .
H31 H 0.5682 0.3801 0.6076 0.0422 1.0000 Uiso R . . . . .
H41 H 0.4078 0.5325 0.5906 0.0483 1.0000 Uiso R . . . . .
H51 H 0.1254 0.4413 0.4765 0.0455 1.0000 Uiso R . . . . .
H61 H 0.0031 0.1993 0.3780 0.0402 1.0000 Uiso R . . . . .
H81 H 0.0613 -0.2693 0.2594 0.0429 1.0000 Uiso R . . . . .
H91 H 0.1338 -0.3974 0.3806 0.0537 1.0000 Uiso R . . . . .
H101 H 0.3003 -0.2794 0.6345 0.0524 1.0000 Uiso R . . . . .
H111 H 0.3924 -0.0286 0.7690 0.0512 1.0000 Uiso R . . . . .
H121 H 0.3207 0.1019 0.6518 0.0425 1.0000 Uiso R . . . . .
N101 N 0.2907(3) 0.36468(19) -0.20263(19) 0.0480 1.0000 Uani . . . . . .
N102 N 0.2619(2) 0.44062(16) -0.08364(15) 0.0402 1.0000 Uani . . . . . .
C101 C 0.25300(18) 0.57785(17) -0.04355(17) 0.0309 1.0000 Uani . . . . . .
C102 C 0.2089(2) 0.61930(19) -0.14650(19) 0.0369 1.0000 Uani . . . . . .
C103 C 0.2054(2) 0.7558(2) -0.1069(2) 0.0432 1.0000 Uani . . . . . .
C104 C 0.2443(2) 0.8537(2) 0.0339(2) 0.0460 1.0000 Uani . . . . . .
C105 C 0.2896(2) 0.81365(18) 0.1366(2) 0.0414 1.0000 Uani . . . . . .
C106 C 0.2949(2) 0.67805(18) 0.09949(18) 0.0343 1.0000 Uani . . . . . .
C107 C 0.27329(19) 0.37909(16) 0.00116(17) 0.0303 1.0000 Uani . . . . . .
C108 C 0.37134(19) 0.29297(17) 0.00959(18) 0.0330 1.0000 Uani . . . . . .
C109 C 0.3782(2) 0.22972(19) 0.0898(2) 0.0398 1.0000 Uani . . . . . .
C110 C 0.2889(2) 0.25046(18) 0.16306(19) 0.0415 1.0000 Uani . . . . . .
C111 C 0.1893(2) 0.33384(18) 0.15288(18) 0.0381 1.0000 Uani . . . . . .
C112 C 0.17950(19) 0.39696(18) 0.07234(18) 0.0342 1.0000 Uani . . . . . .
H3 H 0.194(3) 0.340(2) -0.288(3) 0.058(7) 1.0000 Uiso . . . . . .
H4 H 0.368(3) 0.421(3) -0.203(3) 0.077(8) 1.0000 Uiso . . . . . .
H1021 H 0.1790 0.5495 -0.2490 0.0460 1.0000 Uiso R . . . . .
H1031 H 0.1744 0.7840 -0.1814 0.0527 1.0000 Uiso R . . . . .
H1041 H 0.2399 0.9516 0.0612 0.0569 1.0000 Uiso R . . . . .
H1051 H 0.3187 0.8836 0.2388 0.0493 1.0000 Uiso R . . . . .
H1061 H 0.3286 0.6508 0.1748 0.0397 1.0000 Uiso R . . . . .
H1081 H 0.4371 0.2776 -0.0423 0.0372 1.0000 Uiso R . . . . .
H1091 H 0.4487 0.1678 0.0942 0.0464 1.0000 Uiso R . . . . .
H1101 H 0.2962 0.2059 0.2224 0.0467 1.0000 Uiso R . . . . .
H1111 H 0.1231 0.3487 0.2044 0.0427 1.0000 Uiso R . . . . .
H1121 H 0.1060 0.4560 0.0648 0.0380 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 . N1 . H1 . 105.9(16) no
N2 . N1 . H2 . 110.5(17) no
H1 . N1 . H2 . 114(2) no
N1 . N2 . C1 . 114.19(13) yes
N1 . N2 . C7 . 119.95(14) yes
C1 . N2 . C7 . 123.71(13) yes
N2 . C1 . C2 . 120.51(14) yes
N2 . C1 . C6 . 120.41(14) yes
C2 . C1 . C6 . 119.02(15) yes
C1 . C2 . C3 . 120.09(15) yes
C1 . C2 . H21 . 119.8 no
C3 . C2 . H21 . 120.1 no
C2 . C3 . C4 . 120.86(16) yes
C2 . C3 . H31 . 119.7 no
C4 . C3 . H31 . 119.4 no
C3 . C4 . C5 . 119.03(16) yes
C3 . C4 . H41 . 120.6 no
C5 . C4 . H41 . 120.4 no
C4 . C5 . C6 . 120.67(15) yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 119.8 no
C5 . C6 . C1 . 120.32(15) yes
C5 . C6 . H61 . 120.0 no
C1 . C6 . H61 . 119.7 no
N2 . C7 . C8 . 119.84(15) yes
N2 . C7 . C12 . 121.92(14) yes
C8 . C7 . C12 . 118.23(15) yes
C7 . C8 . C9 . 120.06(17) yes
C7 . C8 . H81 . 119.7 no
C9 . C8 . H81 . 120.3 no
C8 . C9 . C10 . 121.37(16) yes
C8 . C9 . H91 . 119.3 no
C10 . C9 . H91 . 119.3 no
C9 . C10 . C11 . 118.69(17) yes
C9 . C10 . H101 . 120.7 no
C11 . C10 . H101 . 120.6 no
C10 . C11 . C12 . 121.06(17) yes
C10 . C11 . H111 . 119.5 no
C12 . C11 . H111 . 119.4 no
C7 . C12 . C11 . 120.58(15) yes
C7 . C12 . H121 . 119.5 no
C11 . C12 . H121 . 119.9 no
N102 . N101 . H3 . 106.4(14) no
N102 . N101 . H4 . 111.5(17) no
H3 . N101 . H4 . 105(2) no
N101 . N102 . C101 . 119.61(14) yes
N101 . N102 . C107 . 114.86(13) yes
C101 . N102 . C107 . 124.49(13) yes
N102 . C101 . C102 . 119.85(14) yes
N102 . C101 . C106 . 121.77(14) yes
C102 . C101 . C106 . 118.31(15) yes
C101 . C102 . C103 . 120.28(16) yes
C101 . C102 . H1021 . 119.5 no
C103 . C102 . H1021 . 120.2 no
C102 . C103 . C104 . 121.22(17) yes
C102 . C103 . H1031 . 119.4 no
C104 . C103 . H1031 . 119.4 no
C103 . C104 . C105 . 118.76(17) yes
C103 . C104 . H1041 . 120.6 no
C105 . C104 . H1041 . 120.6 no
C104 . C105 . C106 . 120.97(17) yes
C104 . C105 . H1051 . 119.5 no
C106 . C105 . H1051 . 119.5 no
C101 . C106 . C105 . 120.46(16) yes
C101 . C106 . H1061 . 119.4 no
C105 . C106 . H1061 . 120.1 no
N102 . C107 . C108 . 120.65(15) yes
N102 . C107 . C112 . 120.57(15) yes
C108 . C107 . C112 . 118.68(15) yes
C107 . C108 . C109 . 120.26(16) yes
C107 . C108 . H1081 . 119.5 no
C109 . C108 . H1081 . 120.2 no
C108 . C109 . C110 . 120.99(17) yes
C108 . C109 . H1091 . 119.3 no
C110 . C109 . H1091 . 119.7 no
C109 . C110 . C111 . 118.95(16) yes
C109 . C110 . H1101 . 120.5 no
C111 . C110 . H1101 . 120.5 no
C110 . C111 . C112 . 121.00(16) yes
C110 . C111 . H1111 . 119.7 no
C112 . C111 . H1111 . 119.3 no
C107 . C112 . C111 . 120.09(16) yes
C107 . C112 . H1121 . 119.7 no
C111 . C112 . H1121 . 120.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . N2 . 1.418(2) yes
N1 . H1 . 0.94(3) no
N1 . H2 . 0.97(3) no
N2 . C1 . 1.411(2) yes
N2 . C7 . 1.401(2) yes
C1 . C2 . 1.399(2) yes
C1 . C6 . 1.389(2) yes
C2 . C3 . 1.384(2) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.388(2) yes
C3 . H31 . 1.000 no
C4 . C5 . 1.384(3) yes
C4 . H41 . 1.000 no
C5 . C6 . 1.390(2) yes
C5 . H51 . 1.000 no
C6 . H61 . 1.000 no
C7 . C8 . 1.406(2) yes
C7 . C12 . 1.402(2) yes
C8 . C9 . 1.391(3) yes
C8 . H81 . 1.000 no
C9 . C10 . 1.379(3) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.391(3) yes
C10 . H101 . 1.000 no
C11 . C12 . 1.382(2) yes
C11 . H111 . 1.000 no
C12 . H121 . 1.000 no
N101 . N102 . 1.415(2) yes
N101 . H3 . 0.97(3) no
N101 . H4 . 0.94(3) no
N102 . C101 . 1.406(2) yes
N102 . C107 . 1.408(2) yes
C101 . C102 . 1.401(2) yes
C101 . C106 . 1.402(2) yes
C102 . C103 . 1.385(3) yes
C102 . H1021 . 1.000 no
C103 . C104 . 1.383(3) yes
C103 . H1031 . 1.000 no
C104 . C105 . 1.386(3) yes
C104 . H1041 . 1.000 no
C105 . C106 . 1.385(2) yes
C105 . H1051 . 1.000 no
C106 . H1061 . 1.000 no
C107 . C108 . 1.395(2) yes
C107 . C112 . 1.403(2) yes
C108 . C109 . 1.383(2) yes
C108 . H1081 . 1.000 no
C109 . C110 . 1.383(3) yes
C109 . H1091 . 1.000 no
C110 . C111 . 1.385(3) yes
C110 . H1101 . 1.000 no
C111 . C112 . 1.381(3) yes
C111 . H1111 . 1.000 no
C112 . H1121 . 1.000 no
