#------------------------------------------------------------------------------
#$Date: 2016-03-05 08:48:39 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177630 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/83/7118382.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_7118382
loop_
_publ_author_name
'Wang, Jieping'
'Siqueira, Gilberto'
'Müller, Georgina'
'Rentsch, Daniel'
'Huch, Anja'
'Tingaut, Philippe'
'Levalois-Grützmacher, Joëlle'
'Grützmacher, Hansjörg'
_publ_section_title
;
 Synthesis of new bis(acyl)phosphane oxide photoinitiators for the surface
 functionalization of cellulose nanocrystals.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2823
_journal_page_last               2826
_journal_paper_doi               10.1039/c5cc09760f
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C23 H26 N O3 P'
_chemical_formula_sum            'C23 H26 N O3 P'
_chemical_formula_weight         395.42
_chemical_melting_point          399
_chemical_name_systematic
; 
 ? 
;
_chemical_properties_physical    Light-sensitive
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-20 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                111.0320(10)
_cell_angle_beta                 94.2790(10)
_cell_angle_gamma                105.8600(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6783(2)
_cell_length_b                   11.3201(2)
_cell_length_c                   12.0032(2)
_cell_measurement_reflns_used    3962
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.49
_cell_volume                     1038.96(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14714
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular blocks'
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene/hexanes'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                3060
_reflns_number_total             3962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc09760f2.cif
_cod_data_source_block           added_by_encifer
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7118382.cif.
;
_cod_original_cell_volume        1038.96(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118382
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.23982(6) 0.08877(5) 0.17610(4) 0.01850(14) Uani 1 1 d .
O1 O 0.46823(16) 0.32511(14) 0.24470(13) 0.0354(4) Uani 1 1 d .
O2 O 0.52567(16) 0.06091(14) 0.23487(11) 0.0291(3) Uani 1 1 d .
O3 O 0.06496(14) 0.02906(13) 0.17544(11) 0.0244(3) Uani 1 1 d .
C1 C 0.3214(2) 0.27790(18) 0.23204(15) 0.0214(4) Uani 1 1 d .
C2 C 0.2047(2) 0.35363(17) 0.24110(15) 0.0204(4) Uani 1 1 d .
C3 C 0.0936(2) 0.35194(18) 0.32013(16) 0.0233(4) Uani 1 1 d .
C4 C -0.0207(2) 0.41604(19) 0.31803(18) 0.0274(4) Uani 1 1 d .
C5 C -0.0297(2) 0.48072(18) 0.23945(17) 0.0280(4) Uani 1 1 d .
C6 C 0.0866(3) 0.48596(19) 0.16621(17) 0.0290(5) Uani 1 1 d .
C7 C 0.2052(2) 0.42452(18) 0.16540(15) 0.0243(4) Uani 1 1 d .
C8 C 0.1022(4) 0.2885(3) 0.4106(2) 0.0378(6) Uani 1 1 d .
C9 C -0.1618(3) 0.5421(2) 0.2333(2) 0.0403(6) Uani 1 1 d .
H9A H -0.1365 0.5974 0.1861 0.060 Uiso 1 1 calc R
H9B H -0.1683 0.5977 0.3158 0.060 Uiso 1 1 calc R
H9C H -0.2666 0.4711 0.1940 0.060 Uiso 1 1 calc R
C10 C 0.3292(3) 0.4347(3) 0.0843(2) 0.0402(6) Uani 1 1 d .
C11 C 0.4027(2) 0.06775(17) 0.27513(15) 0.0203(4) Uani 1 1 d .
C12 C 0.3833(2) 0.08574(17) 0.40222(15) 0.0185(4) Uani 1 1 d .
C13 C 0.4944(2) 0.19605(19) 0.49939(16) 0.0232(4) Uani 1 1 d .
C14 C 0.4650(2) 0.2193(2) 0.61656(17) 0.0265(4) Uani 1 1 d .
C15 C 0.3337(2) 0.1359(2) 0.64012(16) 0.0243(4) Uani 1 1 d .
C16 C 0.2316(2) 0.0249(2) 0.54340(17) 0.0255(4) Uani 1 1 d .
C17 C 0.2534(2) -0.00327(18) 0.42392(16) 0.0215(4) Uani 1 1 d .
C18 C 0.6440(3) 0.2882(3) 0.4820(2) 0.0374(6) Uani 1 1 d .
C19 C 0.3063(3) 0.1653(3) 0.76878(19) 0.0351(5) Uani 1 1 d .
C20 C 0.1461(3) -0.1323(2) 0.32467(17) 0.0317(5) Uani 1 1 d .
H20A H 0.2085 -0.1944 0.2992 0.048 Uiso 1 1 calc R
H20B H 0.1079 -0.1147 0.2551 0.048 Uiso 1 1 calc R
H20C H 0.0521 -0.1717 0.3550 0.048 Uiso 1 1 calc R
C21 C 0.2887(3) 0.03965(19) 0.02541(16) 0.0237(4) Uani 1 1 d .
C22 C 0.2126(3) -0.1105(2) -0.05202(17) 0.0284(5) Uani 1 1 d .
C23 C 0.2676(2) -0.1945(2) -0.00088(17) 0.0297(5) Uani 1 1 d .
N1 N 0.3093(3) -0.26001(19) 0.03968(18) 0.0488(5) Uani 1 1 d .
H4 H -0.094(2) 0.4158(19) 0.3731(17) 0.022(5) Uiso 1 1 d .
H6 H 0.085(2) 0.535(2) 0.1161(19) 0.036(6) Uiso 1 1 d .
H8A H 0.036(3) 0.318(2) 0.470(2) 0.041(6) Uiso 1 1 d .
H8B H 0.060(4) 0.197(3) 0.373(3) 0.079(10) Uiso 1 1 d .
H8C H 0.215(4) 0.306(3) 0.448(3) 0.078(10) Uiso 1 1 d .
H10A H 0.310(3) 0.488(3) 0.044(2) 0.057(7) Uiso 1 1 d .
H10B H 0.449(4) 0.485(3) 0.139(3) 0.097(11) Uiso 1 1 d .
H10C H 0.327(3) 0.354(3) 0.034(2) 0.061(8) Uiso 1 1 d .
H14 H 0.536(3) 0.293(2) 0.680(2) 0.036(6) Uiso 1 1 d .
H16 H 0.140(3) -0.034(2) 0.5564(19) 0.039(6) Uiso 1 1 d .
H18A H 0.619(3) 0.324(3) 0.428(3) 0.068(8) Uiso 1 1 d .
H18B H 0.728(4) 0.242(3) 0.451(3) 0.081(10) Uiso 1 1 d .
H18C H 0.701(4) 0.358(3) 0.560(3) 0.081(9) Uiso 1 1 d .
H19A H 0.209(4) 0.096(3) 0.771(3) 0.086(10) Uiso 1 1 d .
H19B H 0.282(4) 0.243(3) 0.799(3) 0.085(10) Uiso 1 1 d .
H19C H 0.394(3) 0.164(3) 0.819(2) 0.069(8) Uiso 1 1 d .
H21A H 0.246(2) 0.086(2) -0.0143(19) 0.036(6) Uiso 1 1 d .
H21B H 0.407(3) 0.071(2) 0.0328(17) 0.029(5) Uiso 1 1 d .
H22A H 0.097(3) -0.138(2) -0.0624(19) 0.037(6) Uiso 1 1 d .
H22B H 0.239(3) -0.130(2) -0.129(2) 0.040(6) Uiso 1 1 d .
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'
P P 0.1023 0.0942 '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
O3 P1 C21 113.05(9)
O3 P1 C11 120.05(7)
C21 P1 C11 105.87(9)
O3 P1 C1 116.69(8)
C21 P1 C1 100.85(8)
C11 P1 C1 97.67(8)
O1 C1 C2 125.05(16)
O1 C1 P1 115.23(14)
C2 C1 P1 119.20(13)
C3 C2 C7 120.85(17)
C3 C2 C1 121.03(15)
C7 C2 C1 118.09(16)
C4 C3 C2 118.48(17)
C4 C3 C8 119.91(17)
C2 C3 C8 121.53(18)
C3 C4 C5 122.17(18)
C3 C4 H4 117.8(12)
C5 C4 H4 120.1(12)
C6 C5 C4 118.01(18)
C6 C5 C9 120.87(19)
C4 C5 C9 121.12(19)
C7 C6 C5 122.23(18)
C7 C6 H6 119.7(13)
C5 C6 H6 118.0(13)
C6 C7 C2 118.10(17)
C6 C7 C10 119.70(18)
C2 C7 C10 122.20(18)
C3 C8 H8A 109.1(13)
C3 C8 H8B 111.3(18)
H8A C8 H8B 107(2)
C3 C8 H8C 112.5(16)
H8A C8 H8C 113(2)
H8B C8 H8C 104(2)
C5 C9 H9A 109.5
C5 C9 H9B 109.5
H9A C9 H9B 109.5
C5 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C10 H10A 108.4(15)
C7 C10 H10B 109.7(17)
H10A C10 H10B 106(2)
C7 C10 H10C 111.2(16)
H10A C10 H10C 113(2)
H10B C10 H10C 108(2)
O2 C11 C12 125.18(16)
O2 C11 P1 115.71(13)
C12 C11 P1 118.11(13)
C17 C12 C13 120.70(15)
C17 C12 C11 120.48(15)
C13 C12 C11 118.79(15)
C14 C13 C12 118.08(17)
C14 C13 C18 119.01(18)
C12 C13 C18 122.91(17)
C15 C14 C13 122.30(18)
C15 C14 H14 119.6(12)
C13 C14 H14 118.1(13)
C16 C15 C14 118.13(17)
C16 C15 C19 121.40(18)
C14 C15 C19 120.46(19)
C15 C16 C17 122.38(17)
C15 C16 H16 120.3(13)
C17 C16 H16 117.3(13)
C16 C17 C12 118.26(17)
C16 C17 C20 119.22(16)
C12 C17 C20 122.34(16)
C13 C18 H18A 112.5(17)
C13 C18 H18B 112.8(17)
H18A C18 H18B 107(2)
C13 C18 H18C 108.9(17)
H18A C18 H18C 111(2)
H18B C18 H18C 104(2)
C15 C19 H19A 111.2(18)
C15 C19 H19B 110.2(19)
H19A C19 H19B 104(2)
C15 C19 H19C 112.0(16)
H19A C19 H19C 105(2)
H19B C19 H19C 113(3)
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C22 C21 P1 113.21(13)
C22 C21 H21A 108.0(13)
P1 C21 H21A 107.2(12)
C22 C21 H21B 112.4(12)
P1 C21 H21B 109.0(11)
H21A C21 H21B 106.7(17)
C23 C22 C21 113.77(16)
C23 C22 H22A 106.9(13)
C21 C22 H22A 111.3(13)
C23 C22 H22B 107.1(14)
C21 C22 H22B 109.9(14)
H22A C22 H22B 107.6(18)
N1 C23 C22 179.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O3 1.4810(13)
P1 C21 1.8115(18)
P1 C11 1.8981(18)
P1 C1 1.8986(19)
O1 C1 1.214(2)
O2 C11 1.214(2)
C1 C2 1.482(3)
C2 C3 1.403(2)
C2 C7 1.411(2)
C3 C4 1.383(3)
C3 C8 1.509(3)
C4 C5 1.396(3)
C4 H4 0.950(19)
C5 C6 1.390(3)
C5 C9 1.504(3)
C6 C7 1.390(3)
C6 H6 0.96(2)
C7 C10 1.513(3)
C8 H8A 0.97(2)
C8 H8B 0.92(3)
C8 H8C 0.98(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.94(3)
C10 H10B 1.07(3)
C10 H10C 0.89(3)
C11 C12 1.493(2)
C12 C17 1.402(2)
C12 C13 1.406(2)
C13 C14 1.392(2)
C13 C18 1.507(3)
C14 C15 1.386(3)
C14 H14 0.92(2)
C15 C16 1.379(3)
C15 C19 1.510(3)
C16 C17 1.392(2)
C16 H16 0.95(2)
C17 C20 1.504(3)
C18 H18A 0.92(3)
C18 H18B 1.03(3)
C18 H18C 0.96(3)
C19 H19A 1.00(3)
C19 H19B 0.92(3)
C19 H19C 0.94(3)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 C22 1.533(3)
C21 H21A 0.95(2)
C21 H21B 0.97(2)
C22 C23 1.460(3)
C22 H22A 0.95(2)
C22 H22B 0.94(2)
C23 N1 1.139(3)
