#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/82/1518286.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_1518286
loop_
_publ_author_name
'Stukenbroeker, Tyler S.'
'Solis-Ibarra, Diego'
'Waymouth, Robert M.'
_publ_section_title
;
 Synthesis and Topological Trapping of Cyclic Poly(alkylene phosphates)
;
_journal_issue                   23
_journal_name_full               Macromolecules
_journal_page_first              8224
_journal_paper_doi               10.1021/ma501764c
_journal_volume                  47
_journal_year                    2014
_chemical_formula_moiety         'C13 H24 Cl N2 O3 P'
_chemical_formula_sum            'C13 H24 Cl N2 O3 P'
_chemical_formula_weight         322.76
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.114(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4372(9)
_cell_length_b                   16.6637(19)
_cell_length_c                   11.7836(12)
_cell_measurement_temperature    100
_cell_volume                     1656.4(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'PHOTON 100 CMOS detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32001
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0393 after correction.
The Ratio of minimum to maximum transmission is 0.9443.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0304
_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)+(0.0377P)²+0.8396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3535
_reflns_number_total             3932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ma501764c_si_002.cif
_cod_data_source_block           final
_cod_depositor_comments          'Adding full bibliography for 1518286.cif.'
_cod_database_code               1518286
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C3(H3A,H3B,H3C), C9(H9A,
 H9B,H9C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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_calc_flag
_atom_site_refinement_flags_posn
P1 P -0.09250(3) 0.163957(17) 0.29759(2) 0.01236(8) Uani 1 d .
N2 N 0.06045(11) 0.01195(6) 0.30752(8) 0.01202(19) Uani 1 d .
N1 N 0.23390(11) 0.10836(6) 0.29967(8) 0.01346(19) Uani 1 d .
C2 C -0.09619(12) -0.02963(7) 0.29866(10) 0.0139(2) Uani 1 d .
H2 H -0.1796 0.0127 0.3048 0.017 Uiso 1 calc R
C4 C 0.07642(13) 0.09252(7) 0.29812(9) 0.0122(2) Uani 1 d .
C10 C 0.30311(14) 0.19042(7) 0.28781(11) 0.0175(2) Uani 1 d .
H10 H 0.2132 0.2275 0.2692 0.021 Uiso 1 calc R
C6 C 0.20910(13) -0.02351(7) 0.31659(9) 0.0135(2) Uani 1 d .
C5 C 0.24067(14) -0.11114(7) 0.33085(10) 0.0168(2) Uani 1 d .
H5A H 0.3480 -0.1234 0.3056 0.025 Uiso 1 calc GR
H5B H 0.1635 -0.1418 0.2853 0.025 Uiso 1 calc GR
H5C H 0.2312 -0.1257 0.4110 0.025 Uiso 1 calc GR
C1 C -0.11771(15) -0.06820(7) 0.18209(11) 0.0193(2) Uani 1 d .
H1A H -0.0967 -0.0283 0.1231 0.029 Uiso 1 calc GR
H1B H -0.2267 -0.0879 0.1732 0.029 Uiso 1 calc GR
H1C H -0.0436 -0.1131 0.1750 0.029 Uiso 1 calc GR
C7 C 0.31744(13) 0.03695(7) 0.31205(10) 0.0150(2) Uani 1 d .
C8 C 0.49393(14) 0.02900(8) 0.31628(12) 0.0233(3) Uani 1 d .
H8A H 0.5231 -0.0219 0.3527 0.035 Uiso 1 calc GR
H8B H 0.5398 0.0736 0.3600 0.035 Uiso 1 calc GR
H8C H 0.5345 0.0301 0.2389 0.035 Uiso 1 calc GR
C3 C -0.12056(15) -0.08801(8) 0.39622(11) 0.0211(3) Uani 1 d .
H3A H -0.0530 -0.1352 0.3861 0.032 Uiso 1 calc GR
H3B H -0.2319 -0.1047 0.3972 0.032 Uiso 1 calc GR
H3C H -0.0924 -0.0617 0.4682 0.032 Uiso 1 calc GR
C9 C 0.3758(2) 0.21882(9) 0.39928(13) 0.0335(3) Uani 1 d .
H9A H 0.2966 0.2154 0.4589 0.050 Uiso 1 calc GR
H9B H 0.4109 0.2746 0.3915 0.050 Uiso 1 calc GR
H9C H 0.4668 0.1848 0.4196 0.050 Uiso 1 calc GR
C11 C 0.41589(18) 0.19446(9) 0.18947(14) 0.0323(3) Uani 1 d .
H11A H 0.5154 0.1675 0.2106 0.048 Uiso 1 calc GR
H11B H 0.4374 0.2507 0.1711 0.048 Uiso 1 calc GR
H11C H 0.3678 0.1678 0.1232 0.048 Uiso 1 calc GR
O1 O -0.18316(9) 0.13872(5) 0.18175(7) 0.01501(17) Uani 1 d .
C12 C -0.12056(14) 0.16133(8) 0.07414(10) 0.0183(2) Uani 1 d .
H12A H -0.0436 0.1205 0.0490 0.022 Uiso 1 calc R
H12B H -0.0646 0.2134 0.0812 0.022 Uiso 1 calc R
C13 C -0.25381(15) 0.16824(8) -0.01142(11) 0.0204(3) Uani 1 d .
H13A H -0.2113 0.1871 -0.0845 0.024 Uiso 1 calc R
H13B H -0.3309 0.2086 0.0149 0.024 Uiso 1 calc R
O3 O -0.19568(9) 0.13987(5) 0.39140(7) 0.01651(18) Uani 1 d .
O2 O -0.02714(10) 0.24617(5) 0.28875(8) 0.01890(19) Uani 1 d .
Cl1 Cl -0.35367(4) 0.07412(2) -0.03326(3) 0.03049(10) Uani 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'
Cl Cl 0.1484 0.1585 '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
O1 P1 C4 100.82(5)
O3 P1 C4 106.68(5)
O3 P1 O1 106.67(5)
O3 P1 O2 122.00(5)
O2 P1 C4 107.84(5)
O2 P1 O1 110.73(5)
C4 N2 C2 122.91(9)
C4 N2 C6 109.70(9)
C6 N2 C2 127.19(9)
C4 N1 C10 124.20(9)
C4 N1 C7 109.27(9)
C7 N1 C10 126.52(9)
N2 C2 C1 110.38(9)
N2 C2 C3 112.07(9)
C3 C2 C1 113.29(10)
N2 C4 P1 123.94(8)
N2 C4 N1 106.94(9)
N1 C4 P1 128.89(9)
N1 C10 C9 110.92(10)
N1 C10 C11 111.37(11)
C9 C10 C11 113.57(12)
N2 C6 C5 125.71(10)
C7 C6 N2 106.74(10)
C7 C6 C5 127.55(10)
N1 C7 C8 125.63(10)
C6 C7 N1 107.35(10)
C6 C7 C8 127.00(11)
C12 O1 P1 120.32(7)
O1 C12 C13 109.30(10)
C12 C13 Cl1 111.88(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C4 1.8569(12)
P1 O1 1.6076(8)
P1 O3 1.4759(9)
P1 O2 1.4812(9)
N2 C2 1.4941(14)
N2 C4 1.3541(14)
N2 C6 1.3886(14)
N1 C4 1.3544(14)
N1 C10 1.4946(14)
N1 C7 1.3892(15)
C2 C1 1.5242(16)
C2 C3 1.5230(17)
C10 C9 1.5144(18)
C10 C11 1.5151(18)
C6 C5 1.4932(16)
C6 C7 1.3622(16)
C7 C8 1.4948(16)
O1 C12 1.4336(14)
C12 C13 1.4998(17)
C13 Cl1 1.7965(13)
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
P1 O1 C12 C13 -152.38(8)
N2 C6 C7 N1 -0.32(13)
N2 C6 C7 C8 -178.80(11)
C2 N2 C4 P1 10.79(15)
C2 N2 C4 N1 -174.39(9)
C2 N2 C6 C5 -6.48(18)
C2 N2 C6 C7 174.62(10)
C4 P1 O1 C12 -75.01(9)
C4 N2 C2 C1 102.14(12)
C4 N2 C2 C3 -130.58(11)
C4 N2 C6 C5 178.62(11)
C4 N2 C6 C7 -0.28(13)
C4 N1 C10 C9 109.06(13)
C4 N1 C10 C11 -123.40(12)
C4 N1 C7 C6 0.81(13)
C4 N1 C7 C8 179.32(11)
C10 N1 C4 P1 -7.40(16)
C10 N1 C4 N2 178.12(10)
C10 N1 C7 C6 -178.26(10)
C10 N1 C7 C8 0.26(19)
C6 N2 C2 C1 -72.14(14)
C6 N2 C2 C3 55.14(15)
C6 N2 C4 P1 -174.05(8)
C6 N2 C4 N1 0.77(12)
C5 C6 C7 N1 -179.19(11)
C5 C6 C7 C8 2.3(2)
C7 N1 C4 P1 173.51(9)
C7 N1 C4 N2 -0.97(12)
C7 N1 C10 C9 -72.01(15)
C7 N1 C10 C11 55.53(15)
O1 P1 C4 N2 -65.25(10)
O1 P1 C4 N1 121.12(10)
O1 C12 C13 Cl1 -62.40(12)
O3 P1 C4 N2 45.98(11)
O3 P1 C4 N1 -127.65(10)
O3 P1 O1 C12 173.75(8)
O2 P1 C4 N2 178.64(9)
O2 P1 C4 N1 5.01(12)
O2 P1 O1 C12 38.93(10)
