#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:25:01 +0300 (Wed, 05 May 2021) $
#$Revision: 264893 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/10/1561099.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_1561099
loop_
_publ_author_name
'Jones, Zachary R.'
'Livshits, Maksim Y.'
'White, Frankie D.'
'Dalodière, Elodie'
'Ferrier, Maryline G.'
'Lilley, Laura M.'
'Knope, Karah E.'
'Kozimor, Stosh A.'
'Mocko, Veronika'
'Scott, Brian L.'
'Stein, Benjamin W.'
'Wacker, Jennifer N.'
'Woen, David H.'
_publ_section_title
;
 Advancing understanding of actinide(iii) (Ac, Am, Cm) aqueous
 complexation chemistry
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              5638
_journal_page_last               5654
_journal_paper_doi               10.1039/D1SC00233C
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety
'Cm H2O 3(C2 O2 H3) 2(C2 O2 H3) 2(N H4) + [solvent]'
_chemical_formula_sum            'C10 H25 Cm N2 O11'
_chemical_formula_weight         593.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-14 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7801(3)
_cell_length_b                   15.0056(7)
_cell_length_c                   20.4890(10)
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.42
_cell_volume                     2067.92(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         2.715
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.989
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.6662.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            lemonade
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.823
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0340P)²+2.2266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4603
_reflns_number_total             5093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc00233c2.cif
_cod_data_source_block           cmoac_1
_cod_depositor_comments
'Adding full bibliography for 1561098--1561100.cif.'
_cod_original_formula_sum        'Cm O11 N2 C10 H25'
_cod_database_code               1561099
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 N1(H1D,H1E,H1F), N1(H1G), N2(H2A,H2B,H2C), N2(H2D)
2.b Free rotating group:
 O11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C5(H5A,H5B,H5C), C9(H9A,
 H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cm1 Cm 0.53075(2) 0.59590(2) 0.28222(2) 0.02372(5) Uani 1 1 d . . . . .
O4 O 0.4049(4) 0.46790(19) 0.34824(15) 0.0379(7) Uani 1 1 d . . . . .
O10 O 0.4176(6) 0.7919(2) 0.11635(16) 0.0527(9) Uani 1 1 d . . . . .
O1 O 0.4996(5) 0.7526(2) 0.32807(15) 0.0426(7) Uani 1 1 d . . . . .
O6 O -0.1298(4) 0.6432(2) 0.29699(15) 0.0397(7) Uani 1 1 d . . . . .
O3 O 0.7259(4) 0.4759(2) 0.35073(16) 0.0421(7) Uani 1 1 d . . . . .
N1 N 0.4584(5) 0.8934(2) 0.2351(2) 0.0376(8) Uani 1 1 d . . . . .
H1D H 0.452290 0.951229 0.225350 0.045 Uiso 1 1 d R . . . .
H1E H 0.360690 0.879459 0.258480 0.045 Uiso 1 1 d R . . . .
H1F H 0.575030 0.881289 0.258480 0.045 Uiso 1 1 d R . . . .
H1G H 0.445350 0.860989 0.197270 0.045 Uiso 1 1 d R . . . .
O5 O 0.1810(4) 0.6192(2) 0.28563(18) 0.0457(8) Uani 1 1 d . . . . .
O8 O 0.6915(5) 0.4940(2) 0.20560(17) 0.0506(8) Uani 1 1 d . . . . .
O2 O 0.5387(5) 0.6474(2) 0.40152(15) 0.0451(7) Uani 1 1 d . . . . .
O9 O 0.4961(5) 0.6856(2) 0.18760(15) 0.0452(8) Uani 1 1 d . . . . .
O7 O 0.3688(5) 0.4826(2) 0.20167(18) 0.0538(9) Uani 1 1 d . . . . .
N2 N -0.1405(5) 0.6167(2) 0.50234(16) 0.0368(8) Uani 1 1 d . . . . .
H2A H -0.246280 0.643811 0.480969 0.044 Uiso 1 1 d R . . . .
H2B H -0.180140 0.573571 0.527479 0.044 Uiso 1 1 d R . . . .
H2C H -0.068040 0.656131 0.527479 0.044 Uiso 1 1 d R . . . .
H2D H -0.065820 0.592921 0.472779 0.044 Uiso 1 1 d R . . . .
C4 C 0.5753(6) 0.4433(3) 0.37142(19) 0.0288(7) Uani 1 1 d . . . . .
O11 O 0.0884(5) 0.5422(3) 0.4118(2) 0.0679(11) Uani 1 1 d . . . . .
H11A H 0.187962 0.561021 0.394413 0.102 Uiso 1 1 d G . . . .
H11B H 0.138758 0.517320 0.447314 0.102 Uiso 1 1 d G . . . .
C6 C 0.0211(5) 0.6588(3) 0.27036(19) 0.0303(8) Uani 1 1 d . . . . .
C10 C 0.4679(6) 0.7140(3) 0.1298(2) 0.0369(9) Uani 1 1 d . . . . .
C2 C 0.5128(6) 0.7288(3) 0.3863(2) 0.0365(9) Uani 1 1 d . . . . .
C8 C 0.5291(7) 0.4589(3) 0.1820(2) 0.0454(11) Uani 1 1 d . . . . .
C3 C 0.5999(8) 0.3739(4) 0.4244(2) 0.0486(11) Uani 1 1 d . . . . .
H3A H 0.731625 0.349389 0.427607 0.073 Uiso 1 1 calc GR . . . .
H3B H 0.504203 0.327257 0.413903 0.073 Uiso 1 1 calc GR . . . .
H3C H 0.579798 0.400491 0.465653 0.073 Uiso 1 1 calc GR . . . .
C1 C 0.4926(10) 0.7942(4) 0.4395(3) 0.0705(17) Uani 1 1 d . . . . .
H1A H 0.462545 0.851913 0.420544 0.106 Uiso 1 1 calc GR . . . .
H1B H 0.614956 0.797103 0.468609 0.106 Uiso 1 1 calc GR . . . .
H1C H 0.387156 0.775909 0.463696 0.106 Uiso 1 1 calc GR . . . .
C7 C 0.5290(12) 0.3897(5) 0.1291(4) 0.092(3) Uani 1 1 d . . . . .
H7A H 0.516120 0.418257 0.086818 0.138 Uiso 1 1 calc GR . . . .
H7B H 0.419480 0.349625 0.130968 0.138 Uiso 1 1 calc GR . . . .
H7C H 0.651480 0.356840 0.135551 0.138 Uiso 1 1 calc GR . . . .
C5 C 0.0090(8) 0.7311(4) 0.2204(3) 0.0612(16) Uani 1 1 d . . . . .
H5A H -0.120050 0.730485 0.194984 0.092 Uiso 1 1 calc GR . . . .
H5B H 0.108976 0.721930 0.191793 0.092 Uiso 1 1 calc GR . . . .
H5C H 0.030258 0.787624 0.242098 0.092 Uiso 1 1 calc GR . . . .
C9 C 0.5006(14) 0.6530(5) 0.0754(3) 0.097(3) Uani 1 1 d . . . . .
H9A H 0.382011 0.619078 0.062699 0.146 Uiso 1 1 calc GR . . . .
H9B H 0.608422 0.613353 0.089816 0.146 Uiso 1 1 calc GR . . . .
H9C H 0.532585 0.687148 0.038555 0.146 Uiso 1 1 calc GR . . . .
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'
Cm Cm -7.3248 4.8980 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cm1 O2 71.91(10) . . ?
O4 Cm1 C4 25.23(10) . . ?
O4 Cm1 C2 94.53(11) . . ?
O4 Cm1 C8 82.57(13) . . ?
O1 Cm1 O4 116.68(10) . . ?
O1 Cm1 O2 50.38(9) . . ?
O1 Cm1 C4 119.94(10) . . ?
O1 Cm1 C2 24.84(10) . . ?
O1 Cm1 C8 156.87(12) . . ?
O6 Cm1 O4 122.43(10) 1_655 . ?
O6 Cm1 O1 78.62(11) 1_655 . ?
O6 Cm1 O3 73.46(10) 1_655 . ?
O6 Cm1 O5 152.80(12) 1_655 . ?
O6 Cm1 O8 77.02(11) 1_655 . ?
O6 Cm1 O2 83.42(11) 1_655 . ?
O6 Cm1 O7 127.99(11) 1_655 . ?
O6 Cm1 C4 97.56(11) 1_655 . ?
O6 Cm1 C2 80.43(11) 1_655 . ?
O6 Cm1 C8 102.56(13) 1_655 . ?
O3 Cm1 O4 50.41(9) . . ?
O3 Cm1 O1 120.65(10) . . ?
O3 Cm1 O2 74.94(10) . . ?
O3 Cm1 C4 25.33(10) . . ?
O3 Cm1 C2 98.42(11) . . ?
O3 Cm1 C8 81.08(12) . . ?
O5 Cm1 O4 72.42(10) . . ?
O5 Cm1 O1 74.20(12) . . ?
O5 Cm1 O3 122.12(10) . . ?
O5 Cm1 O8 127.44(12) . . ?
O5 Cm1 O2 80.24(12) . . ?
O5 Cm1 O7 76.57(12) . . ?
O5 Cm1 C4 96.91(11) . . ?
O5 Cm1 C2 75.44(12) . . ?
O5 Cm1 C8 101.97(14) . . ?
O8 Cm1 O4 94.18(11) . . ?
O8 Cm1 O1 147.82(11) . . ?
O8 Cm1 O3 71.40(11) . . ?
O8 Cm1 O2 144.64(10) . . ?
O8 Cm1 C4 84.03(11) . . ?
O8 Cm1 C2 157.09(11) . . ?
O8 Cm1 C8 25.66(12) . . ?
O2 Cm1 C4 69.57(10) . . ?
O2 Cm1 C2 25.55(10) . . ?
O2 Cm1 C8 152.53(12) . . ?
O9 Cm1 O4 149.58(11) . . ?
O9 Cm1 O1 76.77(11) . . ?
O9 Cm1 O6 85.91(11) . 1_655 ?
O9 Cm1 O3 148.31(11) . . ?
O9 Cm1 O5 86.81(11) . . ?
O9 Cm1 O8 80.82(12) . . ?
O9 Cm1 O2 127.15(11) . . ?
O9 Cm1 O7 81.73(12) . . ?
O9 Cm1 C4 163.28(12) . . ?
O9 Cm1 C2 101.61(12) . . ?
O9 Cm1 C8 80.26(13) . . ?
O7 Cm1 O4 72.13(11) . . ?
O7 Cm1 O1 144.38(11) . . ?
O7 Cm1 O3 92.13(13) . . ?
O7 Cm1 O8 51.22(11) . . ?
O7 Cm1 O2 141.62(11) . . ?
O7 Cm1 C4 83.28(12) . . ?
O7 Cm1 C2 151.56(12) . . ?
O7 Cm1 C8 25.56(12) . . ?
C4 Cm1 C2 95.10(11) . . ?
C8 Cm1 C4 83.02(13) . . ?
C8 Cm1 C2 176.63(13) . . ?
C4 O4 Cm1 94.0(2) . . ?
C2 O1 Cm1 95.1(3) . . ?
C6 O6 Cm1 146.5(3) . 1_455 ?
C4 O3 Cm1 94.2(2) . . ?
C6 O5 Cm1 153.5(3) . . ?
C8 O8 Cm1 93.8(3) . . ?
C2 O2 Cm1 94.0(2) . . ?
C10 O9 Cm1 164.8(3) . . ?
C8 O7 Cm1 94.5(3) . . ?
O4 C4 Cm1 60.81(19) . . ?
O4 C4 O3 120.7(3) . . ?
O4 C4 C3 119.7(4) . . ?
O3 C4 Cm1 60.4(2) . . ?
O3 C4 C3 119.7(4) . . ?
C3 C4 Cm1 172.4(3) . . ?
O6 C6 O5 122.8(4) . . ?
O6 C6 C5 117.6(4) . . ?
O5 C6 C5 119.6(4) . . ?
O10 C10 O9 122.6(4) . . ?
O10 C10 C9 118.6(4) . . ?
O9 C10 C9 118.8(5) . . ?
O1 C2 Cm1 60.0(2) . . ?
O1 C2 O2 120.5(4) . . ?
O1 C2 C1 120.9(4) . . ?
O2 C2 Cm1 60.5(2) . . ?
O2 C2 C1 118.6(4) . . ?
C1 C2 Cm1 176.8(4) . . ?
O8 C8 Cm1 60.5(2) . . ?
O8 C8 C7 119.1(5) . . ?
O7 C8 Cm1 60.0(2) . . ?
O7 C8 O8 120.5(4) . . ?
O7 C8 C7 120.4(5) . . ?
C7 C8 Cm1 178.7(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cm1 O4 2.557(3) . ?
Cm1 O1 2.551(3) . ?
Cm1 O6 2.391(3) 1_655 ?
Cm1 O3 2.548(3) . ?
Cm1 O5 2.407(3) . ?
Cm1 O8 2.534(3) . ?
Cm1 O2 2.558(3) . ?
Cm1 O9 2.348(3) . ?
Cm1 O7 2.523(3) . ?
Cm1 C4 2.922(4) . ?
Cm1 C2 2.933(4) . ?
Cm1 C8 2.904(5) . ?
O4 C4 1.249(5) . ?
O10 C10 1.238(5) . ?
O1 C2 1.237(5) . ?
O6 C6 1.241(4) . ?
O3 C4 1.254(5) . ?
O5 C6 1.241(4) . ?
O8 C8 1.260(6) . ?
O2 C2 1.268(5) . ?
O9 C10 1.250(5) . ?
O7 C8 1.257(6) . ?
C4 C3 1.498(6) . ?
C6 C5 1.487(6) . ?
C10 C9 1.480(8) . ?
C2 C1 1.487(6) . ?
C8 C7 1.502(8) . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.499 0.000 0.500 115.9 29.6 ?
2 0.083 0.500 0.000 115.9 29.6 ?
