Selective adsorption of trace morpholine impurities over <i>N</i>-ethyl morpholine by tetralactam solids.
Li, Shi-Yao; Yao, Huan; Hu, Hao; Chen, Wen-Jie; Yang, Liu-Pan; Wang, Li-Li; Chemical communications (Cambridge, England) 59 (2023) 7204–7207; doi:10.1039/d3cc01164j

data_7131663
_publ_section_title
;
 Selective adsorption of trace morpholine impurities over <i>N</i>-ethyl
 morpholine by tetralactam solids.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7204
_journal_page_last               7207
_journal_paper_doi               10.1039/d3cc01164j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C48 H48 N4 O8, 4(C4 H9 N O)'
_chemical_formula_sum            'C64 H84 N8 O12'
_chemical_formula_weight         1157.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-03-04 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                84.464(3)
_cell_angle_beta                 65.455(3)
_cell_angle_gamma                74.125(3)
_cell_formula_units_Z            1
_cell_length_a                   11.4061(7)
_cell_length_b                   11.5234(8)
_cell_length_c                   13.0536(9)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      52.98
_cell_measurement_theta_min      3.24
_cell_volume                     1500.87(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27092
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.112
_diffrn_reflns_theta_max         53.112
_diffrn_reflns_theta_min         3.239
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0833 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.9344.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0062(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0865P)^2^+0.0987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3578
_reflns_number_total             5325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01164j2.cif
_cod_data_source_block           p-1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7131662--7131663.cif.'
_cod_database_code               7131663
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C34-C33
 1.58 with sigma of 0.02
 C34-N5
 1.45 with sigma of 0.02
 C35-N5
 1.48 with sigma of 0.02
 C35-C36
 1.42 with sigma of 0.02
 C33-O7
 1.39 with sigma of 0.02
 C36-O7
 1.54 with sigma of 0.02
 C31-N4
 1.45 with sigma of 0.02
 C29-N4
 1.48 with sigma of 0.02
 C29-C30
 1.42 with sigma of 0.02
 C32-O6
 1.39 with sigma of 0.02
 C30-O6
 1.54 with sigma of 0.02
 C31-C32
 1.58 with sigma of 0.02
 C35-O7
 2.48 with sigma of 0.04
 C34-O7
 2.51 with sigma of 0.04
 C34-C35
 2.4 with sigma of 0.04
 C33-C36
 2.31 with sigma of 0.04
 C31-O6
 2.51 with sigma of 0.04
 C29-O6
 2.48 with sigma of 0.04
 C31-C29
 2.4 with sigma of 0.04
 C32-C30
 2.31 with sigma of 0.04
 C34-C33 \\sim C35-C36
 with sigma of 0.04
 C34-C35 \\sim C33-C36
 with sigma of 0.02
 C31-C29 \\sim C32-C30
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O7 \\sim C36: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
O6 \\sim C30: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C31) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C36) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N5) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C36) = Uanis(C35)
Uanis(C33) = Uanis(C34)
Uanis(N5) = Uanis(O7)
Uanis(C32) = Uanis(C30)
Uanis(C29) = Uanis(C31)
Uanis(C35) = Uanis(C33)
4. Rigid body (RIGU) restrains
 O7, C36
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C34(0.5) H34A(0.5) H34B(0.5) C35(0.5) H35A(0.5) H35B(0.5) C33(0.5)
 H33A(0.5) H33B(0.5) C36(0.5) H36A(0.5) H36B(0.5) N5(0.5) H5A(0.5) O7(0.5)
 C31(0.5) H31A(0.5) H31B(0.5) C29(0.5) H29A(0.5) H29B(0.5) C32(0.5) H32A(0.5)
 H32B(0.5) C30(0.5) H30A(0.5) H30B(0.5) N4(0.5) H4A(0.5) O6(0.5)
6.a Riding coordinates:
 N5(H5A)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C21(H21A,H21B), C23(H23A,H23B), C26(H26A,H26B),
 C28(H28A,H28B), C25(H25A,H25B), C27(H27A,H27B), C34(H34A,H34B), C35(H35A,H35B),
  C33(H33A,H33B), C36(H36A,H36B), C31(H31A,H31B), C29(H29A,H29B), C32(H32A,
 H32B), C30(H30A,H30B)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C8(H8), C14(H14), C13(H13), C19(H19), C18(H18), C6(H6),
 C4(H4), N3(H3), C5(H5), N4(H4A)
6.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              53410
_shelx_hkl_checksum              7153
_olex2_submission_special_instructions 'No special instructions were received'