End-group functionalization of a conjugated azomethine with ureas for property tailoring
Tremblay, Marie-Hélène; Al Ahmad, Abdel; Skene, W. G.; New Journal of Chemistry 44 (2020) 18813–18822; doi:10.1039/C9NJ04722K

data_7060134
_publ_section_title
;
 End-group functionalization of a conjugated azomethine with ureas for
 property tailoring
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18813
_journal_page_last               18822
_journal_paper_doi               10.1039/C9NJ04722K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety
'2(C40 H38 N6 O10 S3), 2(C3 H6 O), 0.25(H2 O)'
_chemical_formula_sum            'C86 H88.5 N12 O22.25 S6'
_chemical_formula_weight         1838.54
_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_block_doi                 10.5517/ccdc.csd.cc20cn46
_audit_creation_date             2018-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-14 deposited with the CCDC.	2020-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.172(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7977(7)
_cell_length_b                   19.3045(9)
_cell_length_c                   29.3563(14)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    105
_cell_measurement_theta_max      60.322
_cell_measurement_theta_min      2.554
_cell_volume                     8717.2(7)
_computing_cell_refinement
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      105
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            126439
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.827
_diffrn_reflns_theta_min         2.403
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    1.378
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1313 before and 0.0779 after correction. The Ratio of minimum to maximum transmission is 0.7313. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3850
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1159
_refine_ls_number_reflns         19903
_refine_ls_number_restraints     154
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1113P)^2^+3.3100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11126
_reflns_number_total             19903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj04722k2.cif
_cod_data_source_block           sken62
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        8717.1(7)
_cod_original_formula_sum        'C86 H88.50 N12 O22.25 S6'
_cod_database_code               7060134
_shelx_shelxl_version_number     2018/3
_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, All O(H,H) groups
2. Same fragment restrains
{S11, S12, S13, O11, O12, O13, O14, O15, O16, O17, O18, O19, O110, N11, N12,
N13, N14, N15, N16, C11, C12, C13, C14, C15, C16, C17, C18, C19, C110, C111,
C112, C113, C114, C115, C116, C117, C118, C119, C120, C121, C122, C123, C124,
C125, C126, C127, C128, C129, C130, C131, C132, C133, C134, C135, C136, C137,
C138, C139, C140} sigma for 1-2: 0.02, 1-3: 0.04
as
{S21, S22, S23, O21, O22, O23, O24, O25, O26, O27, O28, O29, O210, N21, N22,
N23, N24, N25, N26, C21, C22, C23, C24, C25, C26, C27, C28, C29, C210, C211,
C212, C213, C214, C215, C216, C217, C218, C219, C220, C221, C222, C223, C224,
C225, C226, C227, C228, C229, C230, C231, C232, C233, C234, C235, C236, C237,
C238, C239, C240}
{O31, C31, C32, C33} sigma for 1-2: 0.02, 1-3: 0.04
as
{O41, C41, C42, C43}
3. Others
 Fixed Sof: O1(0.25) H1A(0.25) H1B(0.25)
4.a Free rotating group:
 O1(H1A,H1B)
4.b Secondary CH2 refined with riding coordinates:
 C118(H11A,H11B), C121(H12B,H12C), C136(H13B,H13C), C139(H13G,H13H), C218(H21A,
 H21B), C221(H22B,H22C), C236(H23B,H23C), C239(H23G,H23H)
4.c Aromatic/amide H refined with riding coordinates:
 N12(H12), N13(H13), N15(H15), N16(H16), C12(H12A), C13(H13A), C15(H15A),
 C112(H112), C113(H113), C114(H114), C115(H115), C116(H116), C123(H123),
 C130(H130), C131(H131), C132(H132), C133(H133), C134(H134), N22(H22), N23(H23),
  N25(H25), N26(H26), C22(H22A), C23(H23A), C25(H25A), C212(H212), C213(H213),
 C214(H214), C215(H215), C216(H216), C223(H223), C230(H230), C231(H231),
 C232(H232), C233(H233), C234(H234)
4.d Idealised Me refined as rotating group:
 C119(H11C,H11D,H11E), C122(H12D,H12E,H12F), C137(H13D,H13E,H13F), C140(H14A,
 H14B,H14C), C219(H21C,H21D,H21E), C222(H22D,H22E,H22F), C237(H23D,H23E,H23F),
 C240(H24A,H24B,H24C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C41(H41A,H41B,
 H41C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              86889
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'