#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:41:23 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287295 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/99/1569983.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_1569983
loop_
_publ_author_name
'Contreras-Montoya, Rafael'
'Smith, James P.'
'Boothroyd, Stephen C.'
'Aguilar, Juan A.'
'Mirzamani, Marzieh'
'Screen, Martin A.'
'Yufit, Dmitry S.'
'Robertson, Mark'
'He, Lilin'
'Qian, Shuo'
'Kumari, Harshita'
'Steed, Jonathan W.'
_publ_section_title
;
 Pathway complexity in fibre assembly: from liquid crystals to
 hyper-helical gelmorphs.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              11389
_journal_page_last               11401
_journal_paper_doi               10.1039/d3sc03841f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C21 H26 N6 O4, 2(C2 H3 N)'
_chemical_formula_sum            'C25 H32 N8 O4'
_chemical_formula_weight         508.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-28 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.235(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   38.366(10)
_cell_length_b                   4.5756(11)
_cell_length_c                   15.248(4)
_cell_measurement_reflns_used    7266
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.66
_cell_volume                     2642.1(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'φ and ω rotation with 0.1 degree frames'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21296
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.085
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1411 before and 0.1018 after correction. 
The Ratio of minimum to maximum transmission is 0.7337. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.003
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0679
_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/[σ²(Fo²)+(0.1230P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1924
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2855
_reflns_number_total             3862
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03841f2.cif
_cod_data_source_block           1RR_AcNA_19srv317
_cod_depositor_comments
'Adding full bibliography for 1569983--1569987.cif.'
_cod_original_cell_volume        2642.1(11)
_cod_database_code               1569983
_shelx_shelxl_version_number     2017/1
_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.
;
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.974
_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. Restrained distances
 N1-H1 \\sim N2-H2 \\sim N3-H3
 with sigma of 0.005
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C2S(H2SA,H2SB,H2SC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.11208(3) 0.7839(2) 0.39265(7) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.02192(3) 0.2639(2) 0.35933(8) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.13755(3) 0.3551(2) 0.44456(8) 0.0233(3) Uani 1 1 d D . . . .
N2 N 0.09012(3) 0.3522(3) 0.33262(9) 0.0276(3) Uani 1 1 d D . . . .
N3 N 0.06084(3) 0.4942(3) 0.28630(9) 0.0242(3) Uani 1 1 d D . . . .
C1 C 0.11323(3) 0.5142(3) 0.39142(9) 0.0208(3) Uani 1 1 d . . . . .
C2 C 0.02834(3) 0.4416(3) 0.30379(9) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.000000 0.6274(4) 0.250000 0.0229(4) Uani 1 2 d S T P . .
H3A H -0.010900 0.754613 0.290591 0.027 Uiso 0.5 1 calc R . . . .
H3B H 0.010900 0.754613 0.209409 0.027 Uiso 0.5 1 calc R . . . .
C4 C 0.16733(4) 0.4934(3) 0.50195(9) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.158616 0.680401 0.524617 0.025 Uiso 1 1 calc R . . . .
C5 C 0.19650(4) 0.5691(4) 0.44897(10) 0.0284(3) Uani 1 1 d . . . . .
H5A H 0.205116 0.389876 0.424517 0.043 Uiso 1 1 calc GR . . . .
H5B H 0.215972 0.664666 0.487969 0.043 Uiso 1 1 calc GR . . . .
H5C H 0.187196 0.701523 0.400285 0.043 Uiso 1 1 calc GR . . . .
C6 C 0.17842(4) 0.2943(3) 0.58137(9) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.21212(4) 0.1786(3) 0.60194(10) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.229466 0.226995 0.566362 0.031 Uiso 1 1 calc R . . . .
C8 C 0.22076(4) -0.0076(4) 0.67419(11) 0.0325(4) Uani 1 1 d . . . . .
H8 H 0.243969 -0.085247 0.687782 0.039 Uiso 1 1 calc R . . . .
C9 C 0.19595(5) -0.0796(4) 0.72584(11) 0.0367(4) Uani 1 1 d . . . . .
H9 H 0.201833 -0.209308 0.774627 0.044 Uiso 1 1 calc R . . . .
C10 C 0.16218(5) 0.0372(4) 0.70677(12) 0.0380(4) Uani 1 1 d . . . . .
H10 H 0.144974 -0.010873 0.742814 0.046 Uiso 1 1 calc R . . . .
C11 C 0.15365(4) 0.2237(4) 0.63516(11) 0.0298(4) Uani 1 1 d . . . . .
H11 H 0.130583 0.304560 0.622609 0.036 Uiso 1 1 calc R . . . .
H1 H 0.1368(5) 0.165(3) 0.4371(13) 0.039(5) Uiso 1 1 d D . . . .
H2 H 0.0886(5) 0.162(3) 0.3385(14) 0.044(6) Uiso 1 1 d D . . . .
H3 H 0.0650(5) 0.609(4) 0.2429(10) 0.030(5) Uiso 1 1 d D . . . .
N1S N 0.06730(4) -0.0952(4) 0.14127(12) 0.0472(4) Uani 1 1 d . . . . .
C1S C 0.05692(4) 0.0581(4) 0.08467(11) 0.0308(4) Uani 1 1 d . . . . .
C2S C 0.04318(5) 0.2493(4) 0.01175(12) 0.0387(4) Uani 1 1 d . . . . .
H2SA H 0.041073 0.140927 -0.044296 0.058 Uiso 1 1 calc GR . . . .
H2SB H 0.059277 0.414792 0.010145 0.058 Uiso 1 1 calc GR . . . .
H2SC H 0.019884 0.321652 0.019983 0.058 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 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 '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
C1 N1 C4 121.59(11) . . ?
C1 N1 H1 117.0(13) . . ?
C4 N1 H1 120.7(13) . . ?
N3 N2 H2 117.0(14) . . ?
C1 N2 N3 117.69(12) . . ?
C1 N2 H2 121.0(14) . . ?
N2 N3 H3 115.8(12) . . ?
C2 N3 N2 121.21(13) . . ?
C2 N3 H3 122.9(12) . . ?
O1 C1 N1 123.63(12) . . ?
O1 C1 N2 121.90(12) . . ?
N1 C1 N2 114.43(12) . . ?
O2 C2 N3 123.61(13) . . ?
O2 C2 C3 122.66(12) . . ?
N3 C2 C3 113.71(12) . . ?
C2 C3 C2 111.67(15) 2 . ?
C2 C3 H3A 109.3 2 . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 2 . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 H4 107.7 . . ?
N1 C4 C5 110.50(12) . . ?
N1 C4 C6 107.96(10) . . ?
C5 C4 H4 107.7 . . ?
C6 C4 H4 107.7 . . ?
C6 C4 C5 115.05(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 122.75(14) . . ?
C7 C6 C11 118.64(14) . . ?
C11 C6 C4 118.61(13) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.60(15) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.24(15) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.89(16) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.82(17) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.80(15) . . ?
C10 C11 H11 119.6 . . ?
N1S C1S C2S 178.9(2) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
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
O1 C1 1.2351(16) . ?
O2 C2 1.2268(19) . ?
N1 C1 1.3469(16) . ?
N1 C4 1.4664(16) . ?
N1 H1 0.877(13) . ?
N2 N3 1.3887(15) . ?
N2 C1 1.3728(17) . ?
N2 H2 0.878(13) . ?
N3 C2 1.338(2) . ?
N3 H3 0.880(13) . ?
C2 C3 1.5138(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 1.0000 . ?
C4 C5 1.522(2) . ?
C4 C6 1.5207(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.385(2) . ?
C6 C11 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?
N1S C1S 1.133(2) . ?
C1S C2S 1.446(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.877(13) 2.048(15) 2.8574(16) 152.9(17) 1_545 yes
N2 H2 O1 0.878(13) 2.061(15) 2.8392(16) 147.3(19) 1_545 yes
N3 H3 N1S 0.880(13) 2.069(14) 2.943(2) 171.6(17) 1_565 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 N3 169.36(13) . . . . ?
N2 N3 C2 O2 -1.6(2) . . . . ?
N3 N2 C1 O1 -12.7(2) . . . . ?
C1 N2 N3 C2 -109.36(16) . . . . ?
C2 N3 N2 C1 -109.36(16) . . . . ?
C2 C3 C2 O2 -58.94(12) 2 . . . ?
C2 C3 C2 N3 122.39(13) 2 . . . ?
C3 C2 N3 N2 177.08(12) . . . . ?
C4 N1 C1 O1 -7.0(2) . . . . ?
C4 N1 C1 N2 170.92(13) . . . . ?
C5 C4 N1 C1 -80.74(17) . . . . ?
C5 C4 C6 C7 -2.85(19) . . . . ?
C5 C4 C6 C11 177.61(13) . . . . ?
C6 C4 N1 C1 152.65(13) . . . . ?
C7 C6 C4 N1 121.06(15) . . . . ?
C7 C6 C4 C5 -2.85(19) . . . . ?
C11 C6 C4 N1 -58.48(17) . . . . ?
