#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558225.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_1558225
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C16.48 H14 N3.52 O2'
_chemical_formula_weight         293.34
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-07T15:23:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.548(2)
_cell_angle_beta                 106.805(2)
_cell_angle_gamma                113.770(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0515(2)
_cell_length_b                   9.7483(3)
_cell_length_c                   10.8766(3)
_cell_measurement_reflns_used    5689
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      74.26
_cell_measurement_theta_min      4.321
_cell_volume                     732.23(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0335656
_diffrn_orient_matrix_UB_12      -0.109487
_diffrn_orient_matrix_UB_13      0.0960896
_diffrn_orient_matrix_UB_21      -0.1932235
_diffrn_orient_matrix_UB_22      -0.1135621
_diffrn_orient_matrix_UB_23      -0.1046583
_diffrn_orient_matrix_UB_31      0.105402
_diffrn_orient_matrix_UB_32      -0.0789017
_diffrn_orient_matrix_UB_33      -0.0515011
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12763
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.35
_diffrn_reflns_theta_min         4.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.74
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_description       plate
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0048(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0740P)²+0.0669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0
_reflns_number_gt                2388
_reflns_number_total             2954
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           A75_BA25_250
_cod_original_cell_volume        732.24(4)
_cod_database_code               1558225
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.981
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.16648(15) 0.15534(13) 0.31181(10) 0.0590(3) Uani 1 1 d . . . . .
H1 H 0.197066 0.176747 0.392708 0.089 Uiso 1 1 calc R U . . .
O2 O 0.81979(17) 0.21785(15) 0.43492(12) 0.0692(4) Uani 1 1 d . . . . .
H2A H 0.823115 0.252961 0.507558 0.104 Uiso 1 1 calc R U . . .
N1 N 0.26116(19) 0.24786(16) -0.42113(13) 0.0579(4) Uani 1 1 d . . . . .
C1 C 0.3178(2) 0.15218(15) 0.28145(14) 0.0480(3) Uani 1 1 d . . . . .
C2 C 0.4925(2) 0.18444(16) 0.37808(14) 0.0492(3) Uani 1 1 d . . . . .
H2 H 0.507744 0.207803 0.466986 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6447(2) 0.18224(17) 0.34353(15) 0.0522(4) Uani 1 1 d . . . . .
C4 C 0.6205(3) 0.14309(18) 0.21265(16) 0.0590(4) Uani 1 1 d . . . . .
H4 H 0.72131 0.138137 0.188542 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4454(3) 0.11148(18) 0.11825(15) 0.0610(4) Uani 1 1 d . . . . .
H5 H 0.429255 0.086399 0.029373 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2935(3) 0.11561(17) 0.15042(15) 0.0567(4) Uani 1 1 d . . . . .
H6 H 0.175734 0.093986 0.084584 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3265(2) 0.3969(2) -0.37277(18) 0.0635(4) Uani 1 1 d . . . . .
H7 H 0.376775 0.467722 -0.422723 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3242(3) 0.45226(19) -0.25428(18) 0.0629(4) Uani 1 1 d . . . . .
H8 H 0.372937 0.557974 -0.223424 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2480(2) 0.34775(18) -0.18188(15) 0.0537(4) Uani 1 1 d D . . . .
C10 C 0.1832(2) 0.19393(18) -0.22923(15) 0.0558(4) Uani 1 1 d . . . . .
H10 H 0.133155 0.120759 -0.180975 0.067 Uiso 1 1 calc R U . . .
C11 C 0.1933(2) 0.14999(18) -0.34761(15) 0.0567(4) Uani 1 1 d . . . . .
H11 H 0.149918 0.045101 -0.378848 0.068 Uiso 1 1 calc R U . . .
N2A N 0.2116(8) 0.3769(5) -0.0579(4) 0.0475(10) Uani 0.665(12) 1 d D U P A 1
N3A N 0.2663(5) 0.5140(5) -0.0162(4) 0.0500(10) Uani 0.665(12) 1 d D U P A 1
C12A C 0.2322(10) 0.5541(6) 0.1008(5) 0.0426(9) Uani 0.665(12) 1 d . U P A 1
C13A C 0.2846(12) 0.7061(6) 0.1459(6) 0.0525(10) Uani 0.665(12) 1 d . U P A 1
H13A H 0.341476 0.782021 0.101894 0.063 Uiso 0.665(12) 1 calc R U P A 1
C14A C 0.2505(14) 0.7432(6) 0.2584(8) 0.0577(15) Uani 0.665(12) 1 d . U P A 1
H14A H 0.287159 0.846992 0.289103 0.069 Uiso 0.665(12) 1 calc R U P A 1
N4A N 0.1716(13) 0.6454(8) 0.3248(7) 0.0532(12) Uani 0.665(12) 1 d . U P A 1
C15A C 0.1206(11) 0.4999(8) 0.2789(6) 0.0523(10) Uani 0.665(12) 1 d . U P A 1
H15A H 0.06213 0.42713 0.324742 0.063 Uiso 0.665(12) 1 calc R U P A 1
C16A C 0.1470(8) 0.4476(5) 0.1687(6) 0.0482(11) Uani 0.665(12) 1 d . U P A 1
H16A H 0.108169 0.342798 0.14066 0.058 Uiso 0.665(12) 1 calc R U P A 1
C12B C 0.2090(18) 0.5169(12) 0.1206(10) 0.046(2) Uani 0.335(12) 1 d DG U P A 2
C13B C 0.283(2) 0.6755(12) 0.1464(12) 0.057(2) Uani 0.335(12) 1 d G U P A 2
H13B H 0.341473 0.732361 0.09133 0.068 Uiso 0.335(12) 1 calc R U P A 2
C14B C 0.269(3) 0.7502(11) 0.2537(15) 0.058(3) Uani 0.335(12) 1 d G U P A 2
H14B H 0.319113 0.857416 0.271141 0.069 Uiso 0.335(12) 1 calc R U P A 2
N4B N 0.182(3) 0.6661(16) 0.3351(13) 0.060(3) Uani 0.335(12) 1 d G U P A 2
C15B C 0.109(2) 0.5075(15) 0.3093(11) 0.055(2) Uani 0.335(12) 1 d G U P A 2
H15B H 0.049834 0.450721 0.364374 0.066 Uiso 0.335(12) 1 calc R U P A 2
C16B C 0.1220(17) 0.4329(10) 0.2020(11) 0.053(2) Uani 0.335(12) 1 d G U P A 2
H16B H 0.072192 0.325663 0.184564 0.064 Uiso 0.335(12) 1 calc R U P A 2
C17 C 0.231(2) 0.460(3) 0.0190(11) 0.052(3) Uani 0.239(16) 1 d D U P A 2
C18 C 0.257(2) 0.417(3) -0.0746(14) 0.054(3) Uani 0.239(16) 1 d D U P A 2
N2B N 0.287(4) 0.479(4) -0.066(3) 0.061(4) Uani 0.097(8) 1 d D U P A 3
N3B N 0.185(3) 0.397(3) -0.007(3) 0.054(5) Uani 0.097(8) 1 d D U P A 3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 -4 -4 0.116
-2 4 4 0.0741
0 5 -5 0.001
3 3 -3 0.045
4 -1 1 0.0687
0 -5 5 0.0227
-4 1 -1 0.0879
0 -4 -4 0.1248
3 -5 -4 0.107
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 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.00(14) . . ?
O1 C1 C6 118.14(14) . . ?
O1 C1 C2 121.64(13) . . ?
C6 C1 C2 120.22(14) . . ?
C1 C2 C3 120.12(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.13(14) . . ?
O2 C3 C2 121.88(13) . . ?
C4 C3 C2 119.99(15) . . ?
C5 C4 C3 118.84(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 122.04(14) . . ?
C6 C5 H5 119 . . ?
C4 C5 H5 119 . . ?
C5 C6 C1 118.76(15) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.72(16) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.97(15) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C10 130.8(12) . . ?
C18 C9 C8 110.2(12) . . ?
C10 C9 C8 119.02(15) . . ?
C10 C9 N2A 112.6(2) . . ?
C8 C9 N2A 128.3(2) . . ?
C10 C9 N2B 147.9(8) . . ?
C8 C9 N2B 93.0(8) . . ?
C11 C10 C9 118.74(15) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.52(15) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N3A N2A C9 112.9(6) . . ?
N2A N3A C12A 117.2(6) . . ?
C13A C12A C16A 118.5(3) . . ?
C13A C12A N3A 118.2(4) . . ?
C16A C12A N3A 123.3(4) . . ?
C12A C13A C14A 117.7(3) . . ?
C12A C13A H13A 121.2 . . ?
C14A C13A H13A 121.2 . . ?
N4A C14A C13A 125.1(3) . . ?
N4A C14A H14A 117.4 . . ?
C13A C14A H14A 117.4 . . ?
C14A N4A C15A 116.1(3) . . ?
N4A C15A C16A 124.6(4) . . ?
N4A C15A H15A 117.7 . . ?
C16A C15A H15A 117.7 . . ?
C15A C16A C12A 117.9(3) . . ?
C15A C16A H16A 121.1 . . ?
C12A C16A H16A 121.1 . . ?
C17 C12B C13B 114.7(11) . . ?
C17 C12B C16B 125.3(11) . . ?
C13B C12B C16B 120 . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C14B N4B C15B 120 . . ?
N4B C15B C16B 120 . . ?
N4B C15B H15B 120 . . ?
C16B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 176(3) . . ?
C17 C18 C9 167(3) . . ?
N3B N2B C9 99(3) . . ?
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 1.3620(18) . ?
O1 H1 0.83 . ?
O2 C3 1.3593(19) . ?
O2 H2A 0.83 . ?
N1 C11 1.332(2) . ?
N1 C7 1.340(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.94 . ?
C3 C4 1.386(2) . ?
C4 C5 1.382(2) . ?
C4 H4 0.94 . ?
C5 C6 1.380(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.374(3) . ?
C7 H7 0.94 . ?
C8 C9 1.382(3) . ?
C8 H8 0.94 . ?
C9 C18 1.281(13) . ?
C9 C10 1.380(2) . ?
C9 N2A 1.495(6) . ?
C9 N2B 1.61(4) . ?
C10 C11 1.367(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.233(6) . ?
N3A C12A 1.441(6) . ?
C12A C13A 1.379(5) . ?
C12A C16A 1.381(4) . ?
C13A C14A 1.386(5) . ?
C13A H13A 0.94 . ?
C14A N4A 1.302(5) . ?
C14A H14A 0.94 . ?
N4A C15A 1.324(5) . ?
C15A C16A 1.379(5) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.296(12) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C13B C14B 1.39 . ?
C13B H13B 0.94 . ?
C14B N4B 1.39 . ?
C14B H14B 0.94 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.94 . ?
C16B H16B 0.94 . ?
C17 C18 1.181(16) . ?
N2B N3B 1.25(2) . ?
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
O1 H1 N1 0.83 1.94 2.7700(17) 173 1_556 yes
O2 H2A N4A 0.83 2 2.829(5) 174.4 2_666 yes
O2 H2A N4B 0.83 1.86 2.69(6) 176.5 2_666 yes
