#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558249.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_1558249
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            'C16.46 H14.46 N3.54 O2'
_chemical_formula_weight         293.85
_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             2020-03-12T16:25:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.9195(13)
_cell_angle_beta                 106.4603(14)
_cell_angle_gamma                113.7186(15)
_cell_formula_units_Z            2
_cell_length_a                   8.02672(12)
_cell_length_b                   9.79494(16)
_cell_length_c                   10.86753(18)
_cell_measurement_reflns_used    12760
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      75.488
_cell_measurement_theta_min      4.302
_cell_volume                     733.83(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      270(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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      -0.0287982
_diffrn_orient_matrix_UB_12      -0.1656182
_diffrn_orient_matrix_UB_13      -0.0028696
_diffrn_orient_matrix_UB_21      -0.0997322
_diffrn_orient_matrix_UB_22      -0.0388472
_diffrn_orient_matrix_UB_23      -0.1499918
_diffrn_orient_matrix_UB_31      0.1973026
_diffrn_orient_matrix_UB_32      0.0436369
_diffrn_orient_matrix_UB_33      -0.018127
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27725
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.344
_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    0.738
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
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 yellow'
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0047(10)
_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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0667P)²+0.0966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0
_reflns_number_gt                2606
_reflns_number_total             3022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A75_BE25_270
_cod_database_code               1558249
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.96
_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 0.16592(14) 0.15854(12) 0.31174(9) 0.0586(3) Uani 1 1 d . . . . .
H1 H 0.197343 0.184141 0.391441 0.088 Uiso 1 1 calc R U . . .
O2 O 0.82104(15) 0.22302(14) 0.43379(10) 0.0683(3) Uani 1 1 d . . . . .
H2A H 0.825295 0.260296 0.505162 0.102 Uiso 1 1 calc R U . . .
N1 N 0.26020(17) 0.24881(14) 0.57919(11) 0.0569(3) Uani 1 1 d . . . . .
N2A N 0.2134(19) 0.3778(8) 0.9427(9) 0.0497(9) Uani 0.677(3) 1 d D U P A 1
N3A N 0.2634(10) 0.5148(7) 0.9803(4) 0.0470(8) Uani 0.677(3) 1 d D U P A 1
C17 C 0.215(7) 0.376(3) 0.940(3) 0.051(3) Uani 0.230(3) 1 d D U P A 2
H17 H 0.151413 0.295151 0.97475 0.062 Uiso 0.230(3) 1 calc R U P A 2
C18 C 0.276(4) 0.516(3) 1.0031(14) 0.052(2) Uani 0.230(3) 1 d D U P A 2
H18 H 0.357397 0.595897 0.974693 0.062 Uiso 0.230(3) 1 calc DR U P A 2
N2B N 0.2798(19) 0.4720(18) 0.9289(13) 0.053(2) Uani 0.093(2) 1 d D U P A 3
N3B N 0.1884(18) 0.4020(16) 0.9976(14) 0.053(2) Uani 0.093(2) 1 d D U P A 3
N4 N 0.17673(16) 0.64993(13) 1.32807(10) 0.0547(3) Uani 1 1 d . . . . .
C1 C 0.31740(19) 0.15436(13) 0.28172(12) 0.0475(3) Uani 1 1 d . . . . .
C2 C 0.49272(19) 0.18892(14) 0.37744(12) 0.0483(3) Uani 1 1 d . . . . .
H2 H 0.508427 0.214411 0.465361 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6455(2) 0.18578(14) 0.34306(12) 0.0510(3) Uani 1 1 d . . . . .
C4 C 0.6205(2) 0.14389(16) 0.21174(14) 0.0577(3) Uani 1 1 d . . . . .
H4 H 0.720775 0.139098 0.187756 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4449(2) 0.10963(16) 0.11783(13) 0.0593(4) Uani 1 1 d . . . . .
H5 H 0.428382 0.082487 0.029985 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2925(2) 0.11440(15) 0.15025(13) 0.0559(3) Uani 1 1 d . . . . .
H6 H 0.17532 0.09128 0.085258 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3232(2) 0.39634(17) 0.62868(14) 0.0598(4) Uani 1 1 d . . . . .
H7 H 0.372437 0.467005 0.579901 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3194(2) 0.44958(16) 0.74816(14) 0.0576(3) Uani 1 1 d . . . . .
H8 H 0.366412 0.553449 0.779654 0.069 Uiso 1 1 calc DR U . . .
C9 C 0.24358(19) 0.34421(16) 0.82000(12) 0.0505(3) Uani 1 1 d D . . . .
C10 C 0.1817(2) 0.19196(16) 0.77093(13) 0.0565(3) Uani 1 1 d . . . . .
H10 H 0.132995 0.118851 0.817971 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1930(2) 0.14992(16) 0.65158(14) 0.0577(3) Uani 1 1 d . . . . .
H11 H 0.151498 0.046973 0.619601 0.069 Uiso 1 1 calc R U . . .
C12 C 0.23101(19) 0.55121(16) 1.10348(12) 0.0519(3) Uani 1 1 d D . . . .
C13 C 0.2861(2) 0.70233(17) 1.14691(14) 0.0600(4) Uani 1 1 d . . . . .
H13 H 0.342344 0.774285 1.101292 0.072 Uiso 1 1 calc R U . . .
C14 C 0.2575(2) 0.74625(16) 1.25821(14) 0.0606(4) Uani 1 1 d . . . . .
H14 H 0.296865 0.849565 1.286869 0.073 Uiso 1 1 calc R U . . .
C15 C 0.1213(2) 0.50203(16) 1.28554(13) 0.0551(3) Uani 1 1 d . . . . .
H15 H 0.0639 0.432813 1.332708 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1458(2) 0.44710(16) 1.17407(14) 0.0571(3) Uani 1 1 d . . . . .
H16 H 0.106224 0.343426 1.147192 0.068 Uiso 1 1 calc R U . . .
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
-1 6 -1 0.055
0 4 4 0.0525
0 -6 2 0.0757
3 -6 0 0.0674
5 -1 0 0.0887
5 0 -3 0.0947
0 0 7 0.026
0 0 -7 0.0283
-2 -3 -2 0.0761
-5 0 3 0.0919
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 117.15(12) . . ?
N3A N2A C9 113.2(6) . . ?
N2A N3A C12 114.2(5) . . ?
C18 C17 C9 122.6(19) . . ?
C18 C17 H17 118.7 . . ?
C9 C17 H17 118.7 . . ?
C12 C18 C17 124.6(19) . . ?
C12 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
N3B N2B C9 103.3(14) . . ?
N2B N3B C12 97.8(13) . . ?
C14 N4 C15 117.24(12) . . ?
O1 C1 C2 122.00(11) . . ?
O1 C1 C6 118.01(12) . . ?
C2 C1 C6 119.98(12) . . ?
C1 C2 C3 120.45(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.15(11) . . ?
O2 C3 C4 118.04(12) . . ?
C2 C3 C4 119.80(13) . . ?
C5 C4 C3 118.91(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.84(13) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.59(13) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 118.22(13) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 118.59(12) . . ?
C10 C9 C17 115.1(12) . . ?
C8 C9 C17 126.3(12) . . ?
C10 C9 N2A 115.3(3) . . ?
C8 C9 N2A 126.0(3) . . ?
C10 C9 N2B 150.3(5) . . ?
C8 C9 N2B 91.0(5) . . ?
C11 C10 C9 118.97(13) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.43(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C18 C12 C13 116.8(12) . . ?
C18 C12 C16 124.4(12) . . ?
C13 C12 C16 118.57(12) . . ?
C13 C12 N3A 115.0(3) . . ?
C16 C12 N3A 126.4(3) . . ?
C13 C12 N3B 154.8(4) . . ?
C16 C12 N3B 86.3(4) . . ?
C14 C13 C12 119.13(13) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
N4 C14 C13 123.88(13) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 122.88(13) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C12 118.30(13) . . ?
C15 C16 H16 120.9 . . ?
C12 C16 H16 120.9 . . ?
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 1.3599(16) . ?
O1 H1 0.82 . ?
O2 C3 1.3569(17) . ?
O2 H2A 0.82 . ?
N1 C11 1.3313(19) . ?
N1 C7 1.3359(18) . ?
N2A N3A 1.236(4) . ?
N2A C9 1.460(6) . ?
N3A C12 1.481(3) . ?
C17 C18 1.318(10) . ?
C17 C9 1.42(2) . ?
C17 H17 0.93 . ?
C18 C12 1.309(12) . ?
C18 H18 0.93 . ?
N2B N3B 1.242(10) . ?
N2B C9 1.536(16) . ?
N3B C12 1.650(16) . ?
N4 C14 1.3311(19) . ?
N4 C15 1.3356(18) . ?
C1 C2 1.3843(18) . ?
C1 C6 1.3904(17) . ?
C2 C3 1.3901(18) . ?
C2 H2 0.93 . ?
C3 C4 1.3918(18) . ?
C4 C5 1.378(2) . ?
C4 H4 0.93 . ?
C5 C6 1.382(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.379(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C10 1.3784(19) . ?
C10 C11 1.3725(19) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.367(2) . ?
C12 C16 1.393(2) . ?
C13 C14 1.366(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.3877(19) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
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 0.82 1.95 2.7688(14) 176.7 . yes
O2 H2A N4 0.82 1.97 2.7861(14) 177.1 2_667 yes
