#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558231.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_1558231
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            'C17.03 H15.03 N2.97 O2'
_chemical_formula_weight         293.29
_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             2020-03-05T13:03:00-00:00
_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                93.6858(16)
_cell_angle_beta                 106.6746(17)
_cell_angle_gamma                113.951(2)
_cell_formula_units_Z            2
_cell_length_a                   8.06741(16)
_cell_length_b                   9.8484(2)
_cell_length_c                   10.8930(2)
_cell_measurement_reflns_used    10527
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      75.103
_cell_measurement_theta_min      4.3
_cell_volume                     741.35(3)
_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 0.987
_diffrn_measured_fraction_theta_max 0.932
_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      0.1310714
_diffrn_orient_matrix_UB_12      -0.0768257
_diffrn_orient_matrix_UB_13      0.0521445
_diffrn_orient_matrix_UB_21      0.0232978
_diffrn_orient_matrix_UB_22      0.0588304
_diffrn_orient_matrix_UB_23      0.1413733
_diffrn_orient_matrix_UB_31      -0.1782397
_diffrn_orient_matrix_UB_32      -0.1457368
_diffrn_orient_matrix_UB_33      -0.0078161
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20462
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.174
_diffrn_reflns_theta_min         4.33
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.501
_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 light yellow'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0055(9)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0404
_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)+(0.0590P)²+0.1058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0
_reflns_number_gt                2327
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A50_BE50_270
_cod_original_cell_volume        741.36(3)
_cod_database_code               1558231
_shelx_estimated_absorpt_t_min   0.87
_shelx_estimated_absorpt_t_max   0.93
_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 0.16629(15) 0.15689(13) 0.30927(10) 0.0611(3) Uani 1 1 d . . . . .
H1 H 0.196615 0.179681 0.388969 0.092 Uiso 1 1 calc R U . . .
O2 O 0.82063(16) 0.22537(15) 0.43234(11) 0.0703(4) Uani 1 1 d . . . . .
H2A H 0.825112 0.263141 0.50325 0.105 Uiso 1 1 calc R U . . .
N1 N 0.25979(19) 0.24757(16) 0.57514(12) 0.0596(3) Uani 1 1 d . . . . .
N2A N 0.225(3) 0.3794(17) 0.9440(14) 0.0502(18) Uani 0.405(3) 1 d D U P A 1
N3A N 0.272(3) 0.5129(17) 0.9898(15) 0.051(2) Uani 0.405(3) 1 d D U P A 1
C17 C 0.209(3) 0.3775(16) 0.9348(13) 0.0498(17) Uani 0.515(3) 1 d D U P A 2
H17 H 0.152183 0.300667 0.975978 0.06 Uiso 0.515(3) 1 calc DR U P A 2
C18 C 0.260(3) 0.5193(16) 0.9828(14) 0.0473(14) Uani 0.515(3) 1 d D U P A 2
H18 H 0.312864 0.596 0.940118 0.057 Uiso 0.515(3) 1 calc R U P A 2
N2B N 0.273(3) 0.468(2) 0.9229(16) 0.052(2) Uani 0.081(2) 1 d D U P A 3
N3B N 0.194(2) 0.407(2) 1.0005(16) 0.054(2) Uani 0.081(2) 1 d D U P A 3
N4 N 0.17715(18) 0.65048(15) 1.33036(12) 0.0566(3) Uani 1 1 d . . . . .
C1 C 0.3171(2) 0.15322(15) 0.27969(13) 0.0486(3) Uani 1 1 d . . . . .
C2 C 0.4932(2) 0.18968(16) 0.37549(13) 0.0493(3) Uani 1 1 d . . . . .
H2 H 0.509614 0.216187 0.463148 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6453(2) 0.18692(16) 0.34155(14) 0.0527(4) Uani 1 1 d . . . . .
C4 C 0.6201(3) 0.14465(18) 0.21087(15) 0.0597(4) Uani 1 1 d . . . . .
H4 H 0.720339 0.140749 0.187227 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4445(3) 0.10867(18) 0.11702(14) 0.0622(4) Uani 1 1 d . . . . .
H5 H 0.427745 0.08124 0.029426 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2923(2) 0.11210(17) 0.14911(14) 0.0581(4) Uani 1 1 d . . . . .
H6 H 0.174738 0.087154 0.084011 0.07 Uiso 1 1 calc R U . . .
C7 C 0.3221(2) 0.39476(19) 0.62429(16) 0.0614(4) Uani 1 1 d . . . . .
H7 H 0.370398 0.465348 0.575431 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3185(2) 0.44702(19) 0.74334(15) 0.0590(4) Uani 1 1 d . . . . .
H8 H 0.36507 0.55044 0.77434 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2442(2) 0.34279(18) 0.81608(13) 0.0511(3) Uani 1 1 d D . . . .
C10 C 0.1835(2) 0.19147(18) 0.76715(15) 0.0582(4) Uani 1 1 d . . . . .
H10 H 0.135644 0.118483 0.814247 0.07 Uiso 1 1 calc R U . . .
C11 C 0.1945(2) 0.14967(19) 0.64819(15) 0.0605(4) Uani 1 1 d . . . . .
H11 H 0.154108 0.047227 0.616983 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2318(2) 0.55360(18) 1.10598(13) 0.0521(4) Uani 1 1 d D . . . .
C13 C 0.2857(2) 0.70406(19) 1.14992(16) 0.0611(4) Uani 1 1 d . . . . .
H13 H 0.341481 0.77632 1.104625 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2568(2) 0.74699(19) 1.26086(16) 0.0621(4) Uani 1 1 d . . . . .
H14 H 0.295182 0.849662 1.289318 0.075 Uiso 1 1 calc R U . . .
C15 C 0.1228(2) 0.50374(19) 1.28759(15) 0.0573(4) Uani 1 1 d . . . . .
H15 H 0.065382 0.434067 1.334211 0.069 Uiso 1 1 calc R U . . .
C16 C 0.1480(2) 0.45053(18) 1.17666(15) 0.0577(4) Uani 1 1 d . . . . .
H16 H 0.109426 0.347455 1.150137 0.069 Uiso 1 1 calc DR 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
-4 -2 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -5 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171
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 116.86(13) . . ?
N3A N2A C9 118.7(12) . . ?
N2A N3A C12 121.2(12) . . ?
C18 C17 C9 118.4(11) . . ?
C18 C17 H17 120.8 . . ?
C9 C17 H17 120.8 . . ?
C17 C18 C12 117.9(11) . . ?
C17 C18 H18 121 . . ?
C12 C18 H18 121 . . ?
N3B N2B C9 108.9(18) . . ?
N2B N3B C12 103.2(16) . . ?
C14 N4 C15 117.11(13) . . ?
O1 C1 C2 122.06(12) . . ?
O1 C1 C6 118.29(13) . . ?
C2 C1 C6 119.65(14) . . ?
C1 C2 C3 120.53(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.07(12) . . ?
O2 C3 C4 118.06(14) . . ?
C2 C3 C4 119.87(14) . . ?
C5 C4 C3 118.90(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.93(13) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.12(15) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.45(15) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 118.81(15) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 117.94(14) . . ?
C10 C9 C17 116.4(6) . . ?
C8 C9 C17 125.4(6) . . ?
C10 C9 N2A 116.4(6) . . ?
C8 C9 N2A 125.7(6) . . ?
C10 C9 N2B 149.9(6) . . ?
C8 C9 N2B 92.2(6) . . ?
C11 C10 C9 119.30(15) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N1 C11 C10 123.60(15) . . ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C13 C12 C16 117.90(14) . . ?
C13 C12 N3A 117.8(6) . . ?
C16 C12 N3A 124.3(6) . . ?
C13 C12 C18 114.9(6) . . ?
C16 C12 C18 127.1(6) . . ?
C13 C12 N3B 154.5(5) . . ?
C16 C12 N3B 87.4(5) . . ?
C14 C13 C12 119.46(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.78(15) . . ?
N4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N4 C15 C16 122.89(15) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C12 C16 C15 118.86(15) . . ?
C12 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
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 1.3581(17) . ?
O1 H1 0.82 . ?
O2 C3 1.3553(18) . ?
O2 H2A 0.82 . ?
N1 C11 1.329(2) . ?
N1 C7 1.340(2) . ?
N2A N3A 1.234(8) . ?
N2A C9 1.483(11) . ?
N3A C12 1.465(13) . ?
C17 C18 1.308(7) . ?
C17 C9 1.449(11) . ?
C17 H17 0.93 . ?
C18 C12 1.466(11) . ?
C18 H18 0.93 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.532(19) . ?
N3B C12 1.649(19) . ?
N4 C14 1.329(2) . ?
N4 C15 1.334(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.3871(19) . ?
C2 C3 1.389(2) . ?
C2 H2 0.93 . ?
C3 C4 1.389(2) . ?
C4 C5 1.376(2) . ?
C4 H4 0.93 . ?
C5 C6 1.382(2) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.377(2) . ?
C7 H7 0.93 . ?
C8 C9 1.385(2) . ?
C8 H8 0.93 . ?
C9 C10 1.379(2) . ?
C10 C11 1.372(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.371(2) . ?
C12 C16 1.386(2) . ?
C13 C14 1.367(2) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.387(2) . ?
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 1.94 2.7606(16) 174.8 . yes
O2 H2A N4 0.82 1.96 2.7796(16) 177.4 2_667 yes
